beta-D-Glucuronoside (ECMDB23833) (M2MDB004716)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (36)
Record Information
Version2.0
Creation Date2015-06-04 17:53:42 -0600
Update Date2015-08-05 16:22:05 -0600
Secondary Accession Numbers
  • ECMDB23833
Identification
Name:beta-D-Glucuronoside
DescriptionA substance produced by linking glucuronic acid to another substance via a glycosidic bond
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-[4-(b-D-Glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-b-D-glucopyranuronosyl-b-D-glucopyranosiduronate
  • 2-[4-(b-D-Glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-b-D-glucopyranuronosyl-b-D-glucopyranosiduronic acid
  • 2-[4-(beta-D-Glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranosiduronate
  • 2-[4-(beta-D-Glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranosiduronic acid
  • 2-[4-(β-D-Glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronate
  • 2-[4-(β-D-Glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid
  • b-D-Glucuronoside
  • Luteolin 7-O-[b-D-glucuronosyl-(1->2)-b-D-glucuronide]-4'-O-b-D-glucuronide
  • Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-beta-D-glucuronide
  • Luteolin 7-O-[β-D-glucuronosyl-(1->2)-β-D-glucuronide]-4'-O-β-D-glucuronide
  • β-D-Glucuronoside
Chemical Formula:C33H34O24
Weight:Average: 814.6087
Monoisotopic: 814.144002016
InChI Key:AEYXZGCDWDUIKX-OFFAAIFBSA-N
InChI: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
CAS number:Not Available
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 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-oxochromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
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
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
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Water + beta-D-Glucuronoside + beta-D-Glucuronoside <> D-Glucuronic acid + Alcohol + Alcohol
SMPDB Pathways:
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0000900040-af3eee53e8867f40a69aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000900000-0c115b9e354ac70b358aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000900000-0c115b9e354ac70b358aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900060-4160a262c58ba86e274eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-ebe531f582a3b02ab887View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000900000-1ceca2a985b85bd5d307View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID37645
HMDB IDHMDB0060296
Pubchem Compound ID5280752
Kegg IDC03033
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Beta-glucuronidase
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
A beta-D-glucuronoside + H(2)O = D-glucuronate + an alcohol
Gene Name:
uidA
Uniprot ID:
P05804
Molecular weight:
68447
Reactions
A beta-D-glucuronoside + H(2)O = D-glucuronate + an alcohol.