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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 homoveratrumate, 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 found, on average, in the highest concentration within olives (Olea europaea). Homoveratric acid has also been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make homoveratric acid a potential biomarker for the consumption of these foods. Homoveratric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Homoveratric acid.
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point96 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot 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 Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.42731661259
DarkChem[M-H]-145.41931661259
AllCCS[M+H]+143.06832859911
AllCCS[M-H]-142.94432859911
DeepCCS[M+H]+137.84930932474
DeepCCS[M-H]-135.10130932474
DeepCCS[M-2H]-171.38930932474
DeepCCS[M+Na]+146.92730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Homoveratric acidCOC1=CC=C(CC(O)=O)C=C1OC2934.8Standard polar33892256
Homoveratric acidCOC1=CC=C(CC(O)=O)C=C1OC1641.0Standard non polar33892256
Homoveratric acidCOC1=CC=C(CC(O)=O)C=C1OC1716.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Homoveratric acid,1TMS,isomer #1COC1=CC=C(CC(=O)O[Si](C)(C)C)C=C1OC1731.0Semi standard non polar33892256
Homoveratric acid,1TBDMS,isomer #1COC1=CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=C1OC1955.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Homoveratric acid EI-B (Non-derivatized)splash10-0006-1900000000-b8fad1a07cec70a67baa2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Homoveratric acid EI-B (Non-derivatized)splash10-0zmm-8900000000-293e74b0bdba71f586862017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Homoveratric acid EI-B (Non-derivatized)splash10-0006-1900000000-b8fad1a07cec70a67baa2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Homoveratric acid EI-B (Non-derivatized)splash10-0zmm-8900000000-293e74b0bdba71f586862018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homoveratric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0900000000-b5afe425cd0ee57b8a782017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homoveratric acid GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-9740000000-e742775074430d01470b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homoveratric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homoveratric acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Homoveratric acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-000i-0900000000-2a12c40170fec46f4a142012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homoveratric acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-00di-0900000000-5debb25eef3cd12b8c672012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homoveratric acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-00dl-9800000000-dcdcc653f9617b708e092012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homoveratric acid EI-B (HITACHI M-52) , Positive-QTOFsplash10-0006-1900000000-b8fad1a07cec70a67baa2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homoveratric acid 40V, Negative-QTOFsplash10-006x-9700000000-f934c6c85d66ecf9a73f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homoveratric acid 10V, Negative-QTOFsplash10-000i-0900000000-7921f2d592d19e47e26f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homoveratric acid 40V, Positive-QTOFsplash10-0a6r-8900000000-2dc71b5f18fc3e44e4012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homoveratric acid 20V, Positive-QTOFsplash10-0udi-0900000000-861708737c6c00d8f8892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homoveratric acid 10V, Positive-QTOFsplash10-0udi-0900000000-6341a3b972b9136bfab02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homoveratric acid 20V, Negative-QTOFsplash10-00di-0900000000-cfa658289cf1b2ad7c0f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 10V, Positive-QTOFsplash10-002b-0900000000-d63fee5bd99fb0c1bef22017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 20V, Positive-QTOFsplash10-004j-0900000000-4d0e7df1745cd9e8f8622017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 40V, Positive-QTOFsplash10-0uds-4900000000-03114ec385c930dff86c2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 10V, Negative-QTOFsplash10-0f6t-0900000000-ef409f5435da30dee6422017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 20V, Negative-QTOFsplash10-0f6t-0900000000-b30d032851ea7f9114312017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 40V, Negative-QTOFsplash10-059j-3900000000-fc353d8a9dee7319f9002017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 10V, Positive-QTOFsplash10-0f6t-0900000000-a98871b4ebb2ae3827532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 20V, Positive-QTOFsplash10-0udi-0900000000-94dda491ff4a670ad4a42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 40V, Positive-QTOFsplash10-0f79-4900000000-28d5f869e5bad9c0059f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 10V, Negative-QTOFsplash10-0udi-0900000000-1b5f2103af53001771c32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 20V, Negative-QTOFsplash10-0pbi-7900000000-1b3c176380ec60fbf5ca2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homoveratric acid 40V, Negative-QTOFsplash10-0079-4900000000-1d4b6f821ff70bd6ff972021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView 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
Good Scents 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 ]