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Showing Compound cis-Coutaric acid (FDB013139)

Record Information
Version1.0
Creation date2010-04-08 22:10:33 UTC
Update date2019-11-26 03:08:02 UTC
Primary IDFDB013139
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis-Coutaric acid
Descriptioncis-Coutaric acid, also known as cis-coutarate, belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. cis-Coutaric acid is found, on average, in the highest concentration within white wine. cis-Coutaric acid has also been detected, but not quantified in, a few different foods, such as alcoholic beverages, common grapes (Vitis vinifera), and fruits. This could make cis-coutaric acid a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on cis-Coutaric acid.
CAS Number67920-37-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.86 g/LALOGPS
logP1.49ALOGPS
logP0.9ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area141.36 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity67.76 m³·mol⁻¹ChemAxon
Polarizability26.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H12O8
IUPAC name2-hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
InChI IdentifierInChI=1S/C13H12O8/c14-8-4-1-7(2-5-8)3-6-9(15)21-11(13(19)20)10(16)12(17)18/h1-6,10-11,14,16H,(H,17,18)(H,19,20)/b6-3-
InChI KeyINYJZRKTYXTZHP-UTCJRWHESA-N
Isomeric SMILESOC(C(OC(=O)\C=C/C1=CC=C(O)C=C1)C(O)=O)C(O)=O
Average Molecular Weight296.2296
Monoisotopic Molecular Weight296.05321736
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
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Tricarboxylic acid or derivatives
  • Styrene
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Sugar acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Monosaccharide
  • Fatty acyl
  • Benzenoid
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • 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-MScis-Coutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-4910000000-ba96d2f8de6be6c97efeSpectrum
Predicted GC-MScis-Coutaric acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-6491260000-371f03ee0a7d99624a96Spectrum
Predicted GC-MScis-Coutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-2690000000-b5c8d3a07aa9ed38ebf72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ej-3940000000-a1799c7a99ba6feb7dd82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-3910000000-2e0c2fa4d35ecac5a1b12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-9720000000-0a0c84406801b831e0912021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-7900000000-05ba688ac97301129cfc2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-8fc199380ced811553e22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0790000000-783fd770de89781d273d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0032-2950000000-34cbeff6fa8a7110d0ce2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00oa-4900000000-aeb2dc4aefee4b50670d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0940000000-7987f1711c48bb602c0a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0900000000-630089dd29b945a3fb642021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-aa7d4d40daa071395a922021-09-22View 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 ID495
DrugBank IDNot Available
HMDB IDHMDB34620
CRC / DFC (Dictionary of Food Compounds) IDBTJ82-E:HOX88-H
EAFUS IDNot Available
Dr. Duke IDCIS-COUTARIC-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).