Glyphoside (CHEM031814)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:56:24 UTC
Update Date2016-11-09 01:19:20 UTC
Accession NumberCHEM031814
Identification
Common NameGlyphoside
ClassSmall Molecule
Description2''-O-Acetylhyperin is found in alcoholic beverages. 2''-O-Acetylhyperin is a constituent of Hypericum perforatum (St John's wort).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetic acidHMDB
Chemical FormulaC23H22O13
Average Molecular Mass506.413 g/mol
Monoisotopic Mass506.106 g/mol
CAS Registry Number11029-60-0
IUPAC Name2-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate
Traditional Name2-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate
SMILESCC(=O)OC1C(O)C(O)C(CO)OC1OC1=C(OC2=C(C(O)=CC(O)=C2)C1=O)C1=CC(O)=C(O)C=C1
InChI IdentifierInChI=1S/C23H22O13/c1-8(25)33-22-19(32)17(30)15(7-24)35-23(22)36-21-18(31)16-13(29)5-10(26)6-14(16)34-20(21)9-2-3-11(27)12(28)4-9/h2-6,15,17,19,22-24,26-30,32H,7H2,1H3
InChI KeyAIHKAQUFJMNPAR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility1.28 g/LALOGPS
logP1.47ALOGPS
logP0.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area212.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity118.43 m³·mol⁻¹ChemAxon
Polarizability47.63 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aba-9211500000-9c38c9c3cfaf4d98b9c3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000l-9220024000-54a4f6160b1b6e0d8e23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1139730000-5f47221602519551414aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0159200000-43f5cbb3ea57d6bbc1c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-2963000000-a6e2b3ba887e42531c0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-8228960000-1bbdc15eeb35c1648803Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9247300000-93409e682f036698277dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9221000000-9e2cd85e54b767c0ed71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-9c372364828e1e036170Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0005090000-24b8b64d450ad1a64794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0019010000-a26850d0977d84a765cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009020000-6f422989e97c37eb5efcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-14i0-0009090000-bb0e9e847f0a7d659154Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0009000000-58b2754f892c40f07699Spectrum
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 IDHMDB0038465
FooDB IDFDB017824
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID74978233
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.