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Bilirubin diglucuronide (M2MDB000489)

Record Information
Version2.0
Creation Date2012-05-31 13:58:28 -0600
Update Date2015-09-13 12:56:12 -0600
Secondary Accession Numbers
  • ECMDB03325
Identification
Name:Bilirubin diglucuronide
DescriptionBilirubin diglucuronide is a water soluble version of bilirubin. E. coli living in the mammalian gut can use this compound as a substrate for growth. Bilirubin glucuronides are water-soluble.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2S,3S,4S,5R,6S)-6-[3-[2-[[3-[2-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-oxan-2-yl]oxycarbonylethyl]-5-[(E)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(E)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoyloxy]-3,4,5-trihydroxy-oxane-2-carboxylate
  • (2S,3S,4S,5R,6S)-6-[3-[2-[[3-[2-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-oxan-2-yl]oxycarbonylethyl]-5-[(E)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(E)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoyloxy]-3,4,5-trihydroxy-oxane-2-carboxylic acid
  • Bilirubin β-diglucuronide
  • Bilirubin b-diglucuronide
  • Bilirubin beta-diglucuronide
  • Bilirubin β-diglucuronide
  • Bilirubin-bisglucuronoside
  • Bis(glucosyluronate)bilirubin
  • Bis(glucosyluronic acid)bilirubin
Chemical Formula:C45H52N4O18
Weight:Average: 936.921
Monoisotopic: 936.32766085
InChI Key:SCJLWMXOOYZBTH-BTVQFETGSA-N
InChI:InChI=1S/C45H52N4O18/c1-7-20-19(6)40(58)49-27(20)14-25-18(5)23(10-12-31(51)65-45-37(57)33(53)35(55)39(67-45)43(62)63)29(47-25)15-28-22(17(4)24(46-28)13-26-16(3)21(8-2)41(59)48-26)9-11-30(50)64-44-36(56)32(52)34(54)38(66-44)42(60)61/h7-8,13-14,32-39,44-47,52-57H,1-2,9-12,15H2,3-6H3,(H,48,59)(H,49,58)(H,60,61)(H,62,63)/b26-13-,27-14-/t32-,33-,34-,35-,36+,37+,38-,39-,44+,45+/m0/s1
CAS number:17459-92-6
IUPAC Name:(2S,3S,4S,5R,6S)-6-{[3-(2-{[3-(3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-oxopropyl)-5-{[(2E)-3-ethenyl-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2E)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional IUPAC Name:(2S,3S,4S,5R,6S)-6-{[3-(2-{[3-(3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-oxopropyl)-5-{[(2E)-3-ethenyl-5-hydroxy-4-methylpyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2E)-4-ethenyl-5-hydroxy-3-methylpyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES:[H]\C(C1=C(C)C(CCC(=O)O[C@]2([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)=C(CC2=C(CCC(=O)O[C@]3([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]3([H])O)C(C)=C(N2)C(\[H])=C2/N=C(O)C(C)=C2C=C)N1)=C1\N=C(O)C(C=C)=C1C
Chemical Taxonomy
Description belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassBilirubins
Direct ParentBilirubins
Alternative Parents
Substituents
  • Bilirubin skeleton
  • O-glucuronide
  • 1-o-glucuronide
  • Tetracarboxylic acid or derivatives
  • Glucuronic acid or derivatives
  • Beta-hydroxy acid
  • Fatty acid ester
  • Monosaccharide
  • Oxane
  • Pyran
  • Substituted pyrrole
  • Fatty acyl
  • Hydroxy acid
  • Pyrroline
  • Pyrrole
  • Heteroaromatic compound
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Lactam
  • Carboxamide group
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Polyol
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.32ALOGPS
logP-1.7ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
pKa (Strongest Basic)4.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area363.8 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity234.54 m³·mol⁻¹ChemAxon
Polarizability97.04 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Bilirubin diglucuronide + 2 Water + 3 Reduced acceptor <> D-Urobilinogen +2 D-Glucuronic acid +3 Acceptor
SMPDB Pathways:Not Available
KEGG Pathways:
  • Porphyrin and chlorophyll metabolism ec00860
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-0200030903-3f731d3255f730a58952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016u-0300070902-a0595a946705461ddb24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-2200094431-2cedb95f9845511ac143View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-0200025912-c488140c352914da3532View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-2800020923-c9e3902c3b856732b595View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r7-6900003740-e2aa55faca0003c1270fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-0010500539-05ec0afe18cb6d6a4983View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0230530967-386f3f3c90b3b8a6bb6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-3490340563-80e35a547643c4a2b391View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0540-1720170916-65c2b0b7a27f92bc8cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0670-5350061975-523df2bd3cff46ef40a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-5090120520-83d0638c5c3df842db5dView 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:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID18392
HMDB IDHMDB03325
Pubchem Compound ID5459911
Kegg IDC05787
ChemSpider ID4573640
WikipediaBilirubin diglucuronide
BioCyc IDBILIRUBIN-BISGLUCURONOSIDE
EcoCyc IDBILIRUBIN-BISGLUCURONOSIDE

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.

Transporters

Protein Details
1. Glucuronide carrier protein
General function:
Involved in transporter activity
Specific function:
Responsible for the transport of glucuronide into the cell energized by the proton motive force (probably by symport). Import is enhanced by uidC (gusC, AC Q47706)
Gene Name:
uidB
Uniprot ID:
P0CE45
Molecular weight:
49892