trans-cinnamoyl-β-D-glucoside (CHEM042427)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 02:02:34 UTC
Update Date2016-11-09 01:22:40 UTC
Accession NumberCHEM042427
Identification
Common Nametrans-cinnamoyl-β-D-glucoside
ClassSmall Molecule
DescriptionAn O-acyl carbohydrate consisting of beta-D-glucose carrying a O-trans-cinnamoyl group at the anomeric position.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-O-(trans-Cinnamoyl)-beta-D-glucoseChEBI
trans-Cinnamoyl beta-D-glucosideChEBI
1-O-(trans-Cinnamoyl)-b-D-glucoseGenerator
1-O-(trans-Cinnamoyl)-β-D-glucoseGenerator
trans-Cinnamoyl b-D-glucosideGenerator
trans-Cinnamoyl β-D-glucosideGenerator
1-O-trans-Cinnamoyl-b-D-glucopyranoseGenerator
1-O-trans-Cinnamoyl-β-D-glucopyranoseGenerator
1-O-trans-Cinnamoyl-beta-D-glucopyranoseKEGG
Chemical FormulaC15H18O7
Average Molecular Mass310.302 g/mol
Monoisotopic Mass310.105 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-phenylprop-2-enoate
Traditional Nametrans-cinnamoyl β-D-glucoside
SMILES[H]\C(=C(\[H])C1=CC=CC=C1)C(=O)O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O
InChI IdentifierInChI=1S/C15H18O7/c16-8-10-12(18)13(19)14(20)15(21-10)22-11(17)7-6-9-4-2-1-3-5-9/h1-7,10,12-16,18-20H,8H2/b7-6+/t10-,12-,13+,14-,15+/m1/s1
InChI KeyCJGRGYBLAHPYOM-HOLMNUNMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-cinnamoyl glycosides. These are o-glycoside derivatives of cinnamic acid. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acid esters
Direct ParentO-cinnamoyl glycosides
Alternative Parents
Substituents
  • O-cinnamoyl glycoside
  • Hexose monosaccharide
  • Styrene
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Monosaccharide
  • Fatty acyl
  • Oxane
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Primary alcohol
  • 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 Solubility9.42 g/LALOGPS
logP-0.41ALOGPS
logP0.1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.49 m³·mol⁻¹ChemAxon
Polarizability30.26 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, Positivesplash10-01qa-0911000000-212d9bb58e95a88e1d4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-1900000000-cc5a5355829ad21ec7cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ued-5900000000-281b4430705fb1f53a00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0901000000-b69f82476eaaa0eb2d65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r2-2900000000-a2d6695187f94db5a907Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-5900000000-ab8177d19aa74b802779Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0913000000-8ddf8e447c8661be445aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-25fec19e3267ef1e4352Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-6c4496f7411e8f694476Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0901000000-12a261ca159e96e33fb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-3d861b97a24e8d558c0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9500000000-d9062dabb9a0e48521b4Spectrum
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 IDHMDB0304505
FooDB IDFDB031210
Phenol Explorer IDNot Available
KNApSAcK IDC00058319
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444252
ChEBI ID16279
PubChem Compound IDNot Available
Kegg Compound IDC04164
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11330708
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11409967