Caffeic acid 3-glucoside (CHEM026375)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:57:07 UTC
Update Date2016-11-09 01:18:15 UTC
Accession NumberCHEM026375
Identification
Common NameCaffeic acid 3-glucoside
ClassSmall Molecule
DescriptionA hydroxycinnamic acid that is trans-caffeic acid in which the phenolic hydroxy group at position 3 has been converted into its beta-D-glucoside.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Caffeic acid 3-glucosideChEBI
trans-Caffeic acid 3-O-beta-D-glucosideChEBI
Caffeate 3-glucosideGenerator
trans-Caffeate 3-O-b-D-glucosideGenerator
trans-Caffeate 3-O-beta-D-glucosideGenerator
trans-Caffeate 3-O-β-D-glucosideGenerator
trans-Caffeic acid 3-O-b-D-glucosideGenerator
trans-Caffeic acid 3-O-β-D-glucosideGenerator
3-O-b-D-Glucosyl-trans-caffeateGenerator
3-O-b-D-Glucosyl-trans-caffeic acidGenerator
3-O-beta-D-Glucosyl-trans-caffeateGenerator
3-O-Β-D-glucosyl-trans-caffeateGenerator
3-O-Β-D-glucosyl-trans-caffeic acidGenerator
Chemical FormulaC15H18O9
Average Molecular Mass342.300 g/mol
Monoisotopic Mass342.095 g/mol
CAS Registry NumberNot Available
IUPAC Name(2E)-3-(4-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
Traditional Namecaffeic acid 3-glucoside
SMILES[H]\C(=C(\[H])C1=CC(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)=C(O)C=C1)C(O)=O
InChI IdentifierInChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-5-7(1-3-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+/t10-,12-,13+,14-,15-/m1/s1
InChI KeyQOPSZFXPZWQLOG-VHCZEJTMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hexose monosaccharide
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • O-glycosyl compound
  • Styrene
  • Phenol ether
  • Phenoxy compound
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility6.24 g/LALOGPS
logP-0.61ALOGPS
logP-0.74ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.17 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, Positivesplash10-01sl-0916000000-e677e480f325aeeaf531Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0900000000-1e83f1ba36a7ce61b3aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900000000-748ad099a27ea54d22baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-2928000000-88b5911db1f82a296ebeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1911000000-5f8771b2b4e5a3712d4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01u3-2900000000-614d23c371e61247c801Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901000000-514f52cf631674533b29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0901000000-90fe068e015786922d51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-1910000000-9027d46fe5f0b7b47d34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0409000000-a46e9c18202ca539f626Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0041-0950000000-eb9b37358e2d2872dc9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-0900000000-afb4cbb449fbf6430a6cSpectrum
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 IDHMDB0303040
FooDB IDFDB007443
Phenol Explorer IDNot Available
KNApSAcK IDC00002716
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4445073
ChEBI ID3293
PubChem Compound IDNot Available
Kegg Compound IDC10431
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available