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

General Information of Drug (ID: DR2258)
Drug Name
Homovanillic acid
Synonyms
Homovanilic acid; Homovanillate; Homovanillic acid; Homovanillic acid, 98%; Homovanillinic acid; Homovaniuic acid; Vanilacetic acid; Vanillacetic acid; (4-HYDROXY-3-METHOXYPHENYL)ACETIC ACID; 2-(4-hydroxy-3-methoxy-phenyl)acetic acid; 2-(4-hydroxy-3-methoxyphenyl)acetic acid; 3-Methoxy-4-hydroxyphenylacetate; 3-Methoxy-4-hydroxyphenylacetic acid; 306-08-1; 4-Hydroxy-3-methoxybenzeneacetic acid; 4-Hydroxy-3-methoxyphenylacetic acid; Benzeneacetic acid, 4-hydroxy-3-methoxy-; HVA; MFCD00004350; NSC 16682; UNII-X77S6GMS36
Indication Brain cancer [ICD11: 2A00] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 182.17 Topological Polar Surface Area 66.8
Heavy Atom Count 13 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
1738
ChEBI ID
CHEBI:545959
CAS Number
306-08-1
Formula
C9H10O4
Canonical SMILES
COC1=C(C=CC(=C1)CC(=O)O)O
InChI
1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
InChIKey
QRMZSPFSDQBLIX-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
3,6-dihydroxy-2-methoxyphenylacetic acid DM006531 N. A. Oxidation - 1-Hydrolyzationn 1 [3]
Homovanillic acid Metabolite X DM006532 N. A. Reduction - 1,2-dioxygenation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007038 Homovanillic acid 3,6-dihydroxy-2-methoxyphenylacetic acid Oxidation - 1-Hydrolyzationn Unclear [3]
MR007039 3,6-dihydroxy-2-methoxyphenylacetic acid Homovanillic acid Metabolite X Reduction - 1,2-dioxygenation Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Homogentisate 1,2-dioxygenase (hmgA) DME1520 Variovorax paradoxus
A0A0H2M8H5_VARPD
1.13.11.5
[2] , [3]
References
1 Quantification of vanillylmandelic acid, homovanillic acid and 5-hydroxyindoleacetic acid in urine using a dilute-and-shoot and ultra-high pressure liquid chromatography tandem mass spectrometry method. Clin Chem Lab Med. 2018 Aug 28;56(9):1533-1541.
2 Isolation and molecular detection of methylotrophic bacteria occurring in the human mouth. Environ Microbiol. 2005 Aug;7(8):1227-38.
3 Degradation of homovanillate by a strain of Variovorax paradoxus via ring hydroxylation. FEMS Microbiol Lett. 1995 Dec 15;134(2-3):213-9.

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