luteolin 7-O-β-D-diglucuronide (PAMDB120062)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120062
Identification
Name: luteolin 7-O-β-D-diglucuronide
Description:This compound belongs to the family of Flavonoid O-Glycosides. These are compounds containing a carbohydrate moiety which is o-glycosidically linked to one of the flavonoid backbones (2-phenylchromen-4-one, 3-phenylchromen-4-one or 4-phenylcoumarin).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid
  • luteolin 7-O-[β-D-glucuronosyl-(1→2)-β-D-glucuronide]
  • Luteolin 7-O-beta-D-diglucuronide
Chemical Formula: C27H24O18
Average Molecular Weight: 636.476
Monoisotopic Molecular Weight: 638.11194
InChI Key: PBBVWJQPAZYQDB-HBUFFLJYSA-L
InChI:InChI=1S/C27H26O18/c28-9-2-1-7(3-10(9)29)13-6-12(31)15-11(30)4-8(5-14(15)42-13)41-27-23(19(35)18(34)22(44-27)25(39)40)45-26-20(36)16(32)17(33)21(43-26)24(37)38/h1-6,16-23,26-30,32-36H,(H,37,38)(H,39,40)/p-2/t16-,17-,18-,19-,20+,21-,22-,23+,26-,27?/m0/s1
CAS number: Not Available
IUPAC Name:2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl (β-D-glucopyranosyluronic acid)-(1→2)-(β-D-glucopyranosiduronic acid)
Traditional IUPAC Name: (2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-6-carboxy-2-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES:C(C5(OC(OC1(C(C(C(C([O-])=O)OC1OC4(C=C3(C(C(C=C(C2(=CC=C(C(=C2)O)O))O3)=O)=C(C=4)O)))O)O))C(C(C5O)O)O))([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Phenylpropanoids and polyketides
Sub ClassFlavonoids
Direct Parent Flavonoid-7-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-7-o-glucuronide
  • Flavonoid-7-o-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Beta-hydroxy acid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Oxane
  • Hydroxy acid
  • Pyran
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Acetal
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.35 mg/mLALOGPS
logP0.93ALOGPS
logP-1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.6ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area299.66 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity139.19 m3·mol-1ChemAxon
Polarizability59.29 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
luteolin 7-O-β-D-diglucuronide + Hydrogen peroxide → a-radical-of-luteolin-7-iOi-diglucuronid + Water
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Magrane M, Consortium U: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [21447597 ]
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    HMDBHMDB60297
    CHEBI31787
    PUBCHEM25245471
    LIGAND-CPDC12632