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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:50:08 UTC
Update Date2019-07-23 07:13:59 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
DescriptionLuteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-beta-D-glucuronide, also known as b-D-glucuronoside, 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. Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-beta-D-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-beta-D-glucuronide exists in all living organisms, ranging from bacteria to humans. 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
Data?1563866039
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
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
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
b-D-GlucuronosideHMDB
Β-D-glucuronosideHMDB
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,6S)-6-[4-(7-{[(2S,3R,4S,5S,6S)-6-carboxy-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}-5-hydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-[4-(7-{[(2S,3R,4S,5S,6S)-6-carboxy-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}-5-hydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]-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@@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
Description 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
  • 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

Source:

Biological location:

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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0072-0110609400-cbae178ac262219fed00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ki-0150905000-374eb75fce303e3fed43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-0360901100-9c9be8b9df349ea69241Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-1401329830-ae7a531bc91a0f59c237Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01rg-1900837600-8bbc6c888d867a5b1f51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-2910540100-d312e3426f8935117936Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB034579
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC04900
BioCyc IDLUTEOLIN-7-O-BETA-D-GLUCURONOSYL-1-2
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280752
PDB IDNot Available
ChEBI ID37645
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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