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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:50:14 UTC
Update Date2017-12-07 16:43:13 UTC
HMDB IDHMDB0060297
Secondary Accession Numbers
  • HMDB60297
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
Luteolin-7-O-[b-D-glucuronosyl-(1->2)-b-D-glucuronide]Generator
Luteolin-7-O-[β-D-glucuronosyl-(1->2)-β-D-glucuronide]Generator
Luteolin-7-O-[b-glucuronosyl-(1->2)-b-glucuronide]Generator
Luteolin-7-O-[β-glucuronosyl-(1->2)-β-glucuronide]Generator
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=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)/t16-,17-,18-,19-,20+,21-,22-,23+,26-,27+/m0/s1
InChI KeyPBBVWJQPAZYQDB-DBFWEQBMSA-N
Chemical 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassFlavonoids
Direct ParentFlavonoid-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity139.19 m³·mol⁻¹ChemAxon
Polarizability59.29 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-3230092000-ea586362caa9811d734aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007a-0190708000-3d49ae4f96ee951e9a47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190300000-58045aa21bff6be8fde8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0590100000-3a3f84a9e4792f8e9f1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-2683988000-404d4bc0c3bffae7c491View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2691521000-3e459376349ced77a414View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000m-3890210000-d1d3d2eefee06ac61d1eView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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
      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: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed: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