cis-Caftaric acid (CHEM026401)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:58:00 UTC
Update Date2016-11-09 01:18:16 UTC
Accession NumberCHEM026401
Identification
Common Namecis-Caftaric acid
ClassSmall Molecule
DescriptionA cinnamate ester obtained by formal condensation of the carboxy group of cis-caffeic acid with one of the hydroxy groups of meso-tartaric acid.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,3R)-cis-Caffeoyl tartaric acidChEBI
cis-Caftaric acidChEBI
(2S,3R)-cis-Caffeoyl tartarateGenerator
cis-CaftarateGenerator
(2S,3R)-cis-CaftarateGenerator
Chemical FormulaC13H12O9
Average Molecular Mass312.230 g/mol
Monoisotopic Mass312.048 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
Traditional Name(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
SMILES[H]\C(=C(/[H])C1=CC(O)=C(O)C=C1)C(=O)O[C@]([H])(C(O)=O)[C@@]([H])(O)C(O)=O
InChI IdentifierInChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2-/t10-,11+/m1/s1
InChI KeySWGKAHCIOQPKFW-ADAMHKFESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Tricarboxylic acid or derivatives
  • Styrene
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Sugar acid
  • Fatty acid ester
  • Phenol
  • Beta-hydroxy acid
  • Fatty acyl
  • Benzenoid
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP1.68ALOGPS
logP0.6ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area161.59 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity69.74 m³·mol⁻¹ChemAxon
Polarizability27.4 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0973000000-1a96d8a708695d13762eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gr-2940000000-a24c1bc2573e378ccd7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0540-4900000000-55b90a17ab1875f9bb88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0409-3982000000-aabe941096f73c4a6cd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02dr-3940000000-9757ec14c725e63e898eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03mi-3910000000-aec72816b3809d559efeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0953000000-73e8456dc90c46f75a48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0910000000-f57e0a85c0c0b23de9d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qi-0900000000-c2b1f17714cf93428742Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-9845000000-8fac8da9308f88f4517fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-4920000000-674af8a072e4e7b09d49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f80-3900000000-a422c010a9d9a7346f8fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0303060
FooDB IDFDB007549
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30785782
ChEBI ID76082
PubChem Compound ID72551521
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available