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Record Information
Version2.0
Created at2022-03-17 21:02:54 UTC
Updated at2022-03-17 21:02:55 UTC
NP-MRD IDNP0048834
Secondary Accession NumbersNone
Natural Product Identification
Common NameDiosmetin 6-C-glucoside
Description6-Beta-D-Glucopyranosyldiosmetin 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. 6-Beta-D-Glucopyranosyldiosmetin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6-beta-D-Glucopyranosyldiosmetin has been detected, but not quantified in, citrus and lemons. Diosmetin 6-C-glucoside is found in Parkinsonia aculeata . This could make 6-beta-D-glucopyranosyldiosmetin a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
6-b-D-GlucopyranosyldiosmetinGenerator
6-Β-D-glucopyranosyldiosmetinGenerator
6-beta-D-Glucopyranosyl-5,7,3'-trihydroxy-4'-methoxyflavoneHMDB
6-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-oneHMDB
6-C-beta-D-GlucopyranosyldiosmetinHMDB
Chemical FormulaC22H22O11
Average Mass462.4035 Da
Monoisotopic Mass462.11621 Da
IUPAC Name5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
Traditional Name5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
CAS Registry Number15822-82-9
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C(C1OC(CO)C(O)C(O)C1O)=C2O
InChI Identifier
InChI=1S/C22H22O11/c1-31-12-3-2-8(4-9(12)24)13-5-10(25)16-14(32-13)6-11(26)17(19(16)28)22-21(30)20(29)18(27)15(7-23)33-22/h2-6,15,18,20-24,26-30H,7H2,1H3
InChI KeyADVFPEKLSDNTRV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus limonFooDB
Parkinsonia aculeataPlant
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
  • 4p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • C-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Methoxybenzene
  • Anisole
  • Phenol ether
  • Phenoxy compound
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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
logP0.51ALOGPS
logP-0.21ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity112.5 m³·mol⁻¹ChemAxon
Polarizability45.67 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037567
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016652
KNApSAcK IDC00006123
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14861262
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available