trans-p-Feruloyl-beta-D-glucopyranoside (CHEM023914)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:22:07 UTC
Update Date2016-11-09 01:17:48 UTC
Accession NumberCHEM023914
Identification
Common Nametrans-p-Feruloyl-beta-D-glucopyranoside
ClassSmall Molecule
DescriptionA beta-D-glucoside resulting from the formal condensation of the carboxy group of ferulic acid with the anomeric hydroxy group of beta-D-glucose.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-1-O-Feruloyl-beta-D-glucopyranoseChEBI
(e)-4'-Hydroxy-3'-methoxycinnamoyl-beta-D-glucopyranoseChEBI
1-Feruloyl-D-glucoseChEBI
1-O-(e)-Feruloyl-beta-D-glucoseChEBI
1-O-(e)-p-Feruloyl-beta-D-glucopyranoseChEBI
1-O-[(e)-Feruloyl]-beta-D-glucoseChEBI
1-O-trans-Feruloyl-beta-D-glucopyranosideChEBI
Ferulic acid beta-D-glucopyranosyl esterChEBI
trans-p-Feruloyl-beta-D-glucopyranosideChEBI
(e)-1-O-Feruloyl-b-D-glucopyranoseGenerator
(e)-1-O-Feruloyl-β-D-glucopyranoseGenerator
(e)-4'-Hydroxy-3'-methoxycinnamoyl-b-D-glucopyranoseGenerator
(e)-4'-Hydroxy-3'-methoxycinnamoyl-β-D-glucopyranoseGenerator
1-O-(e)-Feruloyl-b-D-glucoseGenerator
1-O-(e)-Feruloyl-β-D-glucoseGenerator
1-O-(e)-p-Feruloyl-b-D-glucopyranoseGenerator
1-O-(e)-p-Feruloyl-β-D-glucopyranoseGenerator
1-O-[(e)-Feruloyl]-b-D-glucoseGenerator
1-O-[(e)-Feruloyl]-β-D-glucoseGenerator
1-O-trans-Feruloyl-b-D-glucopyranosideGenerator
1-O-trans-Feruloyl-β-D-glucopyranosideGenerator
Ferulate b-D-glucopyranosyl esterGenerator
Ferulate beta-D-glucopyranosyl esterGenerator
Ferulate β-D-glucopyranosyl esterGenerator
Ferulic acid b-D-glucopyranosyl esterGenerator
Ferulic acid β-D-glucopyranosyl esterGenerator
trans-p-Feruloyl-b-D-glucopyranosideGenerator
trans-p-Feruloyl-β-D-glucopyranosideGenerator
1-O-Feruloyl-b-D-glucoseGenerator
1-O-Feruloyl-β-D-glucoseGenerator
1-O-(trans-Feruloyl)-beta-D-glucoseChEBI
1-O-(trans-Feruloyl)-b-D-glucoseGenerator
1-O-(trans-Feruloyl)-β-D-glucoseGenerator
Chemical FormulaC16H20O9
Average Molecular Mass356.325 g/mol
Monoisotopic Mass356.111 g/mol
CAS Registry Number117405-51-3
IUPAC Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
SMILESCOC1=C(O)C=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1
InChI IdentifierInChI=1S/C16H20O9/c1-23-10-6-8(2-4-9(10)18)3-5-12(19)25-16-15(22)14(21)13(20)11(7-17)24-16/h2-6,11,13-18,20-22H,7H2,1H3/b5-3+/t11-,13-,14+,15-,16+/m1/s1
InChI KeyJWRQVQWBNRGGPK-PMQCXRHVSA-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 or derivatives
  • Hexose monosaccharide
  • Cinnamic acid ester
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Phenol
  • Alkyl aryl ether
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Polyol
  • Ether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • 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 Solubility5.98 g/LALOGPS
logP-0.44ALOGPS
logP-0.36ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.94 m³·mol⁻¹ChemAxon
Polarizability34.31 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, Positivesplash10-004j-0902000000-24227394506e8ab64f52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-eb4cf06e241af96f6c24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-3900000000-da7b3d7b488f8e9051ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0902000000-37a716587e1315008931Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01tc-1900000000-39bdfa7a1ba96134e42eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-6900000000-322729ebffe36b54c807Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0709000000-ce3525d91657e72b8edcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-98ca975741f21b42f0fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2930000000-4f55cd0374f41611f3e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-0906000000-4f36c3d8b3ada7e9e659Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kcs-1913000000-bf251348657a4fd3779fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1901000000-405abedc8dbb2395567eSpectrum
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 IDHMDB0301952
FooDB IDFDB001666
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-15281
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID26336946
ChEBI ID81321
PubChem Compound IDNot Available
Kegg Compound IDC17759
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12060275
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12895536
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15740069
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16666663
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16756345
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20971893