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Record Information
Version2.0
Created at2022-04-27 23:43:07 UTC
Updated at2022-04-27 23:43:07 UTC
NP-MRD IDNP0052788
Secondary Accession NumbersNone
Natural Product Identification
Common Name5,7,8-Trihydroxyflavone 5-glucoside
Description7,8-Dihydroxy-2-phenyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Thus, 7,8-dihydroxy-2-phenyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one is considered to be a flavonoid. 5,7,8-Trihydroxyflavone 5-glucoside is found in Pyracantha coccinea. Based on a literature review very few articles have been published on 7,8-dihydroxy-2-phenyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H20O10
Average Mass432.3810 Da
Monoisotopic Mass432.10565 Da
IUPAC Name7,8-dihydroxy-2-phenyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Name7,8-dihydroxy-2-phenyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=C3C(=O)C=C(OC3=C(O)C(O)=C2)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H20O10/c22-8-14-17(26)18(27)19(28)21(31-14)30-13-7-11(24)16(25)20-15(13)10(23)6-12(29-20)9-4-2-1-3-5-9/h1-7,14,17-19,21-22,24-28H,8H2/t14-,17-,18+,19-,21-/m1/s1
InChI KeyWRNOCNYTWGRQMW-FKRBRYKNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pyracantha coccineaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid-5-o-glycoside
  • Flavonoid o-glycoside
  • 7-hydroxyflavonoid
  • 8-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Vinylogous ester
  • Heteroaromatic compound
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.59ALOGPS
logP-0.21ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.71ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.06 m³·mol⁻¹ChemAxon
Polarizability41.95 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162928716
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References