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

Details

Stereochemistry ACHIRAL
Molecular Formula C33H36N4O6
Molecular Weight 584.6634
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of BILIRUBIN

SMILES

C=CC/1=C(C)C(=N\C1=C(\[H])/c2c(C)c(CCC(=O)O)c(Cc3c(CCC(=O)O)c(C)c(/C(/[H])=C\4/C(=C(C=C)C(=N4)O)C)[nH]3)[nH]2)O

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

Molecular Formula C33H36N4O6
Molecular Weight 584.6634
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

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
Fixed drug combinations and the displacement of bilirubin from albumin.
1971 Jul
Papillary necrosis in the Gunn rat: rapid induction by analgesics.
1972 Jul
[Interrelation of bilirubin and free fatty acids in newborn infants with pathologic conditions].
1989 Jan
Protection of glutathione S-transferase from bilirubin inhibition.
1989 Jun
[Hepatic veno-occlusive disease associated to the use of azathioprine in a renal transplant recipient].
1996 Dec
New concepts in bilirubin and jaundice: report of the Third International Bilirubin Workshop, April 6-8, 1995, Trieste, Italy.
1996 Nov
Intestinal excretion of unconjugated bilirubin in man and rats with inherited unconjugated hyperbilirubinemia.
1997 Aug
Effect of growth hormone or chromium picolinate on swine metabolism and inflammatory cytokine production after endotoxin challenge exposure.
1997 Jun
Pancreaticoduodenectomy: a 20-year experience in 516 patients.
2004 Jul
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
Importance of serum bile acids determination in adolescents with juvenile hyperbilirubinaemia.
2004 Jun
In vitro protein binding of teicoplanin to neonatal serum.
2004 Oct
Interleukin 1beta inhibits CAR-induced expression of hepatic genes involved in drug and bilirubin clearance.
2004 Oct
Induction of heme oxygenase-1 in human hepatocytes to protect them from ethanol-induced cytotoxicity.
2004 Sep
Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of 3-hydroxydesloratadine.
2004 Sep
Heme oxygenase-2 protects against glutathione depletion-induced neuronal apoptosis mediated by bilirubin and cyclic GMP.
2005 Apr
Transcutaneous bilirubinometry in preterm infants receiving phototherapy.
2005 Apr
Small interference RNA-mediated gene silencing of human biliverdin reductase, but not that of heme oxygenase-1, attenuates arsenite-mediated induction of the oxygenase and increases apoptosis in 293A kidney cells.
2005 Apr 29
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
Identification of human UDP-glucuronosyltransferase isoform(s) responsible for the glucuronidation of 2-(4-chlorophenyl)- 5-(2-furyl)-4-oxazoleacetic acid (TA-1801A).
2005 Jun
Inhibition of rat liver UDP-glucuronosyltransferase by silymarin and the metabolite silibinin-glucuronide.
2005 Jun 24
Dual role of orphan nuclear receptor pregnane X receptor in bilirubin detoxification in mice.
2005 Mar
A multimedia CD-ROM tool to improve student understanding of bile salts and bilirubin metabolism: evaluation of its use in a medical hybrid PBL course.
2005 Mar
Modulation of intestinal transport of 2,4-dinitrophenyl-S-glutathione, a multidrug resistance-associated protein 2 substrate, by bilirubin treatment in rats.
2005 May
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
Gallbladder bile composition in patients with Crohn 's disease.
2006 Jan 7
Heme oxygenase-1 protects tumor cells against photodynamic therapy-mediated cytotoxicity.
2006 Jun 8
Heme oxygenase-1 enhances renal mitochondrial transport carriers and cytochrome C oxidase activity in experimental diabetes.
2006 Jun 9
The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution.
2007 Sep
Carbon monoxide donors or heme oxygenase-1 (HO-1) overexpression blocks interleukin-18-mediated NF-kappaB-PTEN-dependent human cardiac endothelial cell death.
2008 Feb 1
[Portal vein hypertension during azathioprine therapy in patients with Crohn's disease--a frequent phenomenon?].
2008 May
Interaction of porphyrins with human organic anion transporting polypeptide 1B1.
2009 Nov 10
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
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
Importance of UDP-glucuronosyltransferase 1A1 expression in skin and its induction by UVB in neonatal hyperbilirubinemia.
2013 Nov
Epigenetic regulation is a crucial factor in the repression of UGT1A1 expression in the human kidney.
2013 Oct
Mitochondrial targeting of bilirubin regulatory enzymes: An adaptive response to oxidative stress.
2015 Jan 1
Heme-regulated eIF2α kinase plays a crucial role in protecting erythroid cells against Pb-induced hemolytic stress.
2015 Mar 16
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:30:20 UTC 2021
Edited
by admin
on Sat Jun 26 15:30:20 UTC 2021
Record UNII
RFM9X3LJ49
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BILIRUBIN
MI  
Common Name English
NSC-26685
Code English
BILIRUBIN [WHO-DD]
Common Name English
HEMATOIDIN
Common Name English
BILIRUBIN [MI]
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
LOINC 89871-8
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LOINC 35194-0
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LOINC 54362-9
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CFR 21 CFR 862.1110
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LOINC 14421-2
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LOINC 14423-8
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CFR 21 CFR 862.1115
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LOINC 12476-8
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NCI_THESAURUS C304
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LOINC 14422-0
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CFR 21 CFR 862.1113
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LOINC 59828-4
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LOINC 43824-2
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Code System Code Type Description
NCI_THESAURUS
C305
Created by admin on Sat Jun 26 15:30:20 UTC 2021 , Edited by admin on Sat Jun 26 15:30:20 UTC 2021
PRIMARY
MESH
D001663
Created by admin on Sat Jun 26 15:30:20 UTC 2021 , Edited by admin on Sat Jun 26 15:30:20 UTC 2021
PRIMARY
EPA CompTox
635-65-4
Created by admin on Sat Jun 26 15:30:20 UTC 2021 , Edited by admin on Sat Jun 26 15:30:20 UTC 2021
PRIMARY
FDA UNII
RFM9X3LJ49
Created by admin on Sat Jun 26 15:30:20 UTC 2021 , Edited by admin on Sat Jun 26 15:30:20 UTC 2021
PRIMARY
CAS
635-65-4
Created by admin on Sat Jun 26 15:30:20 UTC 2021 , Edited by admin on Sat Jun 26 15:30:20 UTC 2021
PRIMARY
PUBCHEM
5280352
Created by admin on Sat Jun 26 15:30:20 UTC 2021 , Edited by admin on Sat Jun 26 15:30:20 UTC 2021
PRIMARY
MERCK INDEX
M2492
Created by admin on Sat Jun 26 15:30:20 UTC 2021 , Edited by admin on Sat Jun 26 15:30:20 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
BILIRUBIN
Created by admin on Sat Jun 26 15:30:20 UTC 2021 , Edited by admin on Sat Jun 26 15:30:20 UTC 2021
PRIMARY
ECHA (EC/EINECS)
211-239-7
Created by admin on Sat Jun 26 15:30:20 UTC 2021 , Edited by admin on Sat Jun 26 15:30:20 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> SUBSTRATE