U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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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
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
Hepatitis C virus infection as a likely etiology of intrahepatic cholangiocarcinoma.
2004 Jul
Importance of serum bile acids determination in adolescents with juvenile hyperbilirubinaemia.
2004 Jun
In vitro protein binding of teicoplanin to neonatal serum.
2004 Oct
[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
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
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
Evidence for induced microsomal bilirubin degradation by cytochrome P450 2A5.
2005 Nov 15
Impaired expression of hepatic multidrug resistance protein 2 is associated with posthepatectomy hyperbilirubinemia in patients with biliary cancer.
2005 Sep
[Portal vein hypertension during azathioprine therapy in patients with Crohn's disease--a frequent phenomenon?].
2008 May
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
Characterization of the zebrafish Ugt repertoire reveals a new class of drug-metabolizing UDP glucuronosyltransferases.
2014 Jul
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:49:22 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:22 GMT 2025
Record UNII
RFM9X3LJ49
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-26685
Preferred Name English
BILIRUBIN
MI  
Common Name 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 Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
MESH
D001663
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
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
SMS_ID
300000049353
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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
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
BILIRUBIN
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
ECHA (EC/EINECS)
211-239-7
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
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