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Human Metabolome Database Version 3.5

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Showing metabocard for Bilirubin diglucuronide (HMDB03325)

Record Information
Version 3.5
Creation Date 2006-07-26 04:28:39 -0600
Update Date 2013-02-08 17:12:26 -0700
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 | 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 Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Porphyrin Metabolism SMP00024 map00860 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank 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:
    Gene Name: UGT2B28
    Uniprot ID: Q9BY64 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B4
    Reactions:
      Gene Name: UGT2B4
      Uniprot ID: P06133 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 1-4
      Reactions:
        Gene Name: UGT1A4
        Uniprot ID: P22310 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 2B7
        Reactions:
          Gene Name: UGT2B7
          Uniprot ID: P16662 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: UDP-glucuronosyltransferase 2B15
          Reactions:
            Gene Name: UGT2B15
            Uniprot ID: P54855 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 2A1
            Reactions:
              Gene Name: UGT2A1
              Uniprot ID: Q9Y4X1 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: UDP-glucuronosyltransferase 1-1
              Reactions:
                Gene Name: UGT1A1
                Uniprot ID: P22309 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: UDP-glucuronosyltransferase 1-9
                Reactions:
                  Gene Name: UGT1A9
                  Uniprot ID: O60656 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: UDP-glucuronosyltransferase 1-3
                  Reactions:
                    Gene Name: UGT1A3
                    Uniprot ID: P35503 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: UDP-glucuronosyltransferase 2B17
                    Reactions:
                      Gene Name: UGT2B17
                      Uniprot ID: O75795 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: UDP-glucuronosyltransferase 1-6
                      Reactions:
                        Gene Name: UGT1A6
                        Uniprot ID: P19224 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: UDP-glucuronosyltransferase 1-5
                        Reactions:
                          Gene Name: UGT1A5
                          Uniprot ID: P35504 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: UDP-glucuronosyltransferase 2B11
                          Reactions:
                            Gene Name: UGT2B11
                            Uniprot ID: O75310 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: Beta-glucuronidase
                            Reactions:
                              Gene Name: GUSB
                              Uniprot ID: P08236 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA
                              Name: UDP-glucuronosyltransferase 2A3
                              Reactions:
                                Gene Name: UGT2A3
                                Uniprot ID: Q6UWM9 Link_out
                                Protein Sequence: FASTA
                                Gene Sequence: FASTA
                                Name: HCG2039726, isoform CRA_f
                                Reactions:
                                  Gene Name: UGT1A10
                                  Uniprot ID: Q5DT02 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: HCG2039726, isoform CRA_e
                                  Reactions:
                                    Gene Name: UGT1A8
                                    Uniprot ID: Q5DSZ6 Link_out
                                    Protein Sequence: FASTA
                                    Gene Sequence: FASTA
                                    Name: UDP glycosyltransferase 1 family polypeptide A7
                                    Reactions:
                                      Gene Name: UGT1A7
                                      Uniprot ID: Q5DSZ7 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA