Show more...
Record Information
Version2.0
Created at2022-04-28 00:31:47 UTC
Updated at2022-04-28 00:31:47 UTC
NP-MRD IDNP0054051
Secondary Accession NumbersNone
Natural Product Identification
Common Name5,7,3',4',5'-Pentahydroxyflavone 8-C-glucopyranoside
Description5,7-Dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Thus, 5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one is considered to be a flavonoid. 5,7,3',4',5'-Pentahydroxyflavone 8-C-glucopyranoside is found in Trichomanes venosum. Based on a literature review very few articles have been published on 5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H20O12
Average Mass464.3790 Da
Monoisotopic Mass464.09548 Da
IUPAC Name5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
Traditional Name5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(3,4,5-trihydroxyphenyl)chromen-4-one
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C21H20O12/c22-5-13-17(29)18(30)19(31)21(33-13)15-8(24)3-7(23)14-9(25)4-12(32-20(14)15)6-1-10(26)16(28)11(27)2-6/h1-4,13,17-19,21-24,26-31H,5H2/t13-,17-,18+,19-,21+/m1/s1
InChI KeyPDURHZNFDMIFDU-FFYOZGDPSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Trichomanes venosumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • C-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Benzenetriol
  • Pyrogallol derivative
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Pyran
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkyl ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • 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
logP0.28ALOGPS
logP-0.66ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)6.17ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area217.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity109.99 m³·mol⁻¹ChemAxon
Polarizability43.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
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 Compound162895947
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References