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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:30:30 UTC
Update Date2019-07-23 06:16:32 UTC
HMDB IDHMDB0034621
Secondary Accession Numbers
  • HMDB34621
Metabolite Identification
Common Name2-O-Acetyl-trans-coutaric acid
Description2-O-Acetyl-trans-coutaric acid belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. 2-O-Acetyl-trans-coutaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-O-Acetyl-trans-coutaric acid has been detected, but not quantified in, green vegetables. This could make 2-O-acetyl-trans-coutaric acid a potential biomarker for the consumption of these foods.
Structure
Data?1563862592
Synonyms
ValueSource
2-O-Acetyl-trans-coutarateGenerator
2-O-Acetyl-3-trans-O-p-coumaroyltartaric acidHMDB
2-(Acetyloxy)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioateGenerator
Chemical FormulaC15H14O9
Average Molecular Weight338.2663
Monoisotopic Molecular Weight338.063782046
IUPAC Name2-(acetyloxy)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
Traditional Name2-(acetyloxy)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
CAS Registry Number106928-35-2
SMILES
CC(=O)OC(C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C15H14O9/c1-8(16)23-12(14(19)20)13(15(21)22)24-11(18)7-4-9-2-5-10(17)6-3-9/h2-7,12-13,17H,1H3,(H,19,20)(H,21,22)/b7-4+
InChI KeyAILCSCQIQZTQJR-QPJJXVBHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acid esters
Alternative Parents
Substituents
  • Coumaric acid ester
  • Tetracarboxylic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Sugar acid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point194 - 198 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP1.94ALOGPS
logP1.34ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area147.43 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity76.91 m³·mol⁻¹ChemAxon
Polarizability31.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-4910000000-b49ffe2cf366fa81ae95Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01bl-9360330000-de8dc951995157a09450Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-009b-1946000000-a96cb96a8f5c391c5d58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0921000000-61429a01d06f041f657eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-2900000000-8a4e68251c193b7a6bd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06rg-4972000000-13326cd7eaa2968bb9bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-4930000000-6c1d2cf284fa9bd05f7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-8910000000-c25646efb0d6dc657b12Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013140
KNApSAcK IDNot Available
Chemspider ID8557914
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10382471
PDB IDNot Available
ChEBI ID140766
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .