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Showing Compound 2-O-p-Coumaroylhydroxycitric acid (FDB020348)

Record Information
Version1.0
Creation date2010-04-08 22:14:58 UTC
Update date2019-11-26 03:18:48 UTC
Primary IDFDB020348
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-O-p-Coumaroylhydroxycitric acid
Description2-O-p-Coumaroylhydroxycitric 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-p-Coumaroylhydroxycitric acid has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, corns (Zea mays), and fats and oils. This could make 2-O-p-coumaroylhydroxycitric acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-O-p-Coumaroylhydroxycitric acid.
CAS Number62345-85-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.17 g/LALOGPS
logP0.91ALOGPS
logP0.69ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.04ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area178.66 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity78.51 m³·mol⁻¹ChemAxon
Polarizability31.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H14O10
IUPAC name2-hydroxy-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid
InChI IdentifierInChI=1S/C15H14O10/c16-9-4-1-8(2-5-9)3-6-11(19)25-12(13(20)21)15(24,14(22)23)7-10(17)18/h1-6,12,16,24H,7H2,(H,17,18)(H,20,21)(H,22,23)/b6-3+
InChI KeyZHUVVSHTKJAVQB-ZZXKWVIFSA-N
Isomeric SMILESOC(=O)CC(O)(C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O)C(O)=O
Average Molecular Weight354.2657
Monoisotopic Molecular Weight354.058696668
Classification
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
  • Tetracarboxylic acid or derivatives
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Styrene
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty acyl
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Monosaccharide
  • Hydroxy acid
  • Benzenoid
  • Tertiary alcohol
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • 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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-O-p-Coumaroylhydroxycitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-3901000000-01c91a9b2f6654c55566Spectrum
Predicted GC-MS2-O-p-Coumaroylhydroxycitric acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014l-5191021000-98f7c271502d0498e74cSpectrum
Predicted GC-MS2-O-p-Coumaroylhydroxycitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-O-p-Coumaroylhydroxycitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052v-0549000000-b6d51736d0371fc052522017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-7952000000-d04ed258aac03d606bb32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-2900000000-9173f6449fdb0d2f01292017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05o0-2965000000-fd079dd3e6401c3719b52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5i-6793000000-87f9c6be007aead4c6792017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tk-6930000000-beccf4c5b9887211f3d72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0296-0090000000-158b1ec63bdc9e4745ba2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1940000000-7fd50dd66bba2e81fe442021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9400000000-3629dd807d6e2501d8252021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4u-1119000000-762d4e76facc692cda902021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-2930000000-0d4f931e4b5ffa005a7a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-8900000000-16d9bb8a0cde5be7de932021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40570
CRC / DFC (Dictionary of Food Compounds) IDCSH81-X:MPP70-S
EAFUS IDNot Available
Dr. Duke ID2-O-P-COUMAROYL-HYDROXY-CITRIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).