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

Molecular Formula C33H36N4O6
Molecular Weight 584.6621
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
[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
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
[The influence of the dose, time since ingestion and concentration of the xenobiotic on the clinical state and severity of liver damage with patients intoxicated with paracetamol].
2005
Heme oxygenase-2 protects against glutathione depletion-induced neuronal apoptosis mediated by bilirubin and cyclic GMP.
2005 Apr
Evidence for induced microsomal bilirubin degradation by cytochrome P450 2A5.
2005 Nov 15
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
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
The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution.
2007 Sep
Protective response of the Ah receptor to ANIT-induced biliary epithelial cell toxicity in see-through medaka.
2008 Apr
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
Protective effects of bilirubin against cyclophosphamide induced hemorrhagic cystitis in rats.
2008 Mar
[Portal vein hypertension during azathioprine therapy in patients with Crohn's disease--a frequent phenomenon?].
2008 May
Predictive factors associated with the progression to hepatic failure caused by lamivudine-resistant HBV.
2008 Nov
Role of vitamin C transporters and biliverdin reductase in the dual pro-oxidant and anti-oxidant effect of biliary compounds on the placental-fetal unit in cholestasis during pregnancy.
2008 Oct 15
Interaction of porphyrins with human organic anion transporting polypeptide 1B1.
2009 Nov 10
Diagnostic performance of traditional hepatobiliary biomarkers of drug-induced liver injury in the rat.
2010 Aug
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
Differential oxidative stress responses to D-galactosamine-lipopolysaccharide hepatotoxicity based on real time PCR analysis of selected oxidant/antioxidant and apoptotic gene expressions in rat.
2011
In vitro inhibition of heme oxygenase isoenzymes by metalloporphyrins.
2011 Apr
Displacement of bilirubin from albumin in plasma from jaundiced newborns. An in vitro study of purified Chinese herbal constituents and sulfisoxazole.
2011 Jul
Inducible bilirubin oxidase: a novel function for the mouse cytochrome P450 2A5.
2011 Nov 15
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 Channel Opener Diazoxide Attenuates Hypoxia-Induced sFlt-1 Release in Human Choriocarcinoma Cells.
2014 Apr
Physiological concentrations of unconjugated bilirubin prevent oxidative stress-induced hepatocanalicular dysfunction and cholestasis.
2014 Feb
Developmental onset of bilirubin-induced neurotoxicity involves Toll-like receptor 2-dependent signaling in humanized UDP-glucuronosyltransferase1 mice.
2014 Feb 21
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
Heme-regulated eIF2α kinase plays a crucial role in protecting erythroid cells against Pb-induced hemolytic stress.
2015 Mar 16
Role of brain cytochrome P450 mono-oxygenases in bilirubin oxidation-specific induction and activity.
2016 Feb
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:11:07 GMT 2023
Edited
by admin
on Fri Dec 15 15:11:07 GMT 2023
Record UNII
RFM9X3LJ49
Record Status Validated (UNII)
Record Version
  • Download
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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NCI_THESAURUS C304
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CFR 21 CFR 862.1113
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Code System Code Type Description
NCI_THESAURUS
C305
Created by admin on Fri Dec 15 15:11:07 GMT 2023 , Edited by admin on Fri Dec 15 15:11:07 GMT 2023
PRIMARY
MESH
D001663
Created by admin on Fri Dec 15 15:11:07 GMT 2023 , Edited by admin on Fri Dec 15 15:11:07 GMT 2023
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
Created by admin on Fri Dec 15 15:11:07 GMT 2023 , Edited by admin on Fri Dec 15 15:11:07 GMT 2023
PRIMARY
ECHA (EC/EINECS)
211-239-7
Created by admin on Fri Dec 15 15:11:07 GMT 2023 , Edited by admin on Fri Dec 15 15:11:07 GMT 2023
PRIMARY
Related Record Type Details
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