Show more...
Record Information
Version2.0
Created at2022-04-27 23:44:25 UTC
Updated at2022-04-27 23:44:25 UTC
NP-MRD IDNP0052819
Secondary Accession NumbersNone
Natural Product Identification
Common Name5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-8-yl beta-D-glucopyranosiduronic acid
Description8-Hydroxyluteolin 3'-methyl ether 8-glucuronide belongs to the class of organic compounds known as flavonoid-8-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C8-position. Thus, 8-hydroxyluteolin 3'-methyl ether 8-glucuronide is considered to be a flavonoid. 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-8-yl beta-D-glucopyranosiduronic acid is found in Gratiola officinalis . Based on a literature review very few articles have been published on 8-hydroxyluteolin 3'-methyl ether 8-glucuronide.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H20O13
Average Mass492.3890 Da
Monoisotopic Mass492.09039 Da
IUPAC Name(2S,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC=C1O)C1=CC(=O)C2=C(O)C=C(O)C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)=C2O1
InChI Identifier
InChI=1S/C22H20O13/c1-32-13-4-7(2-3-8(13)23)12-6-10(25)14-9(24)5-11(26)18(19(14)33-12)34-22-17(29)15(27)16(28)20(35-22)21(30)31/h2-6,15-17,20,22-24,26-29H,1H3,(H,30,31)/t15-,16-,17+,20-,22+/m0/s1
InChI KeyXMUSFCCVYDPKCR-NTKSAMNMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Gratiola officinalisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-8-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C8-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-8-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-8-o-glucuronide
  • Flavonoid-8-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Beta-hydroxy acid
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • 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
logP1.37ALOGPS
logP0.3ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.57ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area212.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.37 m³·mol⁻¹ChemAxon
Polarizability45.84 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00004519
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163106584
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available