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Record Information
Version2.0
Created at2022-09-02 18:46:23 UTC
Updated at2022-09-02 18:46:24 UTC
NP-MRD IDNP0160757
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl acetate
DescriptionDiosmetin 7-apiosyl-(1->2)-(6''-acetylglucoside) 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. Thus, diosmetin 7-apiosyl-(1->2)-(6''-acetylglucoside) is considered to be a flavonoid. [(2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl acetate is found in Paullinia pinnata. Based on a literature review very few articles have been published on Diosmetin 7-apiosyl-(1->2)-(6''-acetylglucoside).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC29H32O16
Average Mass636.5590 Da
Monoisotopic Mass636.16903 Da
IUPAC Name[(2R,3S,4S,5R,6S)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetate
Traditional Name[(2R,3S,4S,5R,6S)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl acetate
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C=C1O)C1=CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3OC[C@](O)(CO)[C@H]3O)C=C2O1
InChI Identifier
InChI=1S/C29H32O16/c1-12(31)40-9-21-23(35)24(36)25(45-28-26(37)29(38,10-30)11-41-28)27(44-21)42-14-6-16(33)22-17(34)8-19(43-20(22)7-14)13-3-4-18(39-2)15(32)5-13/h3-8,21,23-28,30,32-33,35-38H,9-11H2,1-2H3/t21-,23-,24+,25-,26+,27-,28+,29-/m1/s1
InChI KeyFGALOZIRMNCSRZ-MIKDDSNXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Paullinia pinnataLOTUS 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
  • Hydroxyflavonoid
  • Flavone
  • 5-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Anisole
  • Phenol ether
  • Phenoxy compound
  • Methoxybenzene
  • Pyranone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Heteroaromatic compound
  • Tertiary alcohol
  • Tetrahydrofuran
  • Vinylogous acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Ether
  • Primary alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • 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
logP0.72ALOGPS
logP-0.55ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.31ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area240.36 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity147.34 m³·mol⁻¹ChemAxon
Polarizability62.53 ųChemAxon
Number of Rings5ChemAxon
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 IDC00013682
Chemspider ID8803213
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10627850
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]