1-O-Caffeoyl-beta-D-glucose (CHEM025637)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:31:17 UTC
Update Date2016-11-09 01:18:07 UTC
Accession NumberCHEM025637
Identification
Common Name1-O-Caffeoyl-beta-D-glucose
ClassSmall Molecule
DescriptionA cinnamate ester obtained by the formal condensation of the 1-hydroxy group of beta-D-glucopyranose with the carboxy group of trans-caffeic acid.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-O-[(e)-Caffeoyl]-beta-D-glucoseChEBI
1-O-[(e)-Caffeoyl]-b-D-glucoseGenerator
1-O-[(e)-Caffeoyl]-β-D-glucoseGenerator
1-Caffeoyl-b-D-glucoseGenerator
1-Caffeoyl-β-D-glucoseGenerator
1-O-(trans-Caffeoyl)-beta-D-glucoseChEBI
1-O-(trans-Caffeoyl)-b-D-glucoseGenerator
1-O-(trans-Caffeoyl)-β-D-glucoseGenerator
1-O-Caffeoyl-b-D-glucoseGenerator
1-O-Caffeoyl-β-D-glucoseGenerator
Chemical FormulaC15H18O9
Average Molecular Mass342.298 g/mol
Monoisotopic Mass342.095 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Name1-caffeoyl-β-D-glucose
SMILESOC[C@H]1O[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(23-10)24-11(19)4-2-7-1-3-8(17)9(18)5-7/h1-5,10,12-18,20-22H,6H2/b4-2+/t10-,12-,13+,14-,15+/m1/s1
InChI KeyWQSDYZZEIBAPIN-VBQORRLJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Stigmastane-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility6.98 g/LALOGPS
logP-0.7ALOGPS
logP-0.51ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.45 m³·mol⁻¹ChemAxon
Polarizability32.44 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0902000000-060c62eea5ffd46733c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-4095e641c6e59bd1ad5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ki-3900000000-2d97576ff9016d49d724Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0902000000-392d992c921bed6395a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-1900000000-b7971434f49fada40a9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fu-7900000000-1ffc1c6b603f8d09f1d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0509000000-9b898e4eff8d99f014e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03l1-1930000000-11d59e94207bd0cf4bbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g0-6900000000-5bf886774fb798c507c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-0905000000-a6a2ed371eeb9966c66cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-3955000000-d99303d226dec38278edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-1900000000-a534c1d60cc6c2e796c6Spectrum
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 IDHMDB0302440
FooDB IDFDB004606
Phenol Explorer IDNot Available
KNApSAcK IDC00002718
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4445075
ChEBI ID614
PubChem Compound ID5281761
Kegg Compound IDC10433
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available