Record Information
Version3.6
Creation Date2006-07-26 10:28:39 UTC
Update Date2013-07-24 17:54:31 UTC
HMDB IDHMDB03325
Secondary Accession Numbers
  • HMDB06518
Metabolite Identification
Common NameBilirubin diglucuronide
DescriptionBilirubin diglucuronide is a water soluble version of bilirubin. Conversion of bilirubin IX-alpha to a water-soluble form by disruption of the hydrogen bonds is essential for elimination by the liver and kidney. This is achieved by glucuronic acid conjugation of the propionic acid side chains of bilirubin. Bilirubin glucuronides are water-soluble and are readily excreted in bile. Bilirubin is primarily excreted in normal human bile as diglucuronide; unconjugated bilirubin accounts for only 1-4% of pigments in normal bile.
Structure
Thumb
Synonyms
  1. (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
  2. (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
  3. Bilirubin beta-diglucuronide
  4. Bilirubin-bisglucuronoside
  5. Bis(glucosyluronic acid)bilirubin
Chemical FormulaC45H52N4O18
Average Molecular Weight936.9104
Monoisotopic Molecular Weight936.32766088
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-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-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-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]m
CAS Registry Number17459-92-6
SMILES
CC1=C(C=C)\C(NC1=O)=C/C1=C(C)C(CCC(=O)O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)=C(CC2=C(CCC(=O)O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C(C)=C(N2)\C=C2\NC(=O)C(C=C)=C2C)N1
InChI Identifier
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
InChI KeySCJLWMXOOYZBTH-SDXZDYKGSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassTetrapyrroles and Derivatives
Sub ClassBilirubins
Other Descriptors
  • Organic Compounds
Substituents
  • 1,2 Diol
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Dipyrrin
  • Fatty Acid Ester
  • Glucuronic Acid Or Derivative
  • Glucuronide
  • Glycosyl Compound
  • Hexose Disaccharide
  • O Glycosyl Compound
  • Oxane
  • Pyrrole
  • Saccharide
  • Secondary Alcohol
  • Sugar Acid
Direct ParentBilirubins
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.13 g/LALOGPS
logP1.32ALOGPS
logP-0.78ChemAxon
logS-3.9ALOGPS
pKa (strongest acidic)2.97ChemAxon
pKa (strongest basic)-4ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count16ChemAxon
hydrogen donor count12ChemAxon
polar surface area356.82ChemAxon
rotatable bond count18ChemAxon
refractivity233.49ChemAxon
polarizability94.38ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Porphyrin MetabolismSMP00024map00860
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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 IDFDB023140
KNApSAcK IDNot Available
Chemspider ID4573640
KEGG Compound IDC05787
BioCyc IDBILIRUBIN-BISGLUCURONOSIDE
BiGG ID46500
Wikipedia LinkBilirubin diglucuronide
NuGOwiki LinkHMDB03325
Metagene LinkHMDB03325
METLIN ID6883
PubChem Compound5459911
PDB IDNot Available
ChEBI ID18392
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Luo J, Lim CK: Isolation and characterization of new porphyrin metabolites in human porphyria cutanea tarda and in rats treated with hexachlorobenzene by HPTLC, HPLC and liquid secondary ion mass spectrometry. Biomed Chromatogr. 1995 May-Jun;9(3):113-22. Pubmed: 7655298
  2. Mshelia DS, Buba AA: Point of care testing: a delight or a dilemma in the developing world?: an overview. Niger Postgrad Med J. 2005 Jun;12(2):136-9. Pubmed: 15997265
  3. Fevery J, Blanckaert N, Leroy P, Michiels R, Heirwegh KP: Analysis of bilirubins in biological fluids by extraction and thin-layer chromatography of the intact tetrapyrroles: application to bile of patients with Gilbert's syndrome, hemolysis, or cholelithiasis. Hepatology. 1983 Mar-Apr;3(2):177-83. Pubmed: 6832709
  4. Chowdhury JR, Chowdhury NR, Wu G, Shouval R, Arias IM: Bilirubin mono- and diglucuronide formation by human liver in vitro: assay by high-pressure liquid chromatography. Hepatology. 1981 Nov-Dec;1(6):622-7. Pubmed: 6796486
  5. Goresky CA, Gordon ER, Hinchey EJ, Fried GM: Bilirubin conjugate changes in the bile of gallbladders containing gallstones. Hepatology. 1995 Feb;21(2):373-82. Pubmed: 7843708

Enzymes

Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT2B4
Uniprot ID:
P06133
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT1A4
Uniprot ID:
P22310
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT2B10
Uniprot ID:
P36537
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT2B7
Uniprot ID:
P16662
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT2B15
Uniprot ID:
P54855
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT1A1
Uniprot ID:
P22309
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT1A9
Uniprot ID:
O60656
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT1A3
Uniprot ID:
P35503
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT1A10
Uniprot ID:
Q9HAW8
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT2B17
Uniprot ID:
O75795
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT1A6
Uniprot ID:
P19224
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT1A5
Uniprot ID:
P35504
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT2B11
Uniprot ID:
O75310
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT1A7
Uniprot ID:
Q9HAW7
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
GUSB
Uniprot ID:
P08236
Reactions
Bilirubin diglucuronide + Water + Reduced acceptor unknown D-Urobilinogen + D-Glucuronic acid + Acceptordetails
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Reactions
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6