4-O-Caffeoylshikimic acid (CHEM028107)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:13:33 UTC
Update Date2016-11-09 01:18:36 UTC
Accession NumberCHEM028107
Identification
Common Name4-O-Caffeoylshikimic acid
ClassSmall Molecule
Description4-O-Caffeoylshikimic acid is found in fruits. 4-O-Caffeoylshikimic acid is isolated from unripe dates (Phoenix dactylifera).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-O-CaffeoylshikimateGenerator
4-Caffeoylshikimic acidHMDB
Isodactylifric acidHMDB
Isodattelic acidHMDB
4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylateGenerator
Chemical FormulaC16H16O8
Average Molecular Mass336.293 g/mol
Monoisotopic Mass336.085 g/mol
CAS Registry NumberNot Available
IUPAC Name4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylic acid
Traditional Name4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylic acid
SMILESOC1CC(=CC(O)C1OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O
InChI IdentifierInChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(21)24-15-12(19)6-9(16(22)23)7-13(15)20/h1-6,12-13,15,17-20H,7H2,(H,22,23)/b4-2-
InChI KeyVTURJKQJEXSKNY-RQOWECAXSA-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
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Cyclitol or derivatives
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • 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 g/LALOGPS
logP1.21ALOGPS
logP0.79ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.49 m³·mol⁻¹ChemAxon
Polarizability31.94 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-2900000000-ddbdfd437f9b52736d92Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-053r-1025009000-c097cad4212ed7c56ed5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-029i-0927000000-f288268a8b334f3619daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-0911000000-33b0fbb06ba51cdadcbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08i0-1900000000-f57cf67e85173e164e70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0849000000-eee1df17386402b70ffcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0200-0910000000-36ded37edc5e5d6dac2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-1900000000-d61cafa530f1628f0271Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0009000000-69f0543446efaf00ee46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-029i-0936000000-db5f7c95f26c5d2cb5d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1900000000-da7a05aa61b358415bdfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ri-0469000000-b402f80e88a2e14cc7dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0943000000-b1e81b5da4335a2801b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-1920000000-f83c49daaca61b7eb338Spectrum
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 IDHMDB0033997
FooDB IDFDB012231
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013684
ChEBI IDNot Available
PubChem Compound ID131751510
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.