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

General Information of Drug (ID: DR0012)
Drug Name
Benzotetronic acid
Synonyms
Coumarin, 4-hydroxy-; X954ZLL2RD; 1076-38-6; 2-Hydroxychromone; 2-hydroxychromen-4-one; 2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-; 4-Coumarinol; 4-Hydroxycoumarin; 4-HYDROXY-1-BENZOPYRAN-2-ONE; 4-Hydroxy-2H-1-benzopyran-2-one; 4-Hydroxy-2H-chromen-2-one; 4-Hydroxy-chromen-2-one; 4-Hydroxycoumarin, 98%; 4-Hydroxycoumarine; 4-hydroxy-2-chromenone; 4-hydroxy-coumarin; 4-hydroxychromen-2-one; 4H-1-Benzopyran-4-one, 2-hydroxy-; AI3-52393; BRN 0129768; CHEMBL301141; EINECS 214-060-2; MFCD00006856; NSC 11889; UNII-X954ZLL2RD
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 162.14 Topological Polar Surface Area 46.5
Heavy Atom Count 12 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
54682930
ChEBI ID
CHEBI:40070
CAS Number
1076-38-6
Formula
C9H6O3
Canonical SMILES
C1=CC=C2C(=C1)C(=CC(=O)O2)O
InChI
1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H
InChIKey
VXIXUWQIVKSKSA-UHFFFAOYSA-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
17-noraphidicolinone DM007023 N. A. Unclear 1 [4]
18-noraphidicolinone isomers DM007022 N. A. Unclear 1 [4]
2-Keto DM007030 N. A. Oxidation - Oxidationn 1 [2]
3-ketoaphidicolin DM007021
21670947
Unclear 1 [4]
Cis-Diol DM007032
20136470
Oxidation - Hydrolyzationn 1 [2]
RS-8359 Glucuronide DM007033 N. A. Conjugation - Glucuronidation 1 [2]
Trans-Diol DM007034 N. A. Oxidation - Hydrolyzationn 1 [2]
2-Keto-ci8-dlol DM007031 N. A. Oxidation - Oxidationn 2 [2]
2-Keto-ci8-dlol DM007031 N. A. Oxidation - Hydrolyzationn 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007650 Benzotetronic acid 3-ketoaphidicolin Unclear Unclear [4]
MR007651 Benzotetronic acid 18-noraphidicolinone isomers Unclear Unclear [4]
MR007652 Benzotetronic acid 17-noraphidicolinone Unclear Unclear [4]
MR007664 Benzotetronic acid 2-Keto Oxidation - Oxidationn AOX1 [2]
MR007666 Benzotetronic acid Cis-Diol Oxidation - Hydrolyzationn CYP [2]
MR007668 Benzotetronic acid RS-8359 Glucuronide Conjugation - Glucuronidation UGT [2]
MR007669 Benzotetronic acid Trans-Diol Oxidation - Hydrolyzationn CYP [2]
MR007665 2-Keto 2-Keto-ci8-dlol Oxidation - Hydrolyzationn CYP [2]
MR007667 Cis-Diol 2-Keto-ci8-dlol Oxidation - Oxidationn AOX1 [2]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde oxidase (AOX1) DME0052 Homo sapiens
AOXA_HUMAN
1.2.3.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D1074-D1082. (id: DB03410)
2 Stereoselective pharmacokinetics of RS-8359, a selective and reversible MAO-A inhibitor, by species-dependent drug-metabolizing enzymes. Chirality. 2005 Mar;17(3):135-41.
3 CYP3A4 and CYP2A6 activities marked by the metabolism of lignocaine and coumarin in patients with liver and kidney diseases and epileptic patients. Br J Clin Pharmacol. 1995 Jan;39(1):71-6.
4 The mechanism of aphidicolin bioinactivation by rat liver in vitro systems. Xenobiotica. 1990 Mar;20(3):273-87.

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