CHEBI:545959 - homovanillic acid

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ChEBI Name homovanillic acid
ChEBI ID CHEBI:545959
Definition A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:5758
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Formula C9H10O4
Net Charge 0
Average Mass 182.17330
Monoisotopic Mass 182.058
InChI 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
SMILES COc1cc(CC(O)=O)ccc1O
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing homovanillic acid (CHEBI:545959) has functional parent (3,4-dihydroxyphenyl)acetic acid (CHEBI:41941)
homovanillic acid (CHEBI:545959) has role human metabolite (CHEBI:77746)
homovanillic acid (CHEBI:545959) has role mouse metabolite (CHEBI:75771)
homovanillic acid (CHEBI:545959) is a guaiacols (CHEBI:134251)
homovanillic acid (CHEBI:545959) is a monocarboxylic acid (CHEBI:25384)
homovanillic acid (CHEBI:545959) is conjugate acid of homovanillate (CHEBI:133744)
Incoming N-octylhomovanillamide (CHEBI:64041) has functional parent homovanillic acid (CHEBI:545959)
homovanillate (CHEBI:133744) is conjugate base of homovanillic acid (CHEBI:545959)
IUPAC Name
2-(4-hydroxy-3-methoxyphenyl)acetic acid
Synonyms Sources
(4-hydroxy-3-methoxyphenyl)acetic acid IUPAC
3-Methoxy-4-hydroxyphenylacetate KEGG COMPOUND
3-Methoxy-4-hydroxyphenylacetic acid ChEBI
4-Hydroxy-3-methoxybenzeneacetic acid ChEBI
Homovanillic acid KEGG COMPOUND
HVA ChemIDplus
Vanillacetic acid ChemIDplus
Database Links Databases
C00029504 KNApSAcK
C05582 KEGG COMPOUND
CPD-7651 MetaCyc
HMDB0000118 HMDB
Homovanillic_acid Wikipedia
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Registry Numbers Types Sources
2213447 Reaxys Registry Number Reaxys
306-08-1 CAS Registry Number KEGG COMPOUND
306-08-1 CAS Registry Number ChemIDplus
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Last Modified
11 May 2017