benzoic acid CDK 09051816002D 9 9 0 0 0 0 0 0 0 0999 V2000 2.9228 0.5075 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6238 -0.2425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3248 0.5075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9748 -0.2433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2738 0.5067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2733 2.0075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9738 2.7583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3252 2.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6238 -1.7425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 3 8 1 0 0 0 0 1 2 1 0 0 0 0 2 9 2 0 0 0 0 2 3 1 0 0 0 0 M END > InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9) > WPYMKLBDIGXBTP-UHFFFAOYSA-N > C7H6O2 > 122.036779432 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2 Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N Biotransformation_4 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O2/c12-11-7-6-10(13-11)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2 Precursor InChIKey: OJKCYERWEGKEIS-UHFFFAOYSA-N Biotransformation_5 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O3/c12-10(6-7-11(13)14)8-9-4-2-1-3-5-9/h1-5,10,12H,6-8H2,(H,13,14) Precursor InChIKey: OTIPOAGPXXBSSB-UHFFFAOYSA-N Biotransformation_6 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1314) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C11H14O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,12,13) Precursor InChIKey: BYHDDXPKOZIZRV-UHFFFAOYSA-N Biotransformation_7 Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11) Precursor InChIKey: XMIIGOLPHOKFCH-UHFFFAOYSA-N $$$$ 4-HYDROXYBENZOIC ACID CDK 09051816002D 10 10 0 0 0 0 0 0 0 0999 V2000 -2.2915 1.3193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9888 2.0629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3065 1.3065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6056 2.0565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8901 1.3316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9156 -0.2125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2207 -0.9518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6165 -0.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2920 -0.1684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9814 3.5628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 8 9 2 0 0 0 0 3 9 1 0 0 0 0 1 2 1 0 0 0 0 2 10 2 0 0 0 0 2 3 1 0 0 0 0 M END > InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) > FJKROLUGYXJWQN-UHFFFAOYSA-N > C7H6O3 > 138.03169405199998 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2 Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N Biotransformation_4 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-8(2-4-9)7-10(13)5-6-11(14)15/h1-4,10,12-13H,5-7H2,(H,14,15) Precursor InChIKey: JCHZTLFRWGBCDD-UHFFFAOYSA-N Biotransformation_5 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1314) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C11H14O3/c12-10-7-5-9(6-8-10)3-1-2-4-11(13)14/h5-8,12H,1-4H2,(H,13,14) Precursor InChIKey: YSSJQFONKASLKM-UHFFFAOYSA-N Biotransformation_6 Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12) Precursor InChIKey: NMHMNPHRMNGLLB-UHFFFAOYSA-N $$$$ 3-Hydroxybenzoic acid CDK 09051816002D 10 10 0 0 0 0 0 0 0 0999 V2000 -0.3206 2.8100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3208 1.3100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.5598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2781 1.3098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5681 0.5598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5681 -0.9402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2781 -1.6902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2806 -3.1902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.9402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6200 0.5602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 3 9 1 0 0 0 0 1 2 1 0 0 0 0 2 10 2 0 0 0 0 2 3 1 0 0 0 0 M END > InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10) > IJFXRHURBJZNAO-UHFFFAOYSA-N > C7H6O3 > 138.03169405199998 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2 Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N Biotransformation_4 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-2-8(6-9)7-10(13)4-5-11(14)15/h1-3,6,10,12-13H,4-5,7H2,(H,14,15) Precursor InChIKey: CBCIWEQMPVKOHC-UHFFFAOYSA-N Biotransformation_5 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1012) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C11H14O3/c12-10-6-3-5-9(8-10)4-1-2-7-11(13)14/h3,5-6,8,12H,1-2,4,7H2,(H,13,14) Precursor InChIKey: CMLIEOOXQFWANJ-UHFFFAOYSA-N Biotransformation_6 Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12) Precursor InChIKey: QVWAEZJXDYOKEH-UHFFFAOYSA-N $$$$ 5-benzyloxolan-2-one CDK 09051816002D 13 14 0 0 0 0 0 0 0 0999 V2000 2.9485 -3.1484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6494 -2.3984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0568 -2.1486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2808 -3.0122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9351 -2.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3044 -2.7485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5203 -1.8702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3670 -0.3772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9978 0.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7819 -0.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5233 -2.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4539 -0.7728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9524 -0.9336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 5 10 1 0 0 0 0 1 3 1 0 0 0 0 3 11 2 0 0 0 0 3 12 1 0 0 0 0 12 13 1 0 0 0 0 2 13 1 0 0 0 0 M END > InChI=1S/C11H12O2/c12-11-7-6-10(13-11)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2 > OJKCYERWEGKEIS-UHFFFAOYSA-N > C11H12O2 > 176.083729624 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2 Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N $$$$ 5-[(4-hydroxyphenyl)methyl]oxolan-2-one CDK 09051816002D 14 15 0 0 0 0 0 0 0 0999 V2000 4.0470 -2.6636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5470 -2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5071 -1.2436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6687 -3.8795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1765 -3.7268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6959 -4.9471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1652 -4.8186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8272 -3.4233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3213 -3.2903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9549 -2.2031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4205 -2.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9348 -0.7836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2970 -0.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0771 -1.2436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 5 11 1 0 0 0 0 1 3 1 0 0 0 0 3 12 2 0 0 0 0 3 13 1 0 0 0 0 13 14 1 0 0 0 0 2 14 1 0 0 0 0 M END > InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2 > OXASBXALVLRTKO-UHFFFAOYSA-N > C11H12O3 > 192.07864424399997 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N $$$$ 5-[(3-hydroxyphenyl)methyl]oxolan-2-one CDK 09051816002D 14 15 0 0 0 0 0 0 0 0999 V2000 3.2848 -1.9051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7848 -1.9051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7448 -0.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9065 -3.1210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5857 -2.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4648 -4.1848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9488 -4.0286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5628 -2.6601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6929 -1.4477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3093 -0.0802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1998 -1.5998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1725 -0.0251 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5348 0.4049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3148 -0.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 9 11 2 0 0 0 0 5 11 1 0 0 0 0 1 3 1 0 0 0 0 3 12 2 0 0 0 0 3 13 1 0 0 0 0 13 14 1 0 0 0 0 2 14 1 0 0 0 0 M END > InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2 > VYWFHBSBNKNWSB-UHFFFAOYSA-N > C11H12O3 > 192.078644244 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N $$$$ 4-Hydroxyhippuric acid CDK 09051816002D 14 14 0 0 0 0 0 0 0 0999 V2000 -3.8922 3.7647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3039 3.7391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5992 2.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8982 3.7328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1827 3.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2082 1.4638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5134 0.7245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9092 0.7138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5847 1.5079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3112 5.2391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5969 3.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6043 1.5084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2942 3.7519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0011 2.9956 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 8 9 2 0 0 0 0 3 9 1 0 0 0 0 2 10 2 0 0 0 0 2 3 1 0 0 0 0 1 11 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 13 14 1 0 0 0 0 14 2 1 0 0 0 0 M END > InChI=1S/C9H9NO4/c11-7-3-1-6(2-4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13) > ZMHLUFWWWPBTIU-UHFFFAOYSA-N > C9H9NO4 > 195.05315776799998 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2 Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N Biotransformation_4 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-8(2-4-9)7-10(13)5-6-11(14)15/h1-4,10,12-13H,5-7H2,(H,14,15) Precursor InChIKey: JCHZTLFRWGBCDD-UHFFFAOYSA-N Biotransformation_5 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1314) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C11H14O3/c12-10-7-5-9(6-8-10)3-1-2-4-11(13)14/h5-8,12H,1-4H2,(H,13,14) Precursor InChIKey: YSSJQFONKASLKM-UHFFFAOYSA-N Biotransformation_6 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1314) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12) Precursor InChIKey: NMHMNPHRMNGLLB-UHFFFAOYSA-N Biotransformation_7 Reaction Type: Glycination of aromatic acid (BTMR0206) Enzyme(s): EC 2.3.1.13 Precursor InChI: InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) Precursor InChIKey: FJKROLUGYXJWQN-UHFFFAOYSA-N $$$$ 3-hydroxyhippuric acid CDK 09051816002D 14 14 0 0 0 0 0 0 0 0999 V2000 7.1421 -1.1318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9459 -1.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6468 -1.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6463 -3.3816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6482 -4.1238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9473 -3.3738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9518 -1.8816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2521 -1.1338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6523 -1.1308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9462 0.3690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8429 -1.8816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8427 -3.3816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5440 -1.1314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2449 -1.8812 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 3 9 1 0 0 0 0 2 10 2 0 0 0 0 2 3 1 0 0 0 0 1 11 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 13 14 1 0 0 0 0 14 2 1 0 0 0 0 M END > InChI=1S/C9H9NO4/c11-7-3-1-2-6(4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13) > XDOFWFNMYJRHEW-UHFFFAOYSA-N > C9H9NO4 > 195.053157768 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2 Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N Biotransformation_4 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-2-8(6-9)7-10(13)4-5-11(14)15/h1-3,6,10,12-13H,4-5,7H2,(H,14,15) Precursor InChIKey: CBCIWEQMPVKOHC-UHFFFAOYSA-N Biotransformation_5 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1012) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C11H14O3/c12-10-6-3-5-9(8-10)4-1-2-7-11(13)14/h3,5-6,8,12H,1-2,4,7H2,(H,13,14) Precursor InChIKey: CMLIEOOXQFWANJ-UHFFFAOYSA-N Biotransformation_6 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1012) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12) Precursor InChIKey: QVWAEZJXDYOKEH-UHFFFAOYSA-N Biotransformation_7 Reaction Type: Glycination of aromatic acid (BTMR0206) Enzyme(s): EC 2.3.1.13 Precursor InChI: InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10) Precursor InChIKey: IJFXRHURBJZNAO-UHFFFAOYSA-N $$$$ 5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one CDK 09051816002D 15 16 0 0 0 0 0 0 0 0999 V2000 4.3919 -3.8072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0929 -3.0572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5003 -2.8074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7242 -3.6710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5083 -2.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6616 -1.2997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5544 -0.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9236 -1.0360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1395 -0.1576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0768 -2.5290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4456 -3.1426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8609 -3.4073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9667 -3.1230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8974 -1.4317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3959 -1.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 M END > InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 > ZNXXWTPQHVLMQT-UHFFFAOYSA-N > C11H12O4 > 208.073558864 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N $$$$ CDK 09051816002D 15 15 0 0 0 0 0 0 0 0999 V2000 -1.3249 -1.5107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2953 2.9765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3175 -0.0107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3027 4.4764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6054 5.2200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6054 6.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8754 7.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2254 6.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5182 7.4807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2254 5.2200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8754 4.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6128 0.7457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0148 0.7329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0074 2.2329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5907 2.2201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 5 11 1 0 0 0 0 1 3 1 0 0 0 0 3 12 2 0 0 0 0 3 13 1 0 0 0 0 13 14 1 0 0 0 0 2 14 1 0 0 0 0 15 2 1 0 0 0 0 M END > InChI=1S/C11H14O4/c12-9-3-1-8(2-4-9)7-10(13)5-6-11(14)15/h1-4,10,12-13H,5-7H2,(H,14,15) > JCHZTLFRWGBCDD-UHFFFAOYSA-N > C11H14O4 > 210.089208928 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2 Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N $$$$ 4-Hydroxy-5-(3-hydroxyphenyl)valeric acid CDK 09051816002D 15 15 0 0 0 0 0 0 0 0999 V2000 -3.5708 -2.0610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6253 -2.0619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2719 -2.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9242 -2.8121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2234 -2.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2239 -0.5615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5184 0.1807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8174 -0.5693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8219 -2.0615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1222 -2.8093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5224 -2.8123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2722 -4.3112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9728 -2.0615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3261 -2.8117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6255 -0.5619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 9 11 2 0 0 0 0 5 11 1 0 0 0 0 1 3 1 0 0 0 0 3 12 2 0 0 0 0 3 13 1 0 0 0 0 13 14 1 0 0 0 0 2 14 1 0 0 0 0 15 2 1 0 0 0 0 M END > InChI=1S/C11H14O4/c12-9-3-1-2-8(6-9)7-10(13)4-5-11(14)15/h1-3,6,10,12-13H,4-5,7H2,(H,14,15) > CBCIWEQMPVKOHC-UHFFFAOYSA-N > C11H14O4 > 210.089208928 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2 Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N $$$$ 5-(3,4-dihydroxyphenyl)pentanoic acid CDK 09051816002D 15 15 0 0 0 0 0 0 0 0999 V2000 5.5563 2.7954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3602 2.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2573 2.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9389 2.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2379 2.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2374 4.2962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5365 5.0462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8360 4.2954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1350 5.0454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8365 2.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1356 2.0447 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5374 2.0445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2573 0.5454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9582 2.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6592 2.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 M END > InChI=1S/C11H14O4/c12-9-6-5-8(7-10(9)13)3-1-2-4-11(14)15/h5-7,12-13H,1-4H2,(H,14,15) > KTDWBJGUMIZRHU-UHFFFAOYSA-N > C11H14O4 > 210.089208928 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16) Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N $$$$ 5-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one CDK 09051816002D 16 17 0 0 0 0 0 0 0 0999 V2000 -1.8334 -1.5384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5343 -2.2884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9417 -2.5382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8343 -1.6746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0503 -2.5529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8970 -4.0459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1129 -4.9243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4821 -4.3096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6981 -5.1880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6354 -2.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0041 -2.2030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4195 -1.9383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4082 -2.2227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3388 -3.9140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8373 -3.7532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2199 -3.0816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 11 16 1 0 0 0 0 M END > InChI=1S/C12H14O4/c1-15-11-7-8(2-4-10(11)13)6-9-3-5-12(14)16-9/h2,4,7,9,13H,3,5-6H2,1H3 > GCIFEQYZDROELP-UHFFFAOYSA-N > C12H14O4 > 222.089208928 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: Catechol O-methylation (BTMR0212) Enzyme(s): EC 2.1.1.6 Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N $$$$ 5-(4-hydroxy-3-methoxyphenyl)pentanoic acid CDK 09051816002D 16 16 0 0 0 0 0 0 0 0999 V2000 -7.4346 2.7946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2384 2.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1356 3.5446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9394 3.5446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3596 2.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3592 1.2938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6582 0.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9577 1.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2568 0.5446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9582 2.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2574 3.5452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6592 3.5454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1356 5.0446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8365 2.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5375 3.5446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5563 2.7950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 11 16 1 0 0 0 0 M END > InChI=1S/C12H16O4/c1-16-11-8-9(6-7-10(11)13)4-2-3-5-12(14)15/h6-8,13H,2-5H2,1H3,(H,14,15) > JQQIWBPHESZYNN-UHFFFAOYSA-N > C12H16O4 > 224.104858992 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16) Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N Biotransformation_4 Reaction Type: Catechol O-methylation (BTMR0212) Enzyme(s): EC 2.1.1.6 Precursor InChI: InChI=1S/C11H14O4/c12-9-6-5-8(7-10(9)13)3-1-2-4-11(14)15/h5-7,12-13H,1-4H2,(H,14,15) Precursor InChIKey: KTDWBJGUMIZRHU-UHFFFAOYSA-N $$$$ 4-Hydroxy-(3',4'-dihydroxyphenyl)-valeric acid CDK 09051816002D 16 16 0 0 0 0 0 0 0 0999 V2000 5.5563 2.7954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3602 2.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2573 2.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9389 2.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2379 2.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2374 4.2962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5365 5.0462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8360 4.2954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1350 5.0454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8365 2.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1356 2.0447 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5374 2.0445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2573 0.5454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9582 2.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6592 2.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3602 4.2954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 16 2 1 0 0 0 0 M END > InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16) > JDBYFCLHVYVXCX-UHFFFAOYSA-N > C11H14O5 > 226.08412354799998 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N $$$$ 4-hydroxy-5-(4-hydroxy-3-methoxyphenyl)pentanoic acid CDK 09051816002D 17 17 0 0 0 0 0 0 0 0999 V2000 -7.4346 2.7946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2384 2.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1356 3.5446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9394 3.5446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3596 2.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3592 1.2938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6582 0.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9577 1.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2568 0.5446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9582 2.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2574 3.5452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6592 3.5454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1356 5.0446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8365 2.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5375 3.5446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2384 1.2946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5563 2.7950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 16 2 1 0 0 0 0 11 17 1 0 0 0 0 M END > InChI=1S/C12H16O5/c1-17-11-7-8(2-4-10(11)14)6-9(13)3-5-12(15)16/h2,4,7,9,13-14H,3,5-6H2,1H3,(H,15,16) > QEGYEIXJXIALOP-UHFFFAOYSA-N > C12H16O5 > 240.09977361199998 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Catechol O-methylation (BTMR0212) Enzyme(s): EC 2.1.1.6 Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16) Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N $$$$ CDK 09051816002D 18 19 0 0 0 0 0 0 0 0999 V2000 -2.7584 -2.0490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4594 -2.7990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8668 -3.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0907 -2.1851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1252 -3.0635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4908 -2.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6990 -3.2888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5748 -4.8281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8022 -5.6904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2091 -5.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9678 -4.5300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3332 -2.7332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2639 -4.4245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7624 -4.2637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3900 -5.9208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1626 -5.0586 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 7.2249 -3.9995 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3041 -3.8285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 5 11 1 0 0 0 0 1 3 1 0 0 0 0 3 12 2 0 0 0 0 3 13 1 0 0 0 0 13 14 1 0 0 0 0 2 14 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 18 2 0 0 0 0 16 9 1 0 0 0 0 M END > InChI=1S/C11H12O6S/c12-11-6-5-10(16-11)7-8-1-3-9(4-2-8)17-18(13,14)15/h1-4,10H,5-7H2,(H,13,14,15) > HWTHTKOQADEPQM-UHFFFAOYSA-N > C11H12O6S > 272.035459104 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: 4-OH sulfonation of phenolic compound (BTMR0197) Enzyme(s): EC 2.8.2.1 Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2 Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N $$$$ 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate CDK 09051816002D 18 19 0 0 0 0 0 0 0 0999 V2000 -3.5377 -2.7050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0377 -2.7050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9977 -4.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1593 -1.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3329 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2119 -0.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6959 -0.5814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3100 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4401 -3.1624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0565 -4.5299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9470 -3.0103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4254 -4.5849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7877 -5.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5677 -4.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1653 -6.0474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5489 -4.6798 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 6.0027 -4.3103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4375 -3.1840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 9 11 2 0 0 0 0 5 11 1 0 0 0 0 1 3 1 0 0 0 0 3 12 2 0 0 0 0 3 13 1 0 0 0 0 13 14 1 0 0 0 0 2 14 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 18 2 0 0 0 0 16 10 1 0 0 0 0 M END > InChI=1S/C11H12O6S/c12-11-5-4-9(16-11)6-8-2-1-3-10(7-8)17-18(13,14)15/h1-3,7,9H,4-6H2,(H,13,14,15) > DPRDYFJWDRNYAZ-UHFFFAOYSA-N > C11H12O6S > 272.035459104 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: 3-OH sulfonation of phenolic compound (BTMR0196) Enzyme(s): EC 2.8.2.1 Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2 Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N $$$$ CDK 09051816002D 20 22 0 0 1 0 0 0 0 0999 V2000 3.8989 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8989 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8989 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8913 3.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1575 3.7566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5113 3.0135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8002 3.7808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5189 1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1727 0.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 4 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 2 13 1 0 0 0 0 13 14 1 6 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 20 2 0 0 0 0 14 20 1 0 0 0 0 M END > InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,15-18H,7H2/t15-/m1/s1 > DHOUAADDXACZIT-OAHLLOKOSA-N > C15H12O5 > 272.068473484 > Biotransformation_1 Reaction Type: Oxidation of secondary alcohol to ketone (BTMR0079) Enzyme(s): CYP1A2 Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C15H12O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,15-19H,6H2/t15-/m1/s1 Precursor InChIKey: NTNWIYXAYIKFSF-OAHLLOKOSA-N $$$$ CDK 09051816002D 20 22 0 0 1 0 0 0 0 0999 V2000 3.8989 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8989 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8989 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8989 3.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1932 3.7436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4925 2.9940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4975 1.5019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7980 0.7545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1982 0.7506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 4 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 2 13 1 0 0 0 0 13 14 1 6 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 20 2 0 0 0 0 14 20 1 0 0 0 0 M END > InChI=1S/C15H12O5/c16-9-3-1-2-8(4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,15-18H,7H2/t15-/m1/s1 > BRLRJLJMFXZCJD-OAHLLOKOSA-N > C15H12O5 > 272.068473484 > Biotransformation_1 Reaction Type: Oxidation of secondary alcohol to ketone (BTMR0079) Enzyme(s): CYP1A2 Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C15H12O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,15-19H,6H2/t15-/m1/s1 Precursor InChIKey: NTNWIYXAYIKFSF-OAHLLOKOSA-N $$$$ SCHEMBL16151244 CDK 09051816002D 21 23 0 0 1 0 0 0 0 0999 V2000 3.8989 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8989 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8989 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1986 0.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4975 1.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4968 3.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7957 3.7508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 3.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 5.2512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8982 3.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 4 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 2 13 1 0 0 0 0 13 14 1 6 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 14 21 1 0 0 0 0 M END > InChI=1S/C15H12O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,15-19H,6H2/t15-/m1/s1 > NTNWIYXAYIKFSF-OAHLLOKOSA-N > C15H12O6 > 288.06338810399996 > Biotransformation_1 Reaction Type: Oxidation of secondary alcohol to ketone (BTMR0079) Enzyme(s): CYP1A2 Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N $$$$ Symplocosidin CDK 09051816002D 22 24 0 0 1 0 0 0 0 0999 V2000 3.8989 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8989 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8989 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1986 0.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4975 1.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4968 3.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7957 3.7508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 3.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 5.2512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8982 3.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4962 6.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 4 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 2 13 1 0 0 0 0 13 14 1 6 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 14 21 1 0 0 0 0 20 22 1 0 0 0 0 M END > InChI=1S/C16H16O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-6,13,16-20H,7H2,1H3/t13-,16-/m1/s1 > NJHJXXLBWQXMRO-CZUORRHYSA-N > C16H16O6 > 304.09468823199995 > Biotransformation_1 Reaction Type: Catechol O-methylation (BTMR0212) Enzyme(s): EC 2.1.1.6 Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N $$$$ 6-(4-carboxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid CDK 09051816002D 22 23 0 0 0 0 0 0 0 0999 V2000 -5.5979 6.8408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8606 5.5345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3607 5.5199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6045 6.8153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1295 6.8228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3418 5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1582 5.4996 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0980 4.1990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6420 4.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6232 4.2428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9127 4.2032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1627 2.8832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9127 1.5832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4027 1.5832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1492 0.2821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1627 2.8832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6627 2.8782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4027 4.2032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1535 5.5018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1625 0.2843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9123 -1.0149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3375 0.2845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 8 9 2 0 0 0 0 3 9 1 0 0 0 0 1 2 1 0 0 0 0 2 10 2 0 0 0 0 2 3 1 0 0 0 0 11 7 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 11 18 1 0 0 0 0 18 19 1 0 0 0 0 13 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 M END > InChI=1S/C13H14O9/c14-7-8(15)10(12(19)20)22-13(9(7)16)21-6-3-1-5(2-4-6)11(17)18/h1-4,7-10,13-16H,(H,17,18)(H,19,20) > DKNOHNCMCYDVLT-UHFFFAOYSA-N > C13H14O9 > 314.063782028 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2 Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N Biotransformation_4 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-8(2-4-9)7-10(13)5-6-11(14)15/h1-4,10,12-13H,5-7H2,(H,14,15) Precursor InChIKey: JCHZTLFRWGBCDD-UHFFFAOYSA-N Biotransformation_5 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1314) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C11H14O3/c12-10-7-5-9(6-8-10)3-1-2-4-11(13)14/h5-8,12H,1-4H2,(H,13,14) Precursor InChIKey: YSSJQFONKASLKM-UHFFFAOYSA-N Biotransformation_6 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1314) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12) Precursor InChIKey: NMHMNPHRMNGLLB-UHFFFAOYSA-N Biotransformation_7 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) Precursor InChIKey: FJKROLUGYXJWQN-UHFFFAOYSA-N $$$$ 3,4,5-trihydroxy-6-(4-hydroxybenzoyloxy)oxane-2-carboxylic acid CDK 09051816002D 22 23 0 0 0 0 0 0 0 0999 V2000 1.2769 1.8179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2821 0.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0143 -0.4366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0018 -1.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2655 -2.6972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6217 -1.9585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9081 -2.7300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6342 -0.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2906 0.3027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5837 -0.4276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5734 2.5723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8934 1.8223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1934 2.5723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1934 4.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4944 4.8088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8934 4.8223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8983 6.3223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5734 4.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2748 4.8131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4923 1.8221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7914 2.5719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4920 0.3221 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 8 9 2 0 0 0 0 3 9 1 0 0 0 0 1 2 1 0 0 0 0 2 10 2 0 0 0 0 2 3 1 0 0 0 0 1 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 11 18 1 0 0 0 0 18 19 1 0 0 0 0 13 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 M END > InChI=1S/C13H14O9/c14-6-3-1-5(2-4-6)12(20)22-13-9(17)7(15)8(16)10(21-13)11(18)19/h1-4,7-10,13-17H,(H,18,19) > UDDPEWPRKBWBMA-UHFFFAOYSA-N > C13H14O9 > 314.063782028 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2 Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N Biotransformation_4 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-8(2-4-9)7-10(13)5-6-11(14)15/h1-4,10,12-13H,5-7H2,(H,14,15) Precursor InChIKey: JCHZTLFRWGBCDD-UHFFFAOYSA-N Biotransformation_5 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1314) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C11H14O3/c12-10-7-5-9(6-8-10)3-1-2-4-11(13)14/h5-8,12H,1-4H2,(H,13,14) Precursor InChIKey: YSSJQFONKASLKM-UHFFFAOYSA-N Biotransformation_6 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1314) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12) Precursor InChIKey: NMHMNPHRMNGLLB-UHFFFAOYSA-N Biotransformation_7 Reaction Type: O-glucuronidation of aromatic acid (BTMR0168) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) Precursor InChIKey: FJKROLUGYXJWQN-UHFFFAOYSA-N $$$$ 6-(3-carboxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid CDK 09051816002D 22 23 0 0 0 0 0 0 0 0999 V2000 -4.5539 5.1482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2536 4.4003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9558 5.1524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9580 6.6532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6648 7.3977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6356 6.6500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6427 5.1579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9444 4.4124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6555 4.4047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2512 2.9003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9495 2.9124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6400 2.1442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6395 0.6434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9299 -0.1016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9258 -1.6016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2381 0.6442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5346 -0.1101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2399 2.1674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5394 2.9166 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6596 -0.1064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6599 -1.6064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9585 0.6438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 3 9 1 0 0 0 0 1 2 1 0 0 0 0 2 10 2 0 0 0 0 2 3 1 0 0 0 0 11 8 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 11 18 1 0 0 0 0 18 19 1 0 0 0 0 13 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 M END > InChI=1S/C13H14O9/c14-7-8(15)10(12(19)20)22-13(9(7)16)21-6-3-1-2-5(4-6)11(17)18/h1-4,7-10,13-16H,(H,17,18)(H,19,20) > ZXNABXFYKZWAPQ-UHFFFAOYSA-N > C13H14O9 > 314.063782028 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2 Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N Biotransformation_4 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-2-8(6-9)7-10(13)4-5-11(14)15/h1-3,6,10,12-13H,4-5,7H2,(H,14,15) Precursor InChIKey: CBCIWEQMPVKOHC-UHFFFAOYSA-N Biotransformation_5 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1012) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C11H14O3/c12-10-6-3-5-9(8-10)4-1-2-7-11(13)14/h3,5-6,8,12H,1-2,4,7H2,(H,13,14) Precursor InChIKey: CMLIEOOXQFWANJ-UHFFFAOYSA-N Biotransformation_6 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1012) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12) Precursor InChIKey: QVWAEZJXDYOKEH-UHFFFAOYSA-N Biotransformation_7 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10) Precursor InChIKey: IJFXRHURBJZNAO-UHFFFAOYSA-N $$$$ 3,4,5-trihydroxy-6-(3-hydroxybenzoyloxy)oxane-2-carboxylic acid CDK 09051816002D 22 23 0 0 0 0 0 0 0 0999 V2000 1.2847 1.7721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2899 0.2722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0066 -0.4823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0016 -1.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2934 -2.7300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5952 -1.9847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6051 -0.4925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9081 0.2506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3083 0.2630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5915 -0.4734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5812 2.5266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9012 1.7766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2012 2.5266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2012 4.0166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5022 4.7631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9012 4.7766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9061 6.2766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5812 4.0166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2826 4.7674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5001 1.7764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7992 2.5262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4998 0.2764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 3 9 1 0 0 0 0 1 2 1 0 0 0 0 2 10 2 0 0 0 0 2 3 1 0 0 0 0 1 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 11 18 1 0 0 0 0 18 19 1 0 0 0 0 13 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 M END > InChI=1S/C13H14O9/c14-6-3-1-2-5(4-6)12(20)22-13-9(17)7(15)8(16)10(21-13)11(18)19/h1-4,7-10,13-17H,(H,18,19) > NAPPBXXQXKMDNU-UHFFFAOYSA-N > C13H14O9 > 314.063782028 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2 Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N Biotransformation_4 Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-2-8(6-9)7-10(13)4-5-11(14)15/h1-3,6,10,12-13H,4-5,7H2,(H,14,15) Precursor InChIKey: CBCIWEQMPVKOHC-UHFFFAOYSA-N Biotransformation_5 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1012) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C11H14O3/c12-10-6-3-5-9(8-10)4-1-2-7-11(13)14/h3,5-6,8,12H,1-2,4,7H2,(H,13,14) Precursor InChIKey: CMLIEOOXQFWANJ-UHFFFAOYSA-N Biotransformation_6 Reaction Type: Beta-oxidation of carboxylic acid (BTMR1012) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12) Precursor InChIKey: QVWAEZJXDYOKEH-UHFFFAOYSA-N Biotransformation_7 Reaction Type: O-glucuronidation of aromatic acid (BTMR0168) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10) Precursor InChIKey: IJFXRHURBJZNAO-UHFFFAOYSA-N $$$$ CDK 09051816002D 26 28 0 0 0 0 0 0 0 0999 V2000 -1.4073 -0.3180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0446 -0.9451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4188 -1.4156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2616 -0.2078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2762 1.2921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0192 2.0484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0267 3.5233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3017 4.3110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2965 5.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5971 3.5548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5642 2.0108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9081 -1.2366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 -2.7300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2114 -2.4316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5929 6.5655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9129 5.8155 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2129 6.5655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2129 8.0555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5140 8.8020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9129 8.8155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9179 10.3155 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5929 8.0555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2943 8.8063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5118 5.8153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8110 6.5651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5116 4.3153 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 5 11 1 0 0 0 0 1 3 1 0 0 0 0 3 12 2 0 0 0 0 3 13 1 0 0 0 0 13 14 1 0 0 0 0 2 14 1 0 0 0 0 15 9 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 15 22 1 0 0 0 0 22 23 1 0 0 0 0 17 24 1 0 0 0 0 24 25 1 0 0 0 0 24 26 2 0 0 0 0 M END > InChI=1S/C17H20O9/c18-11-6-5-10(24-11)7-8-1-3-9(4-2-8)25-17-14(21)12(19)13(20)15(26-17)16(22)23/h1-4,10,12-15,17,19-21H,5-7H2,(H,22,23) > FTDMUGVYLIJMHW-UHFFFAOYSA-N > C17H20O9 > 368.11073222 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2 Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N $$$$ 3,4,5-trihydroxy-6-{3-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylic acid CDK 09051816002D 26 28 0 0 0 0 0 0 0 0999 V2000 4.3890 5.4078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0194 6.0195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3881 6.5168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7216 5.2674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7240 3.7674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0248 3.0188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0230 1.5267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7253 0.7743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4294 1.5142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8670 0.7597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4263 3.0151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8793 6.3547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6461 7.8229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1693 7.5077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1686 1.5053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1791 3.0234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4786 3.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7690 3.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0660 3.7828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7772 1.5234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0787 0.7777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4590 0.7603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4599 -0.7397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4784 5.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7773 6.0244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1792 6.0240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 9 11 2 0 0 0 0 5 11 1 0 0 0 0 1 3 1 0 0 0 0 3 12 2 0 0 0 0 3 13 1 0 0 0 0 13 14 1 0 0 0 0 2 14 1 0 0 0 0 15 10 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 15 22 1 0 0 0 0 22 23 1 0 0 0 0 17 24 1 0 0 0 0 24 25 1 0 0 0 0 24 26 2 0 0 0 0 M END > InChI=1S/C17H20O9/c18-11-5-4-10(24-11)7-8-2-1-3-9(6-8)25-17-14(21)12(19)13(20)15(26-17)16(22)23/h1-3,6,10,12-15,17,19-21H,4-5,7H2,(H,22,23) > DPSUQBKEHXAIDY-UHFFFAOYSA-N > C17H20O9 > 368.11073222 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012) Enzyme(s): Unspecified bacterial dehydroxylase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2 Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N $$$$ 3,4,5-trihydroxy-6-{2-hydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carbox CDK 09051816002D 27 29 0 0 0 0 0 0 0 0999 V2000 7.7205 2.1961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3496 2.8050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7173 3.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0533 2.0503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7516 2.7956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7466 4.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4449 5.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1481 4.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1537 5.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1530 2.7854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1434 2.0309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4548 2.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2088 3.1479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9728 4.6116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4965 4.2935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4450 2.7764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4555 4.2946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7550 5.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0454 4.3004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3424 5.0539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0536 2.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3551 2.0489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7354 2.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7363 0.5314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7548 6.5454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0537 7.2956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4556 7.2952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 16 11 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 16 23 1 0 0 0 0 23 24 1 0 0 0 0 18 25 1 0 0 0 0 25 26 1 0 0 0 0 25 27 2 0 0 0 0 M END > InChI=1S/C17H20O10/c18-9-3-1-7(5-8-2-4-11(19)25-8)6-10(9)26-17-14(22)12(20)13(21)15(27-17)16(23)24/h1,3,6,8,12-15,17-18,20-22H,2,4-5H2,(H,23,24) > UVGDTVGPBRLMQY-UHFFFAOYSA-N > C17H20O10 > 384.10564683999996 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N $$$$ 3,4,5-trihydroxy-6-{2-hydroxy-4-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carbox CDK 09051816002D 27 29 0 0 0 0 0 0 0 0999 V2000 7.1503 2.9720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9925 4.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6109 2.6639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6909 5.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3944 4.4547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0923 5.2010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7959 4.4465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8015 2.9457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5051 2.1912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1036 2.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1086 0.6994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4001 2.9538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2185 1.2925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3686 3.9609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3551 5.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7965 2.9367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8070 4.4549 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1065 5.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3969 4.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6939 5.2142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4051 2.9549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7066 2.2092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0869 2.1917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1063 6.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4052 7.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8071 7.4555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 16 9 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 16 23 1 0 0 0 0 23 24 1 0 0 0 0 18 25 1 0 0 0 0 25 26 1 0 0 0 0 25 27 2 0 0 0 0 M END > InChI=1S/C17H20O10/c18-9-6-7(5-8-2-4-11(19)25-8)1-3-10(9)26-17-14(22)12(20)13(21)15(27-17)16(23)24/h1,3,6,8,12-15,17-18,20-22H,2,4-5H2,(H,23,24) > OTBJYBQGMPICIK-UHFFFAOYSA-N > C17H20O10 > 384.10564683999996 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N $$$$ 6-[5-(4-carboxy-2-hydroxybutyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carbox CDK 09051816002D 28 29 0 0 0 0 0 0 0 0999 V2000 11.6786 4.0497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4825 4.0309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3823 3.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1862 3.2762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8845 4.0215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8795 5.5224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5778 6.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2810 5.5122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0207 6.2575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2859 4.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0105 3.2568 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5877 3.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3877 1.7950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0806 4.0403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7843 3.2856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4771 5.5309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3121 4.0024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3226 5.5205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6221 6.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9125 5.5263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2095 6.2799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9207 4.0205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2222 3.2748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6025 3.2574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6034 1.7574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6219 7.7713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9208 8.5216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3227 8.5211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 16 2 1 0 0 0 0 17 11 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 17 24 1 0 0 0 0 24 25 1 0 0 0 0 19 26 1 0 0 0 0 26 27 1 0 0 0 0 26 28 2 0 0 0 0 M END > InChI=1S/C17H22O11/c18-8(2-4-11(20)21)5-7-1-3-9(19)10(6-7)27-17-14(24)12(22)13(23)15(28-17)16(25)26/h1,3,6,8,12-15,17-19,22-24H,2,4-5H2,(H,20,21)(H,25,26) > BKJQCPDRWDNBIN-UHFFFAOYSA-N > C17H22O11 > 402.116211524 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16) Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N $$$$ 6-[4-(4-carboxy-2-hydroxybutyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carbox CDK 09051816002D 28 29 0 0 0 0 0 0 0 0999 V2000 -6.6056 10.3403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0967 7.7578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8511 9.0439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3422 6.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1578 6.4665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9123 5.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4123 5.1743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1578 6.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6578 6.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4033 7.7743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1490 9.0758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9033 7.7691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5966 7.7423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3511 9.0491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5967 7.7526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3512 9.0594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4122 5.1856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6622 3.8656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4122 2.5656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9022 2.5656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6487 1.2646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6622 3.8656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1622 3.8607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9022 5.1856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6530 6.4842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6620 1.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4118 -0.0325 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1620 1.2669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 16 2 1 0 0 0 0 17 9 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 17 24 1 0 0 0 0 24 25 1 0 0 0 0 19 26 1 0 0 0 0 26 27 1 0 0 0 0 26 28 2 0 0 0 0 M END > InChI=1S/C17H22O11/c18-8(2-4-11(20)21)5-7-1-3-10(9(19)6-7)27-17-14(24)12(22)13(23)15(28-17)16(25)26/h1,3,6,8,12-15,17-19,22-24H,2,4-5H2,(H,20,21)(H,25,26) > LLKUARGHNZMSRT-UHFFFAOYSA-N > C17H22O11 > 402.116211524 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16) Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N $$$$ 6-{[5-(3,4-dihydroxyphenyl)-4-hydroxypentanoyl]oxy}-3,4,5-trihydroxyoxane-2-carb CDK 09051816002D 28 29 0 0 0 0 0 0 0 0999 V2000 0.3144 3.8187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5105 3.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6108 4.5732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8069 4.5911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1085 3.8456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1132 2.3448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4149 1.5993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7118 2.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0134 1.6091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7071 3.8554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0036 4.6097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4055 4.6009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6056 6.0732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9124 3.8277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2089 4.5821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5157 2.3366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9873 4.5642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9977 6.0824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2973 6.8332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5876 6.0882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8846 6.8417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5958 4.5824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8973 3.8367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2776 3.8192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2785 2.3192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2970 8.3332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5959 9.0834 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9979 9.0830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 5 12 1 0 0 0 0 1 3 1 0 0 0 0 3 13 2 0 0 0 0 3 14 1 0 0 0 0 14 15 1 0 0 0 0 2 15 1 0 0 0 0 16 2 1 0 0 0 0 17 1 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 17 24 1 0 0 0 0 24 25 1 0 0 0 0 19 26 1 0 0 0 0 26 27 1 0 0 0 0 26 28 2 0 0 0 0 M END > InChI=1S/C17H22O11/c18-8(5-7-1-3-9(19)10(20)6-7)2-4-11(21)27-17-14(24)12(22)13(23)15(28-17)16(25)26/h1,3,6,8,12-15,17-20,22-24H,2,4-5H2,(H,25,26) > FZTBEBWSWJPSHQ-UHFFFAOYSA-N > C17H22O11 > 402.116211524 > Biotransformation_1 Reaction Type: Flavan-3-ol C-ring fission (BTMR0256) Enzyme(s): Unspecified gut bacterial enzyme Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N Biotransformation_2 Reaction Type: Lactone Hydrolysis (BTMR0259) Enzyme(s): Unspecified bacterial lactonase Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N Biotransformation_3 Reaction Type: O-glucuronidation of aliphatic acid (BTMR0167) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16) Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N $$$$ CDK 09051816002D 33 36 0 0 1 0 0 0 0 0999 V2000 3.8989 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8989 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8989 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1986 0.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4975 1.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4968 3.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7957 3.7508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 3.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 5.2512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8982 3.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4962 6.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8136 5.2467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1161 5.9922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1213 7.4822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4249 8.2242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8239 8.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8341 9.7466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5013 7.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2053 8.2465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4125 5.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7142 5.9828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4070 3.7375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 4 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 2 13 1 0 0 0 0 13 14 1 6 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 14 21 1 0 0 0 0 22 20 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 22 29 1 0 0 0 0 29 30 1 0 0 0 0 24 31 1 0 0 0 0 31 32 1 0 0 0 0 31 33 2 0 0 0 0 M END > InChI=1S/C21H22O12/c22-8-4-11(24)9-6-12(25)18(31-13(9)5-8)7-1-2-10(23)14(3-7)32-21-17(28)15(26)16(27)19(33-21)20(29)30/h1-5,12,15-19,21-28H,6H2,(H,29,30)/t12-,15?,16?,17?,18-,19?,21?/m1/s1 > BUONZQIZWIITTB-FVNRAWLNSA-N > C21H22O12 > 466.11112614399997 > Biotransformation_1 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N $$$$ CDK 09051816002D 33 36 0 0 1 0 0 0 0 0999 V2000 3.8989 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8989 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8989 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1986 0.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4975 1.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4968 3.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7957 3.7508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 3.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 5.2512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8982 3.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0948 3.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1003 1.4829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3974 0.7278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6902 1.4685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9847 0.7107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7033 2.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0073 3.7157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3877 3.7418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3935 5.2418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3922 -0.7722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6886 -1.5267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0906 -1.5177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 4 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 2 13 1 0 0 0 0 13 14 1 6 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 14 21 1 0 0 0 0 22 18 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 22 29 1 0 0 0 0 29 30 1 0 0 0 0 24 31 1 0 0 0 0 31 32 1 0 0 0 0 31 33 2 0 0 0 0 M END > InChI=1S/C21H22O12/c22-8-4-10(23)9-6-12(25)18(31-14(9)5-8)7-1-2-13(11(24)3-7)32-21-17(28)15(26)16(27)19(33-21)20(29)30/h1-5,12,15-19,21-28H,6H2,(H,29,30)/t12-,15?,16?,17?,18-,19?,21?/m1/s1 > FXAMKGHSKXKNHR-FVNRAWLNSA-N > C21H22O12 > 466.11112614399997 > Biotransformation_1 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N $$$$ CDK 09051816002D 33 36 0 0 1 0 0 0 0 0999 V2000 3.8989 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8989 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8989 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1986 0.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4975 1.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4968 3.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7957 3.7508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 3.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 5.2512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8982 3.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1981 0.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5154 1.5052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8181 0.7599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8234 -0.7301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1272 -1.4719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5262 -1.4948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5366 -2.9948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2035 -0.7396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9076 -1.4950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1143 1.5148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4161 0.7697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1086 3.0148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 4 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 2 13 1 0 0 0 0 13 14 1 6 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 14 21 1 0 0 0 0 22 9 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 22 29 1 0 0 0 0 29 30 1 0 0 0 0 24 31 1 0 0 0 0 31 32 1 0 0 0 0 31 33 2 0 0 0 0 M END > InChI=1S/C21H22O12/c22-10-2-1-7(3-12(10)24)18-13(25)6-9-11(23)4-8(5-14(9)32-18)31-21-17(28)15(26)16(27)19(33-21)20(29)30/h1-5,13,15-19,21-28H,6H2,(H,29,30)/t13-,15?,16?,17?,18-,19?,21?/m1/s1 > FDWDKTKDGDLDTP-HUTRNBJCSA-N > C21H22O12 > 466.11112614399997 > Biotransformation_1 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N $$$$ CDK 09051816002D 33 36 0 0 1 0 0 0 0 0999 V2000 3.8989 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8989 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8989 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1986 0.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4975 1.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4968 3.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7957 3.7508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 3.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 5.2512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8982 3.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5990 -3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9164 -2.9954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2190 -3.7410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2242 -5.2309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5278 -5.9729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9268 -5.9954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9369 -7.4954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6042 -5.2400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3082 -5.9952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5153 -2.9863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8171 -3.7316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5099 -1.4863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 4 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 2 13 1 0 0 0 0 13 14 1 6 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 14 21 1 0 0 0 0 22 6 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 22 29 1 0 0 0 0 29 30 1 0 0 0 0 24 31 1 0 0 0 0 31 32 1 0 0 0 0 31 33 2 0 0 0 0 M END > InChI=1S/C21H22O12/c22-8-4-13-9(6-12(25)18(31-13)7-1-2-10(23)11(24)3-7)14(5-8)32-21-17(28)15(26)16(27)19(33-21)20(29)30/h1-5,12,15-19,21-28H,6H2,(H,29,30)/t12-,15?,16?,17?,18-,19?,21?/m1/s1 > KGLMKAPOVXBIJB-FVNRAWLNSA-N > C21H22O12 > 466.11112614399997 > Biotransformation_1 Reaction Type: Aromatic -OH glucuronidation (BTMR0166) Enzyme(s): EC 2.4.1.17 Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N $$$$