1-O-Sinapoyl-beta-D-glucose (CHEM025567)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:28:27 UTC
Update Date2016-11-09 01:18:07 UTC
Accession NumberCHEM025567
Identification
Common Name1-O-Sinapoyl-beta-D-glucose
ClassSmall Molecule
DescriptionA glucosyl hydroxycinnamic acid that is the cinnamate ester obtained by the formal condensation of the carboxy group of trans-sinapic acid with the anomeric hydroxy group of beta-D-glucose.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-(2S,3R,4S,5S,6R)-TETRAHYDRO-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylATEChEBI
1-O-(trans-Sinapoyl)-beta-D-glucoseChEBI
1-O-[(2E)-Sinapoyl]-beta-D-glucopyranoseChEBI
1-O-[(2E)-Sinapoyl]-beta-D-glucoseChEBI
1-O-[(e)-Sinapoyl]-beta-D-glucopyranoseChEBI
1-O-Sinapoyl beta-D-glucosideChEBI
(e)-(2S,3R,4S,5S,6R)-TETRAHYDRO-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylic acidGenerator
1-O-(trans-Sinapoyl)-b-D-glucoseGenerator
1-O-(trans-Sinapoyl)-β-D-glucoseGenerator
1-O-[(2E)-Sinapoyl]-b-D-glucopyranoseGenerator
1-O-[(2E)-Sinapoyl]-β-D-glucopyranoseGenerator
1-O-[(2E)-Sinapoyl]-b-D-glucoseGenerator
1-O-[(2E)-Sinapoyl]-β-D-glucoseGenerator
1-O-[(e)-Sinapoyl]-b-D-glucopyranoseGenerator
1-O-[(e)-Sinapoyl]-β-D-glucopyranoseGenerator
1-O-Sinapoyl b-D-glucosideGenerator
1-O-Sinapoyl β-D-glucosideGenerator
1-O-Sinapoyl-b-D-glucoseGenerator
1-O-Sinapoyl-β-D-glucoseGenerator
Chemical FormulaC17H22O10
Average Molecular Mass386.351 g/mol
Monoisotopic Mass386.121 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Traditional Name1-O-sinapoyl-β-D-glucose
SMILESCOC1=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1O
InChI IdentifierInChI=1S/C17H22O10/c1-24-9-5-8(6-10(25-2)13(9)20)3-4-12(19)27-17-16(23)15(22)14(21)11(7-18)26-17/h3-6,11,14-18,20-23H,7H2,1-2H3/b4-3+/t11-,14-,15+,16-,17+/m1/s1
InChI KeyXRKBRPFTFKKHEF-DGDBGZAXSA-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
  • Hexose monosaccharide
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Methoxybenzene
  • Phenoxy compound
  • Anisole
  • Styrene
  • Phenol ether
  • Fatty acid ester
  • Alkyl aryl ether
  • Phenol
  • Fatty acyl
  • Benzenoid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility3.47 g/LALOGPS
logP-0.18ALOGPS
logP-0.52ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.14 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.4 m³·mol⁻¹ChemAxon
Polarizability38.15 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0493000000-d181a4379d88ad84ecfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1791000000-e9bf5fce535a5be499faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-5950000000-41195fd9f40a868a05feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0192000000-fcd55c080685f91b3b76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c00-3981000000-f3e747b19c399fb181f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9760000000-d21c1975568040eabeeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0239000000-c2e1bfdbc31bf38d7b8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0941000000-3a828f024d2190232f4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00n0-5981000000-3bd055bfd68f5eebc8d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0394000000-7393f48c33b217d2ce8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-1596000000-0b220c5804537001feceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-3894000000-ce7038479c30f0ab37efSpectrum
MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
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 IDHMDB0302379
FooDB IDFDB004337
Phenol Explorer IDNot Available
KNApSAcK IDC00013592
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444086
ChEBI ID16546
PubChem Compound IDNot Available
Kegg Compound IDC01175
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24241853
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24271623