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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:40 UTC
HMDB IDHMDB00434
Secondary Accession NumbersNone
Metabolite Identification
Common NameHomoveratric acid
DescriptionHomoveratric 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). (PMID 7059639 , 14311254 , 588645 , 10834300 ).
Structure
Thumb
Synonyms
ValueSource
(3,4-Dimethoxyphenyl)acetateHMDB
(3,4-Dimethoxyphenyl)acetic acidHMDB
3,4-DimethoxybenzeneacetateHMDB
3,4-Dimethoxybenzeneacetic acidHMDB
3,4-DimethoxyphenylacetateHMDB
3,4-Dimethoxyphenylacetic acidHMDB
HomoveratrateHMDB
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 KeyInChIKey=WUAXWQRULBZETB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Phenylacetate
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.29 m3·mol-1ChemAxon
Polarizability19.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-2a12c40170fec46f4a14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-0900000000-5debb25eef3cd12b8c67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00dl-9800000000-dcdcc653f9617b708e09View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-b8fad1a07cec70a67baaView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID575
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000317
KNApSAcK IDNot Available
Chemspider ID6872
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00434
Metagene LinkHMDB00434
METLIN ID5423
PubChem Compound7139
PDB IDNot Available
ChEBI 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. [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. [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. [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. [10834300 ]