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trans-cinnamoyl-β-D-glucoside (FDB031210)

Record Information
Version1.0
Creation date2015-05-07 21:19:57 UTC
Update date2019-11-26 03:22:11 UTC
Primary IDFDB031210
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-cinnamoyl-β-D-glucoside
DescriptionTrans-cinnamoyl-β-d-glucoside, also known as 1-O-trans-cinnamoyl-beta-D-glucopyranose, is a member of the class of compounds known as O-cinnamoyl glycosides. O-cinnamoyl glycosides 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. Trans-cinnamoyl-β-d-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Trans-cinnamoyl-β-d-glucoside can be found in a number of food items such as angelica, cherry tomato, garden cress, and yam, which makes trans-cinnamoyl-β-d-glucoside a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H18O7
IUPAC name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-phenylprop-2-enoate
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
Isomeric 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
Average Molecular Weight310.302
Monoisotopic Molecular Weight310.10525292
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-0911000000-212d9bb58e95a88e1d4c2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-1900000000-cc5a5355829ad21ec7cf2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ued-5900000000-281b4430705fb1f53a002019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0901000000-b69f82476eaaa0eb2d652019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r2-2900000000-a2d6695187f94db5a9072019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-5900000000-ab8177d19aa74b8027792019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0913000000-8ddf8e447c8661be445a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-25fec19e3267ef1e43522021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-6c4496f7411e8f6944762021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0901000000-12a261ca159e96e33fb12021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-3d861b97a24e8d558c0d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9500000000-d9062dabb9a0e48521b42021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference