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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:11 UTC
HMDB IDHMDB0000434
Secondary Accession Numbers
  • HMDB00434
Metabolite Identification
Common NameHomoveratric acid
DescriptionHomoveratric acid, also known as homoveratrate, belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. Homoveratric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, homoveratric acid is found, on average, in the highest concentration in olives. homoveratric acid has also been detected, but not quantified in, . This could make homoveratric acid a potential biomarker for the consumption of these foods. Homoveratric acid is the main metabolite of 3,4-dimethoxyphenylethylamine (DMPEA) in urine. It has been suggested that DMPEA and other amines are in higher concentrations in drug-free schizophrenics than in normal subjects. DMPEA is a the di-methylated metabolite of L-DOPA, the major treatment for Parkinson's disease (PD).
Structure
Data?1582752131
Synonyms
ValueSource
HomoveratrateGenerator
(3,4-Dimethoxyphenyl)acetateHMDB
(3,4-Dimethoxyphenyl)acetic acidHMDB
3,4-DimethoxybenzeneacetateHMDB
3,4-Dimethoxybenzeneacetic acidHMDB
3,4-DimethoxyphenylacetateHMDB
3,4-Dimethoxyphenylacetic acidHMDB
2-(3,4-Dimethoxyphenyl)acetateHMDB
Chemical FormulaC10H12O4
Average Molecular Weight196.1999
Monoisotopic Molecular Weight196.073558872
IUPAC Name2-(3,4-dimethoxyphenyl)acetic acid
Traditional Name3,4-dimethoxyphenylacetic acid
CAS Registry Number93-40-3
SMILES
COC1=CC=C(CC(O)=O)C=C1OC
InChI Identifier
InChI=1S/C10H12O4/c1-13-8-4-3-7(6-10(11)12)5-9(8)14-2/h3-5H,6H2,1-2H3,(H,11,12)
InChI KeyWUAXWQRULBZETB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point96 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP1.58ALOGPS
logP1.3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.86ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.29 m³·mol⁻¹ChemAxon
Polarizability19.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-b8fad1a07cec70a67baaSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zmm-8900000000-293e74b0bdba71f58686Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-b8fad1a07cec70a67baaSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zmm-8900000000-293e74b0bdba71f58686Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0900000000-b5afe425cd0ee57b8a78Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-9740000000-e742775074430d01470bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-2a12c40170fec46f4a14Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-0900000000-5debb25eef3cd12b8c67Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00dl-9800000000-dcdcc653f9617b708e09Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-b8fad1a07cec70a67baaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-d63fee5bd99fb0c1bef2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-4d0e7df1745cd9e8f862Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uds-4900000000-03114ec385c930dff86cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0900000000-ef409f5435da30dee642Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0900000000-b30d032851ea7f911431Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059j-3900000000-fc353d8a9dee7319f900Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.687 +/- 0.175 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.5 +/- 0.155 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.691 +/- 0.164 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.908 +/- 0.314 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.645 +/- 0.129 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.904 +/- 0.193 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.594 +/- 0.174 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.613 +/- 2.137 uMAdult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
UrineDetected and Quantified0.072 +/- 0.01 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID575
FooDB IDFDB000317
KNApSAcK IDNot Available
Chemspider ID6872
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5423
PubChem Compound7139
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceAboulezz, A. F.; Quelet, R. Derivatives of veratrole. Synthesis of homoveratric acid and some substituted diphenylmethane and fluorenone derivatives. Journal of Chemistry of the United Arab Republic (1962), 5(2), 137-46.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hempel K, Ullrich H, Philippu G: Quantitative investigation on the urinary excretion and metabolism of 3,4-dimethoxyphenylethylamine in schizophrenics and normal individuals. Biol Psychiatry. 1982 Jan;17(1):49-59. [PubMed:7059639 ]
  2. PROENCA J, WENNER J: [ON THE EFFECT OF NIKETHAMIDE AND HOMOVERATRIC ACID DIMETHYLAMIDE ON RESPIRATION IN INFANTS]. Monatsschr Kinderheilkd. 1965 Apr;113:341-3. [PubMed:14311254 ]
  3. Friedhoff AJ, Park S, Schweitzer JW, Burdock EI, Armour M: Excretion of 3,4-dimethoxyphenethylamine (DMPEA) by acute schizophrenics and controls. Biol Psychiatry. 1977 Oct;12(5):643-54. [PubMed:588645 ]
  4. Charlton CG, Crowell B Jr: Effects of dopamine metabolites on locomotor activities and on the binding of dopamine: relevance to the side effects of L-dopa. Life Sci. 2000 Apr 21;66(22):2159-71. [PubMed:10834300 ]