2-O-Caffeoylhydroxycitric acid (CHEM033741)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:23:41 UTC
Update Date2016-11-09 01:20:59 UTC
Accession NumberCHEM033741
Identification
Common Name2-O-Caffeoylhydroxycitric acid
ClassSmall Molecule
Description2-O-Caffeoylhydroxycitric acid is found in cereals and cereal products. 2-O-Caffeoylhydroxycitric acid is a constituent of Spondias mombin (yellow mombin) and Zea mays (sweet corn).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-O-CaffeoylhydroxycitrateGenerator
1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylateHMDB
Chemical FormulaC15H14O11
Average Molecular Mass370.265 g/mol
Monoisotopic Mass370.054 g/mol
CAS Registry Number62345-87-3
IUPAC Name1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylic acid
Traditional Name1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylic acid
SMILESOC(=O)CC(O)(C(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O)C(O)=O
InChI IdentifierInChI=1S/C15H14O11/c16-8-3-1-7(5-9(8)17)2-4-11(20)26-12(13(21)22)15(25,14(23)24)6-10(18)19/h1-5,12,16-17,25H,6H2,(H,18,19)(H,21,22)(H,23,24)/b4-2+
InChI KeyOUWOVSUGDPWIBY-DUXPYHPUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTetracarboxylic acids and derivatives
Direct ParentTetracarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tetracarboxylic acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • Styrene
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monosaccharide
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Benzenoid
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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 Solubility1.21 g/LALOGPS
logP1.45ALOGPS
logP0.39ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area198.89 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity80.49 m³·mol⁻¹ChemAxon
Polarizability32.65 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3902000000-aec6d915e889089ce3f5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000l-4090010000-abd1e0dbe3ac0970b139Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w90-0419000000-33352a2338cd5789fe16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-7934000000-8d1a14dca1c33aa1dccbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06yn-2900000000-b6ba1d6cee46079acd8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-2839000000-3eb09ec8162d4f9903f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0560-7975000000-31c4cbb6759d79ecb45eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03y0-8940000000-01e1adfba23ef4a6b4b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ir0-0509000000-082978e8be560955b4c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02mr-0970000000-ae5a331e1bf5752cf1adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-3910000000-a637d56718197362ca0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-057i-1094000000-4200505a56a603c7d4a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1920000000-d0e418fbcfffa8a327c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9300000000-5c78faebc298b1bcad9fSpectrum
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 IDHMDB0040572
FooDB IDFDB020350
Phenol Explorer IDNot Available
KNApSAcK IDC00054230
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014965
ChEBI ID169788
PubChem Compound ID24797519
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.