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Record Information
Version2.0
Created at2022-04-28 00:33:14 UTC
Updated at2022-04-28 00:33:14 UTC
NP-MRD IDNP0054086
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-beta-D-Glucopyranosyl-5-hydroxy-2-(4-hydroxyphenyl)-7,8-dimethoxy-4H-1-benzopyran-4-one
DescriptionSwertisin 8-methyl ether belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Thus, swertisin 8-methyl ether is considered to be a flavonoid. 6-beta-D-Glucopyranosyl-5-hydroxy-2-(4-hydroxyphenyl)-7,8-dimethoxy-4H-1-benzopyran-4-one is found in Abrus precatorius , Abrus precatorius L. and Siphonoglossa sp.. Based on a literature review very few articles have been published on Swertisin 8-methyl ether.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H24O11
Average Mass476.4340 Da
Monoisotopic Mass476.13186 Da
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-7,8-dimethoxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
Traditional Name5-hydroxy-2-(4-hydroxyphenyl)-7,8-dimethoxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
CAS Registry NumberNot Available
SMILES
COC1=C2OC(=CC(=O)C2=C(O)C([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1OC)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C23H24O11/c1-31-21-15(20-19(30)18(29)16(27)13(8-24)34-20)17(28)14-11(26)7-12(33-22(14)23(21)32-2)9-3-5-10(25)6-4-9/h3-7,13,16,18-20,24-25,27-30H,8H2,1-2H3/t13-,16-,18+,19-,20+/m1/s1
InChI KeyLRJVZJKYYZEITI-NLMIBYRWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abrus precatoriusPlant
Abrus precatorius L.Plant
Siphonoglossa sp.Plant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid C-glycosides
Alternative Parents
Substituents
  • Flavonoid c-glycoside
  • 8-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • Chromone
  • C-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Phenol ether
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen 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
logP0.56ALOGPS
logP-0.062ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)7.43ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area175.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity116.98 m³·mol⁻¹ChemAxon
Polarizability47.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
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 IDC00006149
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102120185
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available