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Record Information
Version2.0
Created at2021-06-19 21:32:50 UTC
Updated at2021-06-29 23:57:52 UTC
NP-MRD IDNP0030098
Secondary Accession NumbersNone
Natural Product Identification
Common Name4',5-dihydroxy-3',8-dimethoxyflavone 7-O-beta-D-glucopyranoside
Provided ByJEOL DatabaseJEOL Logo
Description4',5-Dihydroxy-3',8-dimethoxy-7-(beta-D-glucopyranosyloxy)flavone belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. 4',5-dihydroxy-3',8-dimethoxyflavone 7-O-beta-D-glucopyranoside is found in Kalanchoe pinnata and Setaria italica . 4',5-dihydroxy-3',8-dimethoxyflavone 7-O-beta-D-glucopyranoside was first documented in 2006 (Muzitano, M. F., et al.). Based on a literature review very few articles have been published on 4',5-Dihydroxy-3',8-dimethoxy-7-(beta-D-glucopyranosyloxy)flavone.
Structure
Thumb
Synonyms
ValueSource
4',5-Dihydroxy-3',8-dimethoxy-7-(b-D-glucopyranosyloxy)flavoneGenerator
4',5-Dihydroxy-3',8-dimethoxy-7-(β-D-glucopyranosyloxy)flavoneGenerator
Chemical FormulaC23H24O12
Average Mass492.4330 Da
Monoisotopic Mass492.12678 Da
IUPAC Name5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Name5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
CAS Registry NumberNot Available
SMILES
[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O[H])C([H])=C(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])C(OC([H])([H])[H])=C2O1
InChI Identifier
InChI=1S/C23H24O12/c1-31-14-5-9(3-4-10(14)25)13-6-11(26)17-12(27)7-15(21(32-2)22(17)33-13)34-23-20(30)19(29)18(28)16(8-24)35-23/h3-7,16,18-20,23-25,27-30H,8H2,1-2H3/t16-,18-,19+,20-,23-/m1/s1
InChI KeyXXUHDKDDHQURGH-PUIBNRJISA-N
Experimental Spectra
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Kalanchoe pinnataJEOL database
    • Muzitano, M. F., et al, Phytochemistry 67, 2071 (2006)
Setaria italicaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • 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
logP0.67ALOGPS
logP0.12ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.82ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area184.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity117.98 m³·mol⁻¹ChemAxon
Polarizability48.44 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID103884387
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14825846
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Muzitano, M. F., et al. (2006). Muzitano, M. F., et al, Phytochemistry 67, 2071 (2006). Phytochem..