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
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-
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
Title | Date | PubMed |
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[Interrelation of bilirubin and free fatty acids in newborn infants with pathologic conditions]. | 1989 Jan |
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[Apolipoprotein A in patients with alcoholic liver disease]. | 1990 Mar-Apr |
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[Hepatic veno-occlusive disease associated to the use of azathioprine in a renal transplant recipient]. | 1996 Dec |
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Intestinal excretion of unconjugated bilirubin in man and rats with inherited unconjugated hyperbilirubinemia. | 1997 Aug |
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Haemolytic anaemia due to metformin. | 2000 Feb |
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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 |
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Hepatitis C virus infection as a likely etiology of intrahepatic cholangiocarcinoma. | 2004 Jul |
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Heme oxygenase-1 inhibits angiotensin II-induced cardiac hypertrophy in vitro and in vivo. | 2004 Jul 20 |
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Interleukin 1beta inhibits CAR-induced expression of hepatic genes involved in drug and bilirubin clearance. | 2004 Oct |
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Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of 3-hydroxydesloratadine. | 2004 Sep |
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Goal-directed therapy of cardiac preload in induced whole-body hyperthermia. | 2005 Aug |
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Role of microtubules in estradiol-17beta-D-glucuronide-induced alteration of canalicular Mrp2 localization and activity. | 2005 Feb |
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In vivo spectroscopy of jaundiced newborn skin reveals more than a bilirubin index. | 2005 Jan |
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Impaired expression of hepatic multidrug resistance protein 2 is associated with posthepatectomy hyperbilirubinemia in patients with biliary cancer. | 2005 Sep |
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Cryopreserved fetal liver cell transplants support the chronic failing liver in rats with CCl4-induced cirrhosis. | 2006 |
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Heme oxygenase-1 enhances renal mitochondrial transport carriers and cytochrome C oxidase activity in experimental diabetes. | 2006 Jun 9 |
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Glutamate induces oxidative stress and apoptosis in cerebral vascular endothelial cells: contributions of HO-1 and HO-2 to cytoprotection. | 2006 May |
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Characterization of the UDP glucuronosyltransferase activity of human liver microsomes genotyped for the UGT1A1*28 polymorphism. | 2007 Dec |
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Protective response of the Ah receptor to ANIT-induced biliary epithelial cell toxicity in see-through medaka. | 2008 Apr |
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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 |
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Adiponectin-mediated heme oxygenase-1 induction protects against iron-induced liver injury via a PPARα dependent mechanism. | 2010 Oct |
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Functional induction of the cystine-glutamate exchanger system Xc(-) activity in SH-SY5Y cells by unconjugated bilirubin. | 2011 |
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In vitro inhibition of heme oxygenase isoenzymes by metalloporphyrins. | 2011 Apr |
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Urinary excretion of bilirubin oxidative metabolites in arsenite-treated mice. | 2012 |
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Prevention of paraquat-induced apoptosis in human neuronal SH-SY5Y cells by lipocalin-type prostaglandin D synthase. | 2012 Jan |
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Reduced expression of UGT1A1 in intestines of humanized UGT1 mice via inactivation of NF-κB leads to hyperbilirubinemia. | 2012 Jan |
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Metabolism of bilirubin by human cytochrome P450 2A6. | 2012 May 15 |
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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 |
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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 |
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Cytochrome P450 2A5 and bilirubin: mechanisms of gene regulation and cytoprotection. | 2013 Jul 15 |
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Epigenetic regulation is a crucial factor in the repression of UGT1A1 expression in the human kidney. | 2013 Oct |
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Physiological concentrations of unconjugated bilirubin prevent oxidative stress-induced hepatocanalicular dysfunction and cholestasis. | 2014 Feb |
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Characterization of the zebrafish Ugt repertoire reveals a new class of drug-metabolizing UDP glucuronosyltransferases. | 2014 Jul |
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Mitochondrial targeting of bilirubin regulatory enzymes: An adaptive response to oxidative stress. | 2015 Jan 1 |
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BILIRUBIN
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211-239-7
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METABOLITE (PARENT)
METABOLITE (PARENT)
SUBSTANCE RECORD