trans-p-Coumaroyl beta-D-glucopyranoside (CHEM024074)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:29:15 UTC
Update Date2016-11-09 01:17:49 UTC
Accession NumberCHEM024074
Identification
Common Nametrans-p-Coumaroyl beta-D-glucopyranoside
ClassSmall Molecule
DescriptionAn O-acyl carbohydrate that is beta-D-glucose bearing a 4-coumaroyl substituent at position 1.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-O-(4-Hydroxycinnamoyl)-beta-D-glucoseChEBI
1-O-(trans-4-Coumaroyl)-beta-D-glucoseChEBI
p-Coumaroyl-beta-D-glucoseChEBI
1-O-(4-Hydroxycinnamoyl)-b-D-glucoseGenerator
1-O-(4-Hydroxycinnamoyl)-β-D-glucoseGenerator
1-O-(trans-4-Coumaroyl)-b-D-glucoseGenerator
1-O-(trans-4-Coumaroyl)-β-D-glucoseGenerator
p-Coumaroyl-b-D-glucoseGenerator
p-Coumaroyl-β-D-glucoseGenerator
1-O-(4-Coumaroyl)-b-D-glucoseGenerator
1-O-(4-Coumaroyl)-β-D-glucoseGenerator
trans-P-Coumaroyl b-D-glucopyranosideGenerator
trans-P-Coumaroyl β-D-glucopyranosideGenerator
1-O-(4-Coumaroyl)-beta-D-glucoseKEGG
Chemical FormulaC15H18O8
Average Molecular Mass326.299 g/mol
Monoisotopic Mass326.100 g/mol
CAS Registry Number13080-39-2
IUPAC Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
Traditional Namep-coumaroyl-D-glucose
SMILESOC[C@H]1O[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(22-10)23-11(18)6-3-8-1-4-9(17)5-2-8/h1-6,10,12-17,19-21H,7H2/b6-3+/t10-,12-,13+,14-,15+/m1/s1
InChI KeyDSNCQKUYZOSARM-QVLXMGEUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acid glycosides
Alternative Parents
Substituents
  • Hydroxycinnamic acid glycoside
  • O-cinnamoyl glycoside
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Hexose monosaccharide
  • Cinnamic acid ester
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Primary alcohol
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Solubility8.2 g/LALOGPS
logP-0.51ALOGPS
logP-0.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.47 m³·mol⁻¹ChemAxon
Polarizability32.26 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-00kb-0902000000-c1d1ff3949ff38aaed4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0900000000-e4a0c0fc809a93114259Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-4900000000-39d845d085a081120f28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0902000000-d505fe911b8d3da07208Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1900000000-38fee86878d2ae9e415eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ow-7900000000-1b0cc7d2e39c0949e024Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0709000000-d41db3a520e3f1ecd785Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1920000000-973b71e0a2cbeb739508Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-6910000000-9a1374eebe7fe5e24442Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02di-0914000000-08c8d8b64e346a337ae1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-2932000000-e7b92e9c5f2eef7360b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-05863de8b811aaf4f698Spectrum
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 IDHMDB0302089
FooDB IDFDB093521
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-8674
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10394547
ChEBI ID71498
PubChem Compound IDNot Available
Kegg Compound IDC16827
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16756345