Human Metabolome Database Version 3.5

Showing metabocard for Bilirubin diglucuronide (HMDB03325)

Record Information
Version 3.5
Creation Date 2006-07-26 04:28:39 -0600
Update Date 2013-07-24 11:54:31 -0600
HMDB ID HMDB03325
Secondary Accession Numbers
  • HMDB06518
Metabolite Identification
Common Name Bilirubin diglucuronide
Description Bilirubin 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C45H52N4O18
Average Molecular Weight 936.9104
Monoisotopic Molecular Weight 936.32766088
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 Number 17459-92-6
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 Key SCJLWMXOOYZBTH-SDXZDYKGSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Tetrapyrroles and Derivatives
Sub Class Bilirubins
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 Parent Bilirubins
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Waste products
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.13 g/L ALOGPS
LogP 1.32 ALOGPS
LogP -0.78 ChemAxon
LogS -3.87 ALOGPS
pKa (strongest acidic) 2.97 ChemAxon
pKa (strongest basic) -4 ChemAxon
Hydrogen Acceptor Count 16 ChemAxon
Hydrogen Donor Count 12 ChemAxon
Polar Surface Area 356.82 A2 ChemAxon
Rotatable Bond Count 18 ChemAxon
Refractivity 233.49 ChemAxon
Polarizability 94.38 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Name SMPDB Link KEGG Link
Porphyrin Metabolism SMP00024 map00860 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Normal
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Normal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023140
KNApSAcK ID Not Available
Chemspider ID 4573640 Link_out
KEGG Compound ID C05787 Link_out
BioCyc ID BILIRUBIN-BISGLUCURONOSIDE Link_out
BiGG ID 46500 Link_out
Wikipedia Link Bilirubin diglucuronide Link_out
NuGOwiki Link HMDB03325 Link_out
Metagene Link HMDB03325 Link_out
METLIN ID 6883 Link_out
PubChem Compound 5459911 Link_out
PDB ID Not Available
ChEBI ID 18392 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: UDP-glucuronosyltransferase 2B28
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT2B28
Uniprot ID: Q9BY64 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B4
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT2B4
Uniprot ID: P06133 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-4
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT1A4
Uniprot ID: P22310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B10
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT2B10
Uniprot ID: P36537 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B7
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT2B7
Uniprot ID: P16662 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B15
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT2B15
Uniprot ID: P54855 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2A1
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT2A1
Uniprot ID: Q9Y4X1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-1
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT1A1
Uniprot ID: P22309 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-9
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT1A9
Uniprot ID: O60656 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-8
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT1A8
Uniprot ID: Q9HAW9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-3
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT1A3
Uniprot ID: P35503 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-10
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT1A10
Uniprot ID: Q9HAW8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B17
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT2B17
Uniprot ID: O75795 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-6
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT1A6
Uniprot ID: P19224 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-5
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT1A5
Uniprot ID: P35504 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B11
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT2B11
Uniprot ID: O75310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-7
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT1A7
Uniprot ID: Q9HAW7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-glucuronidase
Reactions:
Bilirubin diglucuronide + Water + Reduced acceptor unknown D-Urobilinogen + D-Glucuronic acid + Acceptor details
Gene Name: GUSB
Uniprot ID: P08236 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2A3
Reactions:
Uridine diphosphate glucuronic acid + Bilirubin unknown Uridine 5'-diphosphate + Bilirubin diglucuronide details
Gene Name: UGT2A3
Uniprot ID: Q6UWM9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: HCG2039726, isoform CRA_f
Reactions: Not Available
Gene Name: UGT1A10
Uniprot ID: Q5DT02 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: HCG2039726, isoform CRA_e
Reactions: Not Available
Gene Name: UGT1A8
Uniprot ID: Q5DSZ6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP glycosyltransferase 1 family polypeptide A7
Reactions: Not Available
Gene Name: UGT1A7
Uniprot ID: Q5DSZ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA