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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-05-23 20:47:48 UTC
HMDB IDHMDB0000333
Secondary Accession Numbers
  • HMDB00333
Metabolite Identification
Common NameIsohomovanillic acid
DescriptionIsohomovanillic acid is a deaminated metabolite of catecholamines formed by the enzyme catechol-O-methyltransferase (COMT; EC 2.1.1.6) which catalyzes the transfer of a methyl group from S-adenosylmethionine to catecholamines, including the neurotransmitters dopamine, epinephrine, and norepinephrine. This O-methylation results in one of the major degradative pathways of the catecholamine transmitters. (OMIM 116790 ).
Structure
Data?1558644468
Synonyms
ValueSource
Homoisovanillic acidChEBI
HomoisovanillateGenerator
IsohomovanillateGenerator
3-Hydroxy-4-methoxyphenylacetateHMDB
3-Hydroxy-4-methoxyphenylacetic acidHMDB
4-Methoxy-3-hydroxyphenylacetateHMDB
4-Methoxy-3-hydroxyphenylacetic acidHMDB
Homo-iso-vanillic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-(3-hydroxy-4-methoxyphenyl)acetic acid
Traditional Nameisohomovanillic acid
CAS Registry Number1131-94-8
SMILES
COC1=CC=C(CC(O)=O)C=C1O
InChI Identifier
InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)
InChI KeyBWXLCOBSWMQCGP-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-4-unsubstituted benzenoid
  • 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
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.64 g/LALOGPS
logP0.88ALOGPS
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
Polarizability17.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2900000000-4e352872bb3470aa8136JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01w0-9352000000-143f546e1228ddc2e715JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-91acb75622a4c8f430d5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-a125f1e015a1c73b12eeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-9800000000-f5d1b07059db50410c4fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0900000000-ef1cc468bfa35cfd42d9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-0900000000-4db0068faa2042576868JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-6900000000-023c60c5b54990926d1cJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Not SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Not SpecifiedNot Specified
Parkinson's Disease
details
Associated Disorders and Diseases
Disease References
Parkinson's disease
  1. Ebinger G, Adriaenssens K: Iso-homovanillic acid determination in cerebrospinal fluid and in urine during L-DOPA treatment of Parkinson's disease. Clin Chim Acta. 1973 Nov 15;48(4):427-31. [PubMed:4761590 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021958
KNApSAcK IDNot Available
Chemspider ID141092
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5322
PubChem Compound160562
PDB IDNot Available
ChEBI ID70818
References
Synthesis ReferenceHarlay, Victor. Synthesis of homoisovanillic acid. New method for the preparation of homoveratric acid. Compt. rend. (1946), 223 675-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Muskiet FA, Fremouw-Ottevangers DC, Nagel GT, Wolthers BG: Determination of 4-O-methylated catecholamine metabolites in urine by mass fragmentography. Clin Chem. 1979 Oct;25(10):1708-13. [PubMed:476919 ]

Enzymes

General function:
Involved in magnesium ion binding
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.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77