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Record Information
Version3.6
Creation Date2013-05-17 00:50:14 UTC
Update Date2016-02-11 08:03:08 UTC
HMDB IDHMDB60297
Secondary Accession NumbersNone
Metabolite Identification
Common NameLuteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]
DescriptionThis 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
Synonyms
ValueSource
Luteolin 7-O-beta-D-diglucuronideChEBI
Luteolin-7-O-[beta-glucuronosyl-(1->2)-beta-glucuronide]ChEBI
Luteolin 7-O-b-D-diglucuronideGenerator
Luteolin 7-O-β-D-diglucuronideGenerator
Chemical FormulaC27H26O18
Average Molecular Weight638.4845
Monoisotopic Molecular Weight638.111914028
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-6-carboxy-2-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional 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
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H](O[C@H]2OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC(O)=C(O)C=C2)C(O)=O)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1/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)/t16-,17-,18-,19-,20+,21-,22-,23+,26-,27+/s2
InChI KeyInChIKey=PBBVWJQPAZYQDB-OYBQOXGENA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-7-o-glucuronide
  • Flavonoid-7-o-glycoside
  • Hydroxyflavonoid
  • Flavone
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • 1,2-diphenol
  • Pyranone
  • Phenol
  • Beta-hydroxy acid
  • Benzenoid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Saccharide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
OriginNot Available
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot 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
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
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4445350
KEGG Compound IDC12632
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60297
Metagene LinkHMDB60297
METLIN IDNot Available
PubChem Compound5282153
PDB IDNot Available
ChEBI ID60077
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Plays an important role in the degradation of dermatan and keratan sulfates.
Gene Name:
GUSB
Uniprot ID:
P08236
Molecular weight:
74731.46
Reactions
Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-beta-D-glucuronide + Water → Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide] + D-Glucuronic aciddetails