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

General Information of Drug (ID: DR3444)
Drug Name
Epigallocatechin gallate
Synonyms
(-)-Epigallocatechin gallate; EGCG; 989-51-5; Epigallocatechin 3-gallate; Epigallocatechin-3-gallate; Tea catechin; (-)-Epigallocatechin-3-o-gallate; Teavigo; Epigallocatechin-3-monogallate; (-)-Epigallocatechol gallate; (2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate; Catechin deriv; UNII-BQM438CTEL; Green tea extract; CCRIS 3729; (-)-epigallocatechin 3-gallate; C22H18O11; BQM438CTEL; (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl; EGCG analogs; EGCG, Anagen; Epigallocatechin gallate analogs, Anagen; Epigallocatechin gallate, Anagen; GTPs,Anagen; Green tea polyphenols, Anagen; EPIGALOCATECHIN GALLATE
Indication Hepatic fibrosis/cirrhosis [ICD11: DB93] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 458.4 Topological Polar Surface Area 197
Heavy Atom Count 33 Rotatable Bond Count 4
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 11
Cross-matching ID
PubChem CID
65064
ChEBI ID
CHEBI:4806
CAS Number
989-51-5
TTD Drug ID
D0U2BH
Formula
C22H18O11
Canonical SMILES
C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
InChI
InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
InChIKey
WMBWREPUVVBILR-WIYYLYMNSA-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
EGC DM003686
91460
Unclear 1 [2]
EGCG-4''-Sulfate DM017628 N. A. Unclear 1 [3]
GA DM015450
5360835
Unclear 1 [2]
1-(3',4',5'-trihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol DM016490
101785540
Unclear 2 [2]
1-(3',5'-dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol DM017626 N. A. Unclear 2 [2]
4'-Deoxy EGC DM016560
123539448
Unclear 2 [2]
Pyrogallol DM014842
1057
Unclear 2 [2]
1-(3',5'-dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol DM017626 N. A. Unclear 3 [2]
4-hydroxy-5-(3',4',5'-trihydroxyphenyl)valeric acid DM016564
124202073
Unclear 3 [2]
5-(3',5'-dihydroxyphenyl)valeric acid DM016492
101900150
Unclear 3 [2]
Catechol DM003935
289
Unclear 3 [2]
3-(3',5'-dihydroxyphenyl)propionic acid DM015220
161525
Unclear 4 [2]
5-(3',4',5'-trihydroxyphenyl)--valerolactone DM017625 N. A. Unclear 4 [2]
5-(3',4',5'-trihydroxyphenyl)valeric acid DM016491
101900149
Unclear 4 [2]
5-(3',5'-dihydroxyphenyl)--valerolactone DM016142
52920453
Unclear 4 [2]
5-(3',5'-dihydroxyphenyl)valeric acid DM016492
101900150
Unclear 4 [2]
(4-Hydroxyphenyl) acetic acid DM001229
127
Unclear 5 [2]
3-(3',5'-dihydroxyphenyl)propionic acid DM015220
161525
Unclear 5 [2]
5-(3',4'-dihydroxyphenyl)--valerolactone DM016107
45093073
Unclear 5 [2]
5-(3',5'-dihydroxyphenyl)--valerolactone DM016142
52920453
Unclear 5 [2]
5-(3',5'-dihydroxyphenyl)valeric acid DM016492
101900150
Unclear 5 [2]
4-Hydroxybenzoic acid DM004023
135
Unclear 6 [2]
5-(3',4'-dihydroxyphenyl)-propionic acid DM014818
547
Unclear 6 [2]
5-(3',5'-dihydroxyphenyl)valeric acid DM016492
101900150
Unclear 6 [2]
5-(3'-hydroxyphenyl)valeric acid DM016141
52920334
Unclear 6 [2]
Epigallocatechin gallate Metabolite 14 DM017627 N. A. Unclear 6 [4]
Vanillic acid DM014918
8468
Unclear 6 [2]
3'-Hydroxyphenylacetic acid DM004109
12122
Unclear 7 [2]
3-(3'-hydroxyphenyl)-propionic acid DM016108
45101756
Unclear 7 [2]
3-Hydroxybenzoic acid DM004110
7420
Unclear 7 [2]
5-(3',4'-dihydroxyphenyl)-propionic acid DM014818
547
Unclear 7 [2]
5-(3'-hydroxyphenyl)valeric acid DM016141
52920334
Unclear 7 [2]
Liquiritin metabolite M9 DM005503
10394
Unclear 7 [2]
Midostaurin Metabolite P6B DM001361
464
Unclear 7 [2]
3'-Hydroxyphenylacetic acid DM004109
12122
Unclear 8 [2]
3-Hydroxybenzoic acid DM004110
7420
Unclear 8 [2]
⏷ Show the Full List of 36  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013559 Epigallocatechin gallate EGC Unclear Unclear [2]
MR013585 Epigallocatechin gallate GA Unclear Unclear [2]
MR013589 Epigallocatechin gallate EGCG-4''-Sulfate Unclear SULT1A1 ... [3]
MR013560 EGC 1-(3',4',5'-trihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol Unclear Unclear [2]
MR013583 EGC 1-(3',5'-dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol Unclear Unclear [2]
MR013588 EGC 4'-Deoxy EGC Unclear Unclear [2]
MR013586 GA Pyrogallol Unclear Unclear [2]
MR013561 1-(3',4',5'-trihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol 4-hydroxy-5-(3',4',5'-trihydroxyphenyl)valeric acid Unclear Unclear [2]
MR013578 1-(3',4',5'-trihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol 1-(3',5'-dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol Unclear Unclear [2]
MR013978 1-(3',5'-dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol 4-hydroxy-5-(3',5'-dihydroxyphenyl)valeric acid Unclear Unclear [2]
MR013587 Pyrogallol Catechol Unclear Unclear [2]
MR013579 1-(3',5'-dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol 4-hydroxy-5-(3',5'-dihydroxyphenyl)valeric acid Unclear Unclear [2]
MR013562 4-hydroxy-5-(3',4',5'-trihydroxyphenyl)valeric acid 5-(3',4',5'-trihydroxyphenyl)--valerolactone Unclear Unclear [2]
MR013573 4-hydroxy-5-(3',4',5'-trihydroxyphenyl)valeric acid 5-(3',4',5'-trihydroxyphenyl)valeric acid Unclear Unclear [2]
MR013979 4-hydroxy-5-(3',5'-dihydroxyphenyl)valeric acid 5-(3',5'-dihydroxyphenyl)--valerolactone Unclear Unclear [2]
MR013982 4-hydroxy-5-(3',5'-dihydroxyphenyl)valeric acid 3-(3',5'-dihydroxyphenyl)propionic acid Unclear Unclear [2]
MR013580 4-hydroxy-5-(3',5'-dihydroxyphenyl)valeric acid 5-(3',5'-dihydroxyphenyl)--valerolactone Unclear Unclear [2]
MR013584 4-hydroxy-5-(3',5'-dihydroxyphenyl)valeric acid 3-(3',5'-dihydroxyphenyl)propionic acid Unclear Unclear [2]
MR013563 5-(3',4',5'-trihydroxyphenyl)--valerolactone 5-(3',4'-dihydroxyphenyl)--valerolactone Unclear Unclear [2]
MR013570 5-(3',4',5'-trihydroxyphenyl)--valerolactone 5-(3',5'-dihydroxyphenyl)--valerolactone Unclear Unclear [2]
MR013574 5-(3',4',5'-trihydroxyphenyl)valeric acid 4'-hydroxyphenylacetic acid Unclear Unclear [2]
MR013980 5-(3',5'-dihydroxyphenyl)--valerolactone 5-(3',5'-dihydroxyphenyl)valeric acid Unclear Unclear [2]
MR013575 4'-hydroxyphenylacetic acid 3',4'-dihydroxyphenylacetic acid Unclear Unclear [2]
MR013576 4'-hydroxyphenylacetic acid 4'-hydroxybenzoic acid Unclear Unclear [2]
MR013582 4'-hydroxyphenylacetic acid 3-methoxy-4'-hydroxyphenlacetic acid Unclear Unclear [2]
MR013564 5-(3',4'-dihydroxyphenyl)--valerolactone 5-(3',4'-dihydroxyphenyl)-propionic acid Unclear Unclear [2]
MR013571 5-(3',5'-dihydroxyphenyl)--valerolactone 5-(3',5'-dihydroxyphenyl)valeric acid Unclear Unclear [2]
MR013581 5-(3',5'-dihydroxyphenyl)--valerolactone Epigallocatechin gallate Metabolite 14 Unclear Unclear [4]
MR013981 5-(3',5'-dihydroxyphenyl)valeric acid 5-(3'-hydroxyphenyl)valeric acid Unclear Unclear [2]
MR013973 3',4'-dihydroxyphenylacetic acid 3'-hydroxyphenylacetic acid Unclear Unclear [2]
MR013974 3',4'-dihydroxyphenylacetic acid 3'-hydroxybenzoic acid Unclear Unclear [2]
MR013577 4'-hydroxybenzoic acid Hippuric acid Unclear Unclear [2]
MR013565 5-(3',4'-dihydroxyphenyl)-propionic acid 3',4'-dihydroxyphenylacetic acid Unclear Unclear [2]
MR013568 5-(3',4'-dihydroxyphenyl)-propionic acid 3-(3'-hydroxyphenyl)-propionic acid Unclear Unclear [2]
MR013569 5-(3',4'-dihydroxyphenyl)-propionic acid 3-(4'-hydroxyphenyl)-propionic acid Unclear Unclear [2]
MR013572 5-(3',5'-dihydroxyphenyl)valeric acid 5-(3'-hydroxyphenyl)valeric acid Unclear Unclear [2]
MR013566 3',4'-dihydroxyphenylacetic acid 3'-hydroxyphenylacetic acid Unclear Unclear [2]
MR013567 3',4'-dihydroxyphenylacetic acid 3'-hydroxybenzoic acid Unclear Unclear [2]
⏷ Show the Full List of 38 MR(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7002).
2 Absorption, metabolism, bioactivity, and biotransformation of epigallocatechin gallate
3 4-Sulfation Is the Major Metabolic Pathway of Epigallocatechin-3-gallate in Humans: Characterization of Metabolites, Enzymatic Analysis, and Pharmacokinetic Profiling
4 Absorption, metabolism, anti-cancer effect and molecular targets of epigallocatechin gallate (EGCG): An updated review

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