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

General Information of Drug (ID: DR0386)
Drug Name
Coumarin
Synonyms
Benzo-a-pyrone; Benzo-alpha-pyrone; Coumarine; Coumarinic anhydride; Coumarinic lactone; Kumarin; Kumarin [Czech]; Rattex; Tonka bean camphor; chromen-2-one; cis-o-Coumarinic acid lactone; coumarin; cumarin; o-Coumaric acid lactone; o-Hydroxycinnamic acid lactone; o-Hydroxycinnamic lactone; 1,2-Benzopyrone; 1-Benzopyran-2-one; 2-Oxo-1,2-benzopyran; 2H-1-Benzopyran, 2-oxo-; 2H-1-Benzopyran-2-one; 2H-Benzo(b)pyran-2-one; 2H-Benzo[b]pyran-2-one; 2H-Chromen-2-one; 5,6-Benzo-2-pyrone; 5,6-Benzo-alpha-pyrone; 91-64-5; Caswell No. 259C
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 146.14 Topological Polar Surface Area 26.3
Heavy Atom Count 11 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
323
ChEBI ID
CHEBI:28794
CAS Number
91-64-5
TTD Drug ID
D03ZMQ
Formula
C9H6O2
Canonical SMILES
CC(=C)C(C(C1=C(C=C2C(=C1)C=CC(=O)O2)OC)O)O
InChI
1S/C15H16O5/c1-8(2)14(17)15(18)10-6-9-4-5-13(16)20-11(9)7-12(10)19-3/h4-7,14-15,17-18H,1H2,2-3H3
InChIKey
ZYGHJZDHTFUPRJ-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
3-Hydroxycoumarin DM004920
13650
Oxidation - Aromatic hydroxylation 1 [4]
4-Hydroxycoumarin DM004921
54682930
Oxidation - Hydrolyzationn 1 [7]
5-Hydroxycoumarin DM004922
5318179
Oxidation - Hydrolyzationn 1 [7]
6-Hydroxycoumarin DM004923
99477
Oxidation - Hydrolyzationn 1 [7]
7-Hydroxycoumarin DM004919
5281426
Oxidation - Hydroxy Aromaticlation 1 [4] , [5]
8-Hydroxycoumarin DM004924
122783
Oxidation - Hydrolyzationn 1 [7]
Coumarin 3,4-epoxide DM004916
126771
Oxidation - Epoxidation 1 [4]
O-Hydroxyphenyl-propionic Acid DM004926
873
Unclear 1 [7]
O-Hydroxyphenylethanol DM004925
82200
Unclear 1 [4]
O-Hydroxyphenyl-acetaldehyde DM004917 N. A. Unclear 2 [4]
O-Hydroxyphenyl-acetic Acid DM004918
11970
Unclear 3 [4]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005306 Coumarin Coumarin 3,4-epoxide Oxidation - Epoxidation CYP1A1 ... [4]
MR005309 Coumarin 7-Hydroxycoumarin Oxidation - Hydroxy Aromaticlation CYP1A1 ... [4], [5]
MR005310 Coumarin 3-Hydroxycoumarin Oxidation - Aromatic hydroxylation CYP3A4 [4]
MR005311 Coumarin 4-Hydroxycoumarin Oxidation - Hydrolyzationn CYP2A6 [7]
MR005312 Coumarin 5-Hydroxycoumarin Oxidation - Hydrolyzationn CYP2A6 [7]
MR005313 Coumarin 6-Hydroxycoumarin Oxidation - Hydrolyzationn CYP2A6 [7]
MR005314 Coumarin 8-Hydroxycoumarin Oxidation - Hydrolyzationn CYP2A6 [7]
MR005315 Coumarin O-Hydroxyphenylethanol Unclear Unclear [4]
MR005316 Coumarin O-Hydroxyphenyl-propionic Acid Unclear Unclear [7]
MR005307 Coumarin 3,4-epoxide O-Hydroxyphenyl-acetaldehyde Unclear Unclear [4]
MR005308 O-Hydroxyphenyl-acetaldehyde O-Hydroxyphenyl-acetic Acid Unclear Unclear [4]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 102D1 (cyp102) DME1465 Streptomyces avermitilis
CPXB_BACMB
1.14.14.1
[2] , [3]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[4]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[4] , [5]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[4] , [5]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[6]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
⏷ Show the Full List of 8  DME(s)
References
1 Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem. 2010 Jan 14;53(1):335-44.
2 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
3 Cloning, expression and characterization of CYP102D1, a self-sufficient P450 monooxygenase from Streptomyces avermitilis. FEBS J. 2012 May;279(9):1650-62.
4 Identification of the cytochromes P450 that catalyze coumarin 3,4-epoxidation and 3-hydroxylation
5 Species differences and interindividual variation in liver microsomal cytochrome P450 2A enzymes: effects on coumarin, dicumarol, and testosterone oxidation
6 Pharmacogenomics of CYP2C9: functional and clinical considerations. J Pers Med. 2017 Dec 28;8(1).
7 Coumarin metabolism by rat esophageal microsomes and cytochrome P450 2A3

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