U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C33H36N4O6
Molecular Weight 584.6621
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of BILIRUBIN

SMILES

CC1=C(C=C)\C(NC1=O)=C\C2=C(C)C(CCC(O)=O)=C(CC3=C(CCC(O)=O)C(C)=C(N3)\C=C4/NC(=O)C(C=C)=C4C)N2

InChI

InChIKey=BPYKTIZUTYGOLE-IFADSCNNSA-N
InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-

HIDE SMILES / InChI
Bilirubin is an orange-yellow pigment made during the normal breakdown of red blood cells. Bilirubin passes through the liver and is excreted out of the body. Occasionally, higher bilirubin levels may indicate an increased rate of destruction of red blood cells (hemolysis). A high level of bilirubin in the blood is called hyperbilirubinemia. High bilirubin levels can cause jaundice. Jaundice makes the skin and the whites of the eyes appear yellow, due to the brown and yellow bilirubin in the blood. Phototherapy for neonatal is one of the treatment methods against hyperbilirubinemia. Light absorption by bilirubin in the skin transforms the native Z,Z-bilirubin to conformational photoisomers Z,E-bilirubin and E,Z-bilirubin and structural photoisomers E,Z-lumirubin and E,E-lumirubin. Formation and excretion of Z,E-bilirubin and E,Z-lumirubin are both important routes of elimination of bilirubin through bile and urine, although the precise contributions of the various photoisomers to the overall elimination of bilirubin are still unknown.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Interrelation of bilirubin and free fatty acids in newborn infants with pathologic conditions].
1989 Jan
[Apolipoprotein A in patients with alcoholic liver disease].
1990 Mar-Apr
[Hepatic veno-occlusive disease associated to the use of azathioprine in a renal transplant recipient].
1996 Dec
Intestinal excretion of unconjugated bilirubin in man and rats with inherited unconjugated hyperbilirubinemia.
1997 Aug
Haemolytic anaemia due to metformin.
2000 Feb
Synergistic role of 3-hydroxy-3-methylglutaryl coenzyme A reductase and cholesterol 7alpha-hydroxylase in the pathogenesis of manganese-bilirubin-induced cholestasis in rats.
2003 Jun
Hepatitis C virus infection as a likely etiology of intrahepatic cholangiocarcinoma.
2004 Jul
Heme oxygenase-1 inhibits angiotensin II-induced cardiac hypertrophy in vitro and in vivo.
2004 Jul 20
Interleukin 1beta inhibits CAR-induced expression of hepatic genes involved in drug and bilirubin clearance.
2004 Oct
Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of 3-hydroxydesloratadine.
2004 Sep
Goal-directed therapy of cardiac preload in induced whole-body hyperthermia.
2005 Aug
Role of microtubules in estradiol-17beta-D-glucuronide-induced alteration of canalicular Mrp2 localization and activity.
2005 Feb
In vivo spectroscopy of jaundiced newborn skin reveals more than a bilirubin index.
2005 Jan
Impaired expression of hepatic multidrug resistance protein 2 is associated with posthepatectomy hyperbilirubinemia in patients with biliary cancer.
2005 Sep
Cryopreserved fetal liver cell transplants support the chronic failing liver in rats with CCl4-induced cirrhosis.
2006
Heme oxygenase-1 enhances renal mitochondrial transport carriers and cytochrome C oxidase activity in experimental diabetes.
2006 Jun 9
Glutamate induces oxidative stress and apoptosis in cerebral vascular endothelial cells: contributions of HO-1 and HO-2 to cytoprotection.
2006 May
Characterization of the UDP glucuronosyltransferase activity of human liver microsomes genotyped for the UGT1A1*28 polymorphism.
2007 Dec
Protective response of the Ah receptor to ANIT-induced biliary epithelial cell toxicity in see-through medaka.
2008 Apr
Global changes in gene regulation demonstrate that unconjugated bilirubin is able to upregulate and activate select components of the endoplasmic reticulum stress response pathway.
2010 Mar-Apr
Adiponectin-mediated heme oxygenase-1 induction protects against iron-induced liver injury via a PPARα dependent mechanism.
2010 Oct
Functional induction of the cystine-glutamate exchanger system Xc(-) activity in SH-SY5Y cells by unconjugated bilirubin.
2011
In vitro inhibition of heme oxygenase isoenzymes by metalloporphyrins.
2011 Apr
Urinary excretion of bilirubin oxidative metabolites in arsenite-treated mice.
2012
Prevention of paraquat-induced apoptosis in human neuronal SH-SY5Y cells by lipocalin-type prostaglandin D synthase.
2012 Jan
Reduced expression of UGT1A1 in intestines of humanized UGT1 mice via inactivation of NF-κB leads to hyperbilirubinemia.
2012 Jan
Metabolism of bilirubin by human cytochrome P450 2A6.
2012 May 15
Heme and heme biosynthesis intermediates induce heme oxygenase-1 and cytochrome P450 2A5, enzymes with putative sequential roles in heme and bilirubin metabolism: different requirement for transcription factor nuclear factor erythroid- derived 2-like 2.
2012 Nov
Cyclosporine A treated in vitro models induce cholestasis response through comparison of phenotype-directed gene expression analysis of in vivo Cyclosporine A-induced cholestasis.
2013 Aug 29
Cytochrome P450 2A5 and bilirubin: mechanisms of gene regulation and cytoprotection.
2013 Jul 15
Epigenetic regulation is a crucial factor in the repression of UGT1A1 expression in the human kidney.
2013 Oct
Physiological concentrations of unconjugated bilirubin prevent oxidative stress-induced hepatocanalicular dysfunction and cholestasis.
2014 Feb
Characterization of the zebrafish Ugt repertoire reveals a new class of drug-metabolizing UDP glucuronosyltransferases.
2014 Jul
Mitochondrial targeting of bilirubin regulatory enzymes: An adaptive response to oxidative stress.
2015 Jan 1
Patents
Name Type Language
BILIRUBIN
MI  
Common Name English
NSC-26685
Code English
HEMATOIDIN
Common Name English
BILIRUBIN [MI]
Common Name English
Bilirubin [WHO-DD]
Common Name English
BILIRUBIN IX.ALPHA.
Common Name English
(4Z,15Z)-BILIRUBIN IX.ALPHA.
Common Name English
BILIRUBIN TEST [VANDF]
Common Name English
1,3,6,7-TETRAMETHYL-4,5-DICARBOXYETHYL-2,8-DIVINYL-(B-13)-DIHYDROBILENONE
Common Name English
2,17-DIETHENYL-1,10,19,22,23,24-HEXAHYDRO-3,7,13,18-TETRAMETHYL-1,19-DIOXO-21H-BILINE-8,12-DIPROPANOIC ACID
Systematic Name English
1,10,19,22,23,24-HEXAHYDRO-2,7,13,17-TETRAMETHYL-1,19-DIOXO-3,18-DIVINYLBILINE-8,12-DIPROPIONIC ACID
Systematic Name English
CHOLERYTHRIN
Common Name English
Classification Tree Code System Code
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Code System Code Type Description
NCI_THESAURUS
C305
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PRIMARY
MESH
D001663
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PRIMARY
EPA CompTox
DTXSID8060905
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PRIMARY
FDA UNII
RFM9X3LJ49
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PRIMARY
CAS
635-65-4
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PRIMARY
PUBCHEM
5280352
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PRIMARY
CHEBI
16990
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PRIMARY
DAILYMED
RFM9X3LJ49
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PRIMARY
NSC
26685
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PRIMARY
MERCK INDEX
m2492
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PRIMARY Merck Index
WIKIPEDIA
BILIRUBIN
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PRIMARY
ECHA (EC/EINECS)
211-239-7
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PRIMARY