Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2741)
Drug Name
VS-12343
Synonyms
Hesperetin 7-O-rutinoside; LMPK12140451; MCULE-6401179754; QUQPHWDTPGMPEX-SGHBVPQBSA-N; STK801624; Hesperetin-7-O-rutinoside; hesperidin; (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside; 520-26-3; AB0013409; AKOS004119862; AKOS016357494; Flavanone, 3',5,7-trihydroxy-4'-methoxy-, 7-(6-O-.alpha.-L-rhamnosyl-D-glucoside); H6243; H992; ALBB-028539; BBL033922; SCHEMBL13886768
Indication Sickle-cell anaemia [ICD11: 3A51] Investigative [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 610.6 Topological Polar Surface Area 234
Heavy Atom Count 43 Rotatable Bond Count 7
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 15
Cross-matching ID
PubChem CID
16394497
CAS Number
520-26-3
Formula
C28H34O15
Canonical SMILES
CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
InChI
1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10?,17-,19?,21?,22?,23?,24?,25?,26?,27?,28?/m0/s1
InChIKey
QUQPHWDTPGMPEX-SGHBVPQBSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Hesperetin DM003395
72281
Oxidation - Deglycosylation 1 [3]
3-(3'-Hydroxy-4'-methoxyphenyl)-2-propionic acid DM004106 N. A. Unclear 2 [3]
3-(3'-Hydroxy-4'-methoxyphenyl)hydracrylic acid DM004117
62394529
Unclear 3 [3]
3-(3'-Hydroxy-4'-methoxyphenyl)propionic acid DM004107
2752054
Unclear 3 [3]
Caffeic acid DM003530
689043
Unclear 3 [3]
3'-Hydroxy-4'-methoxyphenylacetic acid DM004114
160562
Reduction - Dehydroxylation 4 [3]
3-(3',4'-dihydroxyphenyl)propionic acid DM002604
348154
Oxidation - Demethylation 4 [3]
3-(4'-Hydroxyyphenyl)-2-propionic acid DM004116 N. A. Unclear 4 [3]
(3,4-Dihydroxyphenyl)acetic acid DM000280
547
Unclear 5 [3]
3-(3'-Hydroxyphenyl)propionic acid DM004111
91
Reduction - Dehydroxylation 5 [3]
3-(4-Hydroxyphenyl) propionic acid DM003390
10394
Unclear 5 [3]
3-Hydroxy-4-methoxybenzoic acid DM004115
12575
Unclear 5 [3]
(4-Hydroxyphenyl) acetic acid DM001229
127
Unclear 6 [3]
3'-Hydroxyphenylacetic acid DM004109
12122
Unclear 6 [3]
3-Phenylpropionic acid DM003391
107
Reduction - Dehydroxylation 6 [3]
Protocatechuate DM002607
72
Unclear 6 [3]
3-Hydroxybenzoic acid DM004110
7420
Unclear 7 [3]
4-Hydroxybenzoic acid DM004023
135
Unclear 7 [3]
Phenyl acetic acid DM001228
999
Unclear 7 [3]
Midostaurin Metabolite P6 DM001360
243
Unclear 8 [3]
⏷ Show the Full List of 20  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004484 VS-12343 Hesperetin Oxidation - Deglycosylation Unclear [3]
MR004485 Hesperetin 3-(3'-Hydroxy-4'-methoxyphenyl)-2-propionic acid Unclear Unclear [3]
MR004486 3-(3'-Hydroxy-4'-methoxyphenyl)-2-propionic acid 3-(3'-Hydroxy-4'-methoxyphenyl)propionic acid Unclear Unclear [3]
MR004505 3-(3'-Hydroxy-4'-methoxyphenyl)-2-propionic acid Caffeic acid Unclear Unclear [3]
MR004507 3-(3'-Hydroxy-4'-methoxyphenyl)-2-propionic acid 3-(3'-Hydroxy-4'-methoxyphenyl)hydracrylic acid Unclear Unclear [3]
MR004487 3-(3'-Hydroxy-4'-methoxyphenyl)propionic acid 3-(3',4'-Dihydroxyphenyl)propionic acid Oxidation - Demethylation Unclear [3]
MR004503 3-(3'-Hydroxy-4'-methoxyphenyl)propionic acid 3'-Hydroxy-4'-methoxyphenylacetic acid Reduction - Dehydroxylation Unclear [3]
MR004506 Caffeic acid 3-(4'-Hydroxyyphenyl)-2-propionic acid Unclear Unclear [3]
MR004504 3'-Hydroxy-4'-methoxyphenylacetic acid 3-Hydroxy-4-methoxybenzoic acid Unclear Unclear [3]
MR004488 3-(3',4'-Dihydroxyphenyl)propionic acid 3'-4'-Dihydroxyphenylacetic acid Unclear Unclear [3]
MR004496 3-(3',4'-Dihydroxyphenyl)propionic acid 3-(3'-Hydroxyphenyl)propionic acid Reduction - Dehydroxylation Unclear [3]
MR004500 3-(3',4'-Dihydroxyphenyl)propionic acid 3-(4'-Hydroxyphenyl)propionic acid Unclear Unclear [3]
MR004489 3'-4'-Dihydroxyphenylacetic acid 3'-Hydroxyphenylacetic acid Unclear Unclear [3]
MR004494 3'-4'-Dihydroxyphenylacetic acid 3,4-Dihydroxybenzoic acid Unclear Unclear [3]
MR004497 3-(3'-Hydroxyphenyl)propionic acid 3-(phenyl)propionic acid Reduction - Dehydroxylation Unclear [3]
MR004499 3-(3'-Hydroxyphenyl)propionic acid 3'-Hydroxyphenylacetic acid Unclear Unclear [3]
MR004501 3-(4'-Hydroxyphenyl)propionic acid 4'-Hydroxyphenylacetic acid Unclear Unclear [3]
MR004490 3'-Hydroxyphenylacetic acid Phenylacetic acid Unclear Unclear [3]
MR004492 3'-Hydroxyphenylacetic acid 3-Hydroxybenzoic acid Unclear Unclear [3]
MR004495 3,4-Dihydroxybenzoic acid 3-Hydroxybenzoic acid Unclear Unclear [3]
MR004498 3-(phenyl)propionic acid Phenylacetic acid Unclear Unclear [3]
MR004502 4'-Hydroxyphenylacetic acid 4-Hydroxybenzoic acid Unclear Unclear [3]
MR004493 3-Hydroxybenzoic acid Benzoic acid Unclear Unclear [3]
MR004491 Phenylacetic acid Benzoic acid Unclear Unclear [3]
⏷ Show the Full List of 24 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alpha-L-rhamnosidase (lrA) DME1929 Lactobacillus rhamnosus
A0A179YH30_LACRH
3.2.1.40
[2]
References
1 Hesperetin and its sulfate and glucuronide metabolites inhibit TNF-alpha induced human aortic endothelial cell migration and decrease plasminogen activator inhibitor-1 (PAI-1) levels. Food Funct. 2016 Jan;7(1):118-26.
2 Catabolism of citrus flavanones by the probiotics Bifidobacterium longum and Lactobacillus rhamnosus. Eur J Nutr. 2018 Feb;57(1):231-242.
3 Biotransformation of two citrus flavanones by lactic acid bacteria in chemical defined medium

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