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Record Information
Version2.0
Created at2022-03-17 21:02:20 UTC
Updated at2022-03-17 21:02:20 UTC
NP-MRD IDNP0048797
Secondary Accession NumbersNone
Natural Product Identification
Common NameDiosmetin 7-glucoside
DescriptionDiosmetin 7-O-beta-D-glucopyranoside, also known as 3',5,7-trihydroxy-4'-methoxyflavone, 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. Diosmetin 7-O-beta-D-glucopyranoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Diosmetin 7-O-beta-D-glucopyranoside has been detected, but not quantified in, a few different foods, such as cornmints, spearmints, and sweet marjorams. This could make diosmetin 7-O-beta-D-glucopyranoside a potential biomarker for the consumption of these foods. Diosmetin 7-glucoside is found in Chrysanthemum indicum , Ferulopsis hystrix and Petroselinum crispum. Diosmetin 7-O-beta-D-glucopyranoside is isolated from Galium species, Chrysanthemum sp.
Structure
Thumb
Synonyms
ValueSource
Diosmetin 7-O-b-D-glucopyranosideGenerator
Diosmetin 7-O-β-D-glucopyranosideGenerator
3',5,7-Trihydroxy-4'-methoxyflavoneHMDB
7-O-b-D-GlucopyranosideHMDB
Chemical FormulaC22H22O11
Average Mass462.4035 Da
Monoisotopic Mass462.11621 Da
IUPAC Name5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Name5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
CAS Registry Number20126-59-4
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O)C=C(OC3OC(CO)C(O)C(O)C3O)C=C2O1
InChI Identifier
InChI=1S/C22H22O11/c1-30-14-3-2-9(4-11(14)24)15-7-13(26)18-12(25)5-10(6-16(18)32-15)31-22-21(29)20(28)19(27)17(8-23)33-22/h2-7,17,19-25,27-29H,8H2,1H3
InChI KeyWKUHPOMCLBLCOV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Chrysanthemum indicumPlant
Ferulopsis hystrixLOTUS Database
Mentha arvensisFooDB
Mentha spicataFooDB
Origanum majoranaFooDB
Petroselinum crispumLOTUS Database
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
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Phenol
  • Pyranone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Acetal
  • Polyol
  • Oxacycle
  • 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
logP0.64ALOGPS
logP0.28ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area175.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.52 m³·mol⁻¹ChemAxon
Polarizability45.33 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037451
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016510
KNApSAcK IDC00004357
Chemspider ID4527363
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5378562
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available