Showing metabocard for Homovanillic acid (BMDB0000118)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:19:45 UTC
Update Date2020-05-21 16:27:05 UTC
BMDB IDBMDB0000118
Secondary Accession Numbers
  • BMDB00118
Metabolite Identification
Common NameHomovanillic acid
DescriptionHomovanillic acid, also known as vanillacetate or homovanillate, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Homovanillic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Homovanillic acid exists in all living species, ranging from bacteria to humans. Homovanillic acid participates in a number of enzymatic reactions, within cattle. In particular, Homovanillic acid can be biosynthesized from homovanillin; which is catalyzed by the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, Homovanillic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxybenzeneacetic acid and guaiacol through its interaction with the enzyme catechol O-methyltransferase. In cattle, homovanillic acid is involved in the metabolic pathway called the tyrosine metabolism pathway. Homovanillic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4-Hydroxy-3-methoxyphenyl)acetic acidChEBI
3-Methoxy-4-hydroxyphenylacetateChEBI
3-Methoxy-4-hydroxyphenylacetic acidChEBI
4-Hydroxy-3-methoxybenzeneacetic acidChEBI
HVAChEBI
Vanillacetic acidChEBI
(4-Hydroxy-3-methoxyphenyl)acetateGenerator
4-Hydroxy-3-methoxybenzeneacetateGenerator
VanillacetateGenerator
HomovanillateGenerator
3-Methoxy-4-hydroxy-phenylacetic acidHMDB
4-Hydroxy 3-methoxyphenylacetic acidHMDB
4-Hydroxy-3-methoxyphenylacetic acidHMDB
HomovanilateHMDB
Homovanilic acidHMDB
Homovanillinic acidHMDB
VanilacetateHMDB
Vanilacetic acidHMDB
3 Methoxy 4 hydroxyphenylacetic acidHMDB
Acid, 3-methoxy-4-hydroxyphenylaceticHMDB
Acid, 4-hydroxy-3-methoxyphenylaceticHMDB
4 Hydroxy 3 methoxyphenylacetic acidHMDB
Acid, homovanillicHMDB
3'-Methoxy-4'-hydroxyphenylacetic acidHMDB
3’-methoxy-4’-hydroxyphenylacetic acidHMDB
4'-Hydroxy-3'-methoxy-phenylacetic acidHMDB
2-(4-Hydroxy-3-methoxyphenyl)acetic acidHMDB
4'-Hydroxy-3'-methoxyphenylacetic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-(4-hydroxy-3-methoxyphenyl)acetic acid
Traditional Namehomovanillic acid
CAS Registry Number306-08-1
SMILES
COC1=CC(CC(O)=O)=CC=C1O
InChI Identifier
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)
InChI KeyQRMZSPFSDQBLIX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point138 - 140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility17 mg/mLNot Available
LogP0.33LAHANN,TR ET AL. (1989)
Predicted Properties
PropertyValueSource
logP1.02ALOGPS
logP1.15ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.81 m³·mol⁻¹ChemAxon
Polarizability17.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Brain
  • Fibroblasts
  • Kidney
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000118
DrugBank IDNot Available
Phenol Explorer Compound ID574
FooDB IDFDB001783
KNApSAcK IDC00029504
Chemspider ID1675
KEGG Compound IDC05582
BioCyc IDCPD-7651
BiGG ID46066
Wikipedia LinkHomovanillic_acid
METLIN ID971
PubChem Compound1738
PDB IDNot Available
ChEBI ID545959
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in catechol O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol (By similarity).
Gene Name:
COMT
Uniprot ID:
A7MBI7
Molecular weight:
30485.0
Reactions
3,4-Dihydroxybenzeneacetic acid + Guaiacol → Homovanillic acid + Pyrocatecholdetails