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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:37 UTC
Update Date2020-02-26 21:44:24 UTC
HMDB IDHMDB0029783
Secondary Accession Numbers
  • HMDB29783
Metabolite Identification
Common NameMono-trans-p-coumaroylmesotartaric acid
DescriptionMono-trans-p-coumaroylmesotartaric acid belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. Mono-trans-p-coumaroylmesotartaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Mono-trans-p-coumaroylmesotartaric acid has been detected, but not quantified in, a few different foods, such as alcoholic beverages, common grapes, and fruits. This could make mono-trans-p-coumaroylmesotartaric acid a potential biomarker for the consumption of these foods.
Structure
Data?1582753464
Synonyms
ValueSource
mono-trans-p-CoumaroylmesotartarateGenerator
3-Hydroxy-2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}pentanedioateGenerator
trans-p-CoumaroyltartarateGenerator
Chemical FormulaC14H14O8
Average Molecular Weight310.2562
Monoisotopic Molecular Weight310.068867424
IUPAC Name3-hydroxy-2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}pentanedioic acid
Traditional Name3-hydroxy-2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}pentanedioic acid
CAS Registry Number27174-06-7
SMILES
OC(CC(O)=O)C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C14H14O8/c15-9-4-1-8(2-5-9)3-6-12(19)22-13(14(20)21)10(16)7-11(17)18/h1-6,10,13,15-16H,7H2,(H,17,18)(H,20,21)/b6-3+
InChI KeyWZHTXSWUIFRTCQ-ZZXKWVIFSA-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
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Tricarboxylic acid or derivatives
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • Phenol
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Monosaccharide
  • Hydroxy acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • 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 Point198 - 200 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.48 g/LALOGPS
logP1.33ALOGPS
logP0.99ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area141.36 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity72.39 m³·mol⁻¹ChemAxon
Polarizability28.78 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, Positivesplash10-0002-4910000000-40597387784f66f021c9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0159-3491160000-89562b3e70b82d87b1dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01r5-0973000000-3dffa3cd5384b68362b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1930000000-c8093bbd85a8c0b9faa5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002k-4900000000-82cb8369be0ac91d5f1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0cdj-1953000000-f7c38fab93f311056d05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0901-3920000000-683651350f54c250ea97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0292-1900000000-2a4a15cd64597903a29bSpectrum
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 ID470
FooDB IDFDB013138
KNApSAcK IDNot Available
Chemspider ID8284110
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10108584
PDB IDNot Available
ChEBI IDNot Available
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.. .