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
[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
Long-term extracorporeal bilirubin elimination: A case report on cascade resin plasmaperfusion.
1998
Haemolytic anaemia due to metformin.
2000 Feb
Portal hypertension in the presence of minimal liver damage in Crohn's disease on long-term azathioprine: possible endothelial cell injury.
2000 May
Induction of UDP-glucuronosyltransferase UGT1A1 by the flavonoid chrysin in the human hepatoma cell line hep G2.
2000 Sep
Effects on extrahepatic UDP-glucuronosyltransferases in hypophysectomized rat.
2002 Aug
Radixin deficiency causes conjugated hyperbilirubinemia with loss of Mrp2 from bile canalicular membranes.
2002 Jul
[Clinical manifestation and ultrasonic characteristics of five patients with acute arsenic poisoning].
2003 Dec
Heme oxygenase inhibits human airway smooth muscle proliferation via a bilirubin-dependent modulation of ERK1/2 phosphorylation.
2003 Jul 18
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
Nonviral gene transfer into liver and muscle for treatment of hyperbilirubinemia in the gunn rat.
2004 Dec
Pancreaticoduodenectomy: a 20-year experience in 516 patients.
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
Transcutaneous bilirubin measurements and serum total bilirubin levels in indigenous African infants.
2004 Jun
[Decreased peripheral nerve conduction velocity may be associated with lower-serum level of vitamin E in patients with infantile hepatitis syndrome].
2004 May
On the origin of amniotic fluid bilirubin.
2004 May
Interleukin 1beta inhibits CAR-induced expression of hepatic genes involved in drug and bilirubin clearance.
2004 Oct
The human multidrug-resistance-associated protein MRP1 mediates ATP-dependent transport of unconjugated bilirubin.
2004 Oct 15
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
Role of microtubules in estradiol-17beta-D-glucuronide-induced alteration of canalicular Mrp2 localization and activity.
2005 Feb
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
Transcriptional regulation of human UGT1A1 gene expression: activated glucocorticoid receptor enhances constitutive androstane receptor/pregnane X receptor-mediated UDP-glucuronosyltransferase 1A1 regulation with glucocorticoid receptor-interacting protein 1.
2005 Mar
Impaired expression of hepatic multidrug resistance protein 2 is associated with posthepatectomy hyperbilirubinemia in patients with biliary cancer.
2005 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
Protective effects of bilirubin against cyclophosphamide induced hemorrhagic cystitis in rats.
2008 Mar
Predictive factors associated with the progression to hepatic failure caused by lamivudine-resistant HBV.
2008 Nov
Functional induction of the cystine-glutamate exchanger system Xc(-) activity in SH-SY5Y cells by unconjugated bilirubin.
2011
Reduced expression of UGT1A1 in intestines of humanized UGT1 mice via inactivation of NF-κB leads to hyperbilirubinemia.
2012 Jan
Importance of UDP-glucuronosyltransferase 1A1 expression in skin and its induction by UVB in neonatal hyperbilirubinemia.
2013 Nov
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
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
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
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
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
NSC
26685
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
MERCK INDEX
m2492
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 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
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