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Record Information
Version3.6
Creation Date2006-07-26 10:28:39 UTC
Update Date2017-08-16 04:07:43 UTC
HMDB IDHMDB0003325
Secondary Accession Numbers
  • HMDB03325
  • 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
SynonymsNot Available
Chemical FormulaC45H52N4O18
Average Molecular Weight936.921
Monoisotopic Molecular Weight936.32766085
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 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
CAS Registry Number17459-92-6
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
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-GIDSPALLSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
StatusExpected but 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 mg/mLALOGPS
logP1.62ALOGPS
logP-1.7ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
pKa (Strongest Basic)4.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area363.8 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity234.54 m3·mol-1ChemAxon
Polarizability97.17 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Acute Intermittent PorphyriaSMP00344Not Available
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseSMP00345Not Available
Hereditary Coproporphyria (HCP)SMP00342Not Available
Porphyria Variegata (PV)SMP00346Not Available
Porphyrin MetabolismSMP00024map00860
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      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 LinkHMDB0003325
      METLIN ID6883
      PubChem Compound5459911
      PDB IDNot Available
      ChEBI ID18392
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Download (PDF)
      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

      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
      Gene Name:
      UGT2B28
      Uniprot ID:
      Q9BY64
      Molecular weight:
      38742.9
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
      Gene Name:
      UGT2B4
      Uniprot ID:
      P06133
      Molecular weight:
      60512.035
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
      Gene Name:
      UGT1A4
      Uniprot ID:
      P22310
      Molecular weight:
      60024.535
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      References
      1. Meunier CJ, Verbeeck RK: Glucuronidation of R- and S-ketoprofen, acetaminophen, and diflunisal by liver microsomes of adjuvant-induced arthritic rats. Drug Metab Dispos. 1999 Jan;27(1):26-31. [PubMed:9884306 ]
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT2B10
      Uniprot ID:
      P36537
      Molecular weight:
      60773.485
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
      Gene Name:
      UGT2B7
      Uniprot ID:
      P16662
      Molecular weight:
      60720.15
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
      Gene Name:
      UGT2B15
      Uniprot ID:
      P54855
      Molecular weight:
      61035.815
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
      Gene Name:
      UGT2A1
      Uniprot ID:
      Q9Y4X1
      Molecular weight:
      60771.605
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
      Gene Name:
      UGT1A1
      Uniprot ID:
      P22309
      Molecular weight:
      59590.91
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      References
      1. Meunier CJ, Verbeeck RK: Glucuronidation of R- and S-ketoprofen, acetaminophen, and diflunisal by liver microsomes of adjuvant-induced arthritic rats. Drug Metab Dispos. 1999 Jan;27(1):26-31. [PubMed:9884306 ]
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
      Gene Name:
      UGT1A9
      Uniprot ID:
      O60656
      Molecular weight:
      59940.495
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A8
      Uniprot ID:
      Q9HAW9
      Molecular weight:
      59741.035
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A3
      Uniprot ID:
      P35503
      Molecular weight:
      60337.835
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A10
      Uniprot ID:
      Q9HAW8
      Molecular weight:
      59809.075
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
      Gene Name:
      UGT2B17
      Uniprot ID:
      O75795
      Molecular weight:
      61094.915
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
      Gene Name:
      UGT1A6
      Uniprot ID:
      P19224
      Molecular weight:
      60750.215
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A5
      Uniprot ID:
      P35504
      Molecular weight:
      60070.565
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT2B11
      Uniprot ID:
      O75310
      Molecular weight:
      61037.8
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A7
      Uniprot ID:
      Q9HAW7
      Molecular weight:
      59818.315
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
      Specific function:
      Plays an important role in the degradation of dermatan and keratan sulfates.
      Gene Name:
      GUSB
      Uniprot ID:
      P08236
      Molecular weight:
      74731.46
      Reactions
      Bilirubin diglucuronide + Water + Reduced acceptor → D-Urobilinogen + D-Glucuronic acid + Acceptordetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds (By similarity).
      Gene Name:
      UGT2A3
      Uniprot ID:
      Q6UWM9
      Molecular weight:
      60253.94
      Reactions
      Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      Not Available
      Gene Name:
      UGT1A10
      Uniprot ID:
      Q5DT02
      Molecular weight:
      59809.1
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      Not Available
      Gene Name:
      UGT1A8
      Uniprot ID:
      Q5DSZ6
      Molecular weight:
      59741.0
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      Not Available
      Gene Name:
      UGT1A7
      Uniprot ID:
      Q5DSZ7
      Molecular weight:
      59818.3