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
Interactions of bilirubin and other ligands with ligandin.
1975 May 20
[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
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
Differential induction of heme oxygenase-1 in macrophages and hepatocytes during acetaminophen-induced hepatotoxicity in the rat: effects of hemin and biliverdin.
2002 Jun 1
[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
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
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
In vitro protein binding of teicoplanin to neonatal serum.
2004 Oct
Induction of heme oxygenase-1 in human hepatocytes to protect them from ethanol-induced cytotoxicity.
2004 Sep
[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
Goal-directed therapy of cardiac preload in induced whole-body hyperthermia.
2005 Aug
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
Evidence for induced microsomal bilirubin degradation by cytochrome P450 2A5.
2005 Nov 15
Gallbladder bile composition in patients with Crohn 's disease.
2006 Jan 7
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
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
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
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
Cytochrome P450 2A5 and bilirubin: mechanisms of gene regulation and cytoprotection.
2013 Jul 15
Mitochondrial targeting of bilirubin regulatory enzymes: An adaptive response to oxidative stress.
2015 Jan 1
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 14420-4
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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