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Record Information
Version2.0
Created at2022-04-28 00:23:52 UTC
Updated at2022-04-28 00:23:52 UTC
NP-MRD IDNP0053874
Secondary Accession NumbersNone
Natural Product Identification
Common NameKaempferol 3-[2''',3''',5'''-triacetyl-alpha-L-arabinofuranosyl-(1->6)-glucoside
Description[(2R,3S,4R,5R)-3,4-bis(acetyloxy)-5-{[(2S,3S,4R,5S,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}oxolan-2-yl]methyl acetate belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-[2''',3''',5'''-triacetyl-alpha-L-arabinofuranosyl-(1->6)-glucoside is found in Calluna vulgaris . Based on a literature review very few articles have been published on [(2R,3S,4R,5R)-3,4-bis(acetyloxy)-5-{[(2S,3S,4R,5S,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}oxolan-2-yl]methyl acetate.
Structure
Thumb
Synonyms
ValueSource
[(2R,3S,4R,5R)-3,4-Bis(acetyloxy)-5-{[(2S,3S,4R,5S,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}oxolan-2-yl]methyl acetic acidGenerator
Chemical FormulaC32H34O18
Average Mass706.6060 Da
Monoisotopic Mass706.17451 Da
IUPAC Name[(2R,3S,4R,5R)-3,4-bis(acetyloxy)-5-{[(2S,3S,4R,5S,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}oxolan-2-yl]methyl acetate
Traditional Name[(2R,3S,4R,5R)-3,4-bis(acetyloxy)-5-{[(2S,3S,4R,5S,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}oxolan-2-yl]methyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC[C@H]1O[C@@H](OC[C@@H]2O[C@@H](OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC=C(O)C=C3)[C@@H](O)[C@H](O)[C@@H]2O)[C@H](OC(C)=O)[C@H]1OC(C)=O
InChI Identifier
InChI=1S/C32H34O18/c1-12(33)43-11-21-28(45-13(2)34)30(46-14(3)35)32(49-21)44-10-20-23(39)25(41)26(42)31(48-20)50-29-24(40)22-18(38)8-17(37)9-19(22)47-27(29)15-4-6-16(36)7-5-15/h4-9,20-21,23,25-26,28,30-32,36-39,41-42H,10-11H2,1-3H3/t20-,21+,23+,25+,26-,28-,30+,31-,32+/m0/s1
InChI KeyGNUSJIOAQXUIRK-XCVWSCADSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Calluna vulgarisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Tricarboxylic acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP1.89ALOGPS
logP0.34ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area263.5 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity161.2 m³·mol⁻¹ChemAxon
Polarizability65.97 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162873350
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available