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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:50:08 UTC
Update Date2017-12-07 16:43:06 UTC
HMDB IDHMDB0060296
Secondary Accession Numbers
  • HMDB60296
Metabolite Identification
Common NameLuteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-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
2-[4-(beta-D-Glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranosiduronic acidChEBI
Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-beta-D-glucuronideChEBI
2-[4-(b-D-Glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-b-D-glucopyranuronosyl-b-D-glucopyranosiduronateGenerator
2-[4-(b-D-Glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-b-D-glucopyranuronosyl-b-D-glucopyranosiduronic acidGenerator
2-[4-(beta-D-Glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranosiduronateGenerator
2-[4-(β-D-glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronateGenerator
2-[4-(β-D-glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acidGenerator
b-D-GlucuronosideGenerator
β-D-glucuronosideGenerator
Luteolin 7-O-[b-D-glucuronosyl-(1->2)-b-D-glucuronide]-4'-O-b-D-glucuronideGenerator
Luteolin 7-O-[β-D-glucuronosyl-(1->2)-β-D-glucuronide]-4'-O-β-D-glucuronideGenerator
Chemical FormulaC33H34O24
Average Molecular Weight814.6087
Monoisotopic Molecular Weight814.144002016
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-6-carboxy-2-{[2-(4-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Nameluteolin
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@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C=C2)C(O)=O)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C33H34O24/c34-9-3-7(1-2-12(9)53-31-22(43)16(37)18(39)24(54-31)28(45)46)13-6-11(36)15-10(35)4-8(5-14(15)52-13)51-33-27(21(42)20(41)26(56-33)30(49)50)57-32-23(44)17(38)19(40)25(55-32)29(47)48/h1-6,16-27,31-35,37-44H,(H,45,46)(H,47,48)(H,49,50)/t16-,17-,18-,19-,20-,21-,22+,23+,24-,25-,26-,27+,31+,32-,33+/m0/s1
InChI KeyAEYXZGCDWDUIKX-OFFAAIFBSA-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
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • Disaccharide
  • Benzopyran
  • 1-benzopyran
  • Tricarboxylic acid or derivatives
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Pyran
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen 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 Solubility4.6 g/LALOGPS
logP0.27ALOGPS
logP-2.9ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.45ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area395.88 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity171.2 m³·mol⁻¹ChemAxon
Polarizability74.88 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0072-0110609400-cbae178ac262219fed00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ki-0150905000-374eb75fce303e3fed43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-0360901100-9c9be8b9df349ea69241View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-1401329830-ae7a531bc91a0f59c237View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01rg-1900837600-8bbc6c888d867a5b1f51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-2910540100-d312e3426f8935117936View 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 ID4444324
      KEGG Compound IDC04900
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound5280752
      PDB IDNot Available
      ChEBI ID37645
      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