Homovanillic acid (CHEM003297)

Record Information
Version1.0
Creation Date2014-08-29 06:29:15 UTC
Update Date2026-05-21 14:38:36 UTC
Accession NumberCHEM003297
Identification
Common NameHomovanillic acid
ClassSmall Molecule
Description
Homovanillic acid is a dopamine metabolite occurring in human biofluids. A high proportion of patients with neuroblastoma excrete increased amounts of it in their urine. Homovanillic acid is a major catecholamine metabolite. It is used as a reagent to detect oxidative enzymes.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Ether
  • Food Toxin
  • Indicator and Reagent
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
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 Mass182.173 g/mol
Monoisotopic Mass182.058 g/mol
CAS Registry Number306-08-1
IUPAC Name2-(4-hydroxy-3-methoxyphenyl)acetic acid
Traditional Namehomovanillic acid
SMILESCOC1=CC(CC(O)=O)=CC=C1O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Brain
  • Caudate Nucleus
  • Central Nervous System
  • Fibroblasts
  • Kidney
  • Spinal Cord
  • Striatum
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006 map00350
Dopamine beta-hydroxylase deficiencySMP00498 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point138 - 140°C
Boiling PointNot Available
Solubility17 mg/mL
Predicted Properties
PropertyValueSource
Water Solubility2.72 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0000118
FooDB IDFDB001783
Phenol Explorer ID574
KNApSAcK IDC00029504
BiGG ID46066
BioCyc IDCPD-7651
METLIN ID971
PDB IDNot Available
Wikipedia LinkHomovanillic_acid
Chemspider ID1675
ChEBI ID545959
PubChem Compound ID1738
Kegg Compound IDC05582
YMDB IDYMDB01711
ECMDB IDM2MDB005324
References
Synthesis ReferenceNot Available
MSDSLink
General References
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