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Record Information
Version2.0
Created at2022-09-06 22:57:15 UTC
Updated at2022-09-06 22:57:15 UTC
NP-MRD IDNP0239372
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,3s,4s,5r,6s)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)oxane-2-carboxylic acid
Description3-(2-O-Galloyl-beta-D-glucurono pyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position. Based on a literature review very few articles have been published on 3-(2-O-Galloyl-beta-D-glucurono pyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one.
Structure
Thumb
Synonyms
ValueSource
3-(2-O-Galloyl-b-D-glucurono pyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneGenerator
3-(2-O-Galloyl-β-D-glucurono pyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneGenerator
Chemical FormulaC28H22O16
Average Mass614.4680 Da
Monoisotopic Mass614.09078 Da
IUPAC Name(2S,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@H]1[C@H](O)[C@H](O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=O
InChI Identifier
InChI=1S/C28H22O16/c29-11-3-1-9(2-4-11)22-23(19(35)17-13(31)7-12(30)8-16(17)41-22)43-28-25(21(37)20(36)24(44-28)26(38)39)42-27(40)10-5-14(32)18(34)15(33)6-10/h1-8,20-21,24-25,28-34,36-37H,(H,38,39)/t20-,21-,24-,25+,28+/m0/s1
InChI KeyOYBKGCKIYYHOJN-DTCGYDHASA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-3-o-glucuronide
  • Flavonoid-3-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 1-o-glucuronide
  • O-glucuronide
  • Galloyl ester
  • Glucuronic acid or derivatives
  • Gallic acid or derivatives
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Chromone
  • Glycosyl compound
  • P-hydroxybenzoic acid alkyl ester
  • O-glycosyl compound
  • Benzoate ester
  • Benzopyran
  • 1-benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • Pyranone
  • Phenol
  • Beta-hydroxy acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Oxane
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Carboxylic acid
  • Acetal
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP2.06ChemAxon
pKa (Strongest Acidic)2.57ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area270.2 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity142.93 m³·mol⁻¹ChemAxon
Polarizability56.31 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 Compound102033017
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]