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Record Information
Version5.0
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 within olives. This could make homoveratric acid a potential biomarker for the consumption of these foods. A phenylacetic acid substituted at positions 3 and 4 by methoxy groups.
Structure
Data?1582752131
Synonyms
ValueSource
2-(3,4-Dimethoxyphenyl)acetic acidChEBI
2-(3,4-Dimethoxyphenyl)ethanoic acidChEBI
3,4-Dimethoxybenzeneacetic acidChEBI
3,4-Dimethoxyphenylacetic acidChEBI
Homoveratrumic acidChEBI
2-(3,4-Dimethoxyphenyl)acetateGenerator
2-(3,4-Dimethoxyphenyl)ethanoateGenerator
3,4-DimethoxybenzeneacetateGenerator
3,4-DimethoxyphenylacetateGenerator
HomoveratrumateGenerator
HomoveratrateGenerator
(3,4-Dimethoxyphenyl)acetateHMDB
(3,4-Dimethoxyphenyl)acetic acidHMDB
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 Molecular Properties
PropertyValueReference
Melting Point96 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available145.42731661259
DarkChem[M-H]-PredictedNot Available145.41931661259
AllCCS[M+H]+PredictedNot Available143.06832859911
AllCCS[M-H]-PredictedNot Available142.94432859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Homoveratric acid,1TMS,#11730.9667https://arxiv.org/abs/1905.12712
Homoveratric acid,1TBDMS,#11955.5126https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-b8fad1a07cec70a67baa2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zmm-8900000000-293e74b0bdba71f586862017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-b8fad1a07cec70a67baa2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zmm-8900000000-293e74b0bdba71f586862018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0900000000-b5afe425cd0ee57b8a782017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-9740000000-e742775074430d01470b2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-2a12c40170fec46f4a142012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-0900000000-5debb25eef3cd12b8c672012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00dl-9800000000-dcdcc653f9617b708e092012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-b8fad1a07cec70a67baa2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-006x-9700000000-f934c6c85d66ecf9a73f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-7921f2d592d19e47e26f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-8900000000-2dc71b5f18fc3e44e4012021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-861708737c6c00d8f8892021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-6341a3b972b9136bfab02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-cfa658289cf1b2ad7c0f2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-d63fee5bd99fb0c1bef22017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-4d0e7df1745cd9e8f8622017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uds-4900000000-03114ec385c930dff86c2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0900000000-ef409f5435da30dee6422017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0900000000-b30d032851ea7f9114312017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059j-3900000000-fc353d8a9dee7319f9002017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-1b5f2103af53001771c32021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbi-7900000000-1b3c176380ec60fbf5ca2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-4900000000-1d4b6f821ff70bd6ff972021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
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 QuantifiedNot QuantifiedAdult (>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 ID86655
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB 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 ]