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Record Information
Version3.6
Creation Date2013-05-17 00:50:08 UTC
Update Date2016-02-11 08:03:07 UTC
HMDB IDHMDB60296
Secondary Accession NumbersNone
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
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=1/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+/s2
InChI KeyInChIKey=AEYXZGCDWDUIKX-GEBQAWBBNA-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
  • Fatty acyl glycoside
  • 5-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Tricarboxylic acid or derivatives
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Phenol ether
  • Pyranone
  • Phenol
  • Beta-hydroxy acid
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Oxane
  • Hydroxy acid
  • 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 Solubility4.6 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity171.2 m3·mol-1ChemAxon
Polarizability74.88 Å3ChemAxon
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
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 ID4444324
KEGG Compound IDC04900
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60296
Metagene LinkHMDB60296
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, 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