Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-09-15 17:15:14 UTC
Update Date2021-09-14 15:43:35 UTC
HMDB IDHMDB0010332
Secondary Accession Numbers
  • HMDB10332
Metabolite Identification
Common NameBilirubin glucuronide
DescriptionBilirubin glucuronide belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Bilirubin glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). The reaction is a transfer of two glucuronic acid groups including UDP glucuronic acid sequentially to the propionic acid groups of the bilirubin, primarily catalyzed by UGT1A1. Furthermore, those affected may develop kernicterus (deposits of pigment in the brain) that can cause nerve degeneration. Note that biliary duct blockage can also lead to conjugated hyperbilirubinemia but the pathophysiology is that backflow of bilirubin di-glucuronide with little indirect bilirubin and bilirubin glucuronide from bile duct through liver into blood plasma. Normally, there is just a little conjugated bilirubin escapes into the general circulation.
Structure
Data?1582752815
Synonyms
ValueSource
2,17-Diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoateHMDB
2,17-Diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acidHMDB
2,17-Diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid mono-beta-D-glucopyranuronosyl esterHMDB
2,17-Diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid mono-beta-delta-glucopyranuronosyl esterHMDB
Bilirubin glucuronateHMDB
Bilirubin glucuronic acid conjugatesHMDB
Bilirubin monoglucuronideHMDB
Glucuronic acid conjugates OF bilirubinHMDB
mono-beta-delta-Glucopyranuronosyl ester 2,17-diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoateHMDB
mono-beta-delta-Glucopyranuronosyl ester 2,17-diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acidHMDB
(2S,3S,4S,5R,6R)-5-{[3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,6-trihydroxyoxane-2-carboxylateHMDB
Glucuronate conjugates OF bilirubinHMDB
Chemical FormulaC39H44N4O12
Average Molecular Weight760.7863
Monoisotopic Molecular Weight760.295572892
IUPAC Name(2S,3S,4S,5R,6R)-5-{[3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,6-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-5-{[3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,6-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(=O)O[C@H]3[C@H](O)O[C@@H]([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/C39H44N4O12/c1-7-20-19(6)36(49)43-27(20)14-25-17(4)22(9-11-30(44)45)28(41-25)15-29-23(18(5)24(40-29)13-26-16(3)21(8-2)37(50)42-26)10-12-31(46)54-35-33(48)32(47)34(38(51)52)55-39(35)53/h7-8,13-14,32-35,39-41,47-48,53H,1-2,9-12,15H2,3-6H3,(H,42,50)(H,43,49)(H,44,45)(H,51,52)/b26-13-,27-14-/t32-,33-,34-,35+,39+/m0/s1
InChI KeyNCZCFMOVDHRJII-VBORGTJOSA-N
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
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Fatty acid ester
  • Monosaccharide
  • Hydroxy acid
  • Oxane
  • Fatty acyl
  • Substituted pyrrole
  • Pyran
  • Heteroaromatic compound
  • Pyrrole
  • Pyrroline
  • Secondary carboxylic acid amide
  • Hemiacetal
  • Lactam
  • Carboxylic acid ester
  • 1,2-diol
  • Carboxamide group
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP2.51ALOGPS
logP1.17ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area260.6 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity201.19 m³·mol⁻¹ChemAxon
Polarizability81.72 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+270.40530932474
DeepCCS[M-H]-268.66230932474
DeepCCS[M-2H]-302.69530932474
DeepCCS[M+Na]+276.6530932474
AllCCS[M+H]+268.032859911
AllCCS[M+H-H2O]+267.432859911
AllCCS[M+NH4]+268.732859911
AllCCS[M+Na]+268.832859911
AllCCS[M-H]-269.932859911
AllCCS[M+Na-2H]-274.932859911
AllCCS[M+HCOO]-280.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Bilirubin glucuronideCC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(=O)O[C@H]3[C@H](O)O[C@@H]([C@@H](O)[C@@H]3O)C(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N18459.9Standard polar33892256
Bilirubin glucuronideCC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(=O)O[C@H]3[C@H](O)O[C@@H]([C@@H](O)[C@@H]3O)C(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N13870.6Standard non polar33892256
Bilirubin glucuronideCC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(=O)O[C@H]3[C@H](O)O[C@@H]([C@@H](O)[C@@H]3O)C(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N17102.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 10V, Positive-QTOFsplash10-002f-0300030900-0865b86b083bbe063f3b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 20V, Positive-QTOFsplash10-00os-0900150700-a3d05b0eb0cb1285c3432017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 40V, Positive-QTOFsplash10-004j-3900134200-ca8293fb4addf5c11e9e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 10V, Negative-QTOFsplash10-067l-2400044900-10373cf294707957940e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 20V, Negative-QTOFsplash10-00lu-4700091400-55082bd1b554e6e72fad2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 40V, Negative-QTOFsplash10-05o0-6300090000-9b0c34749943f4dd7f982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 10V, Negative-QTOFsplash10-057i-9100077600-20e650c74f102f68001c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 20V, Negative-QTOFsplash10-053l-7300097300-9da993c164d046106b502021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 40V, Negative-QTOFsplash10-000l-5090671000-d3c50eb55fd5219cae712021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 10V, Positive-QTOFsplash10-01ox-0010120900-f4caa7fa954314bd2ce32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 20V, Positive-QTOFsplash10-02tc-0010332900-c5e0d05638e77b1c92c02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilirubin glucuronide 40V, Positive-QTOFsplash10-0v0r-0895346200-dcb90c3f6d2d07f63a122021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027484
KNApSAcK IDNot Available
Chemspider ID4942827
KEGG Compound IDC03033
BioCyc IDBeta-D-Glucuronides
BiGG ID41733
Wikipedia LinkBilirubin glucuronide
METLIN IDNot Available
PubChem Compound6438344
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 18 proteins in total.

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
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
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
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. 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
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
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
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
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
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
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

Only showing the first 10 proteins. There are 18 proteins in total.