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
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-
Molecular Formula | C33H36N4O6 |
Molecular Weight | 584.6621 |
Charge | 0 |
Count |
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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
Title | Date | PubMed |
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Fixed drug combinations and the displacement of bilirubin from albumin. | 1971 Jul |
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Papillary necrosis in the Gunn rat: rapid induction by analgesics. | 1972 Jul |
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Protection of glutathione S-transferase from bilirubin inhibition. | 1989 Jun |
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[Hepatic veno-occlusive disease associated to the use of azathioprine in a renal transplant recipient]. | 1996 Dec |
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Hepatitis C virus infection as a likely etiology of intrahepatic cholangiocarcinoma. | 2004 Jul |
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Importance of serum bile acids determination in adolescents with juvenile hyperbilirubinaemia. | 2004 Jun |
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In vitro protein binding of teicoplanin to neonatal serum. | 2004 Oct |
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[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 |
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Heme oxygenase-2 protects against glutathione depletion-induced neuronal apoptosis mediated by bilirubin and cyclic GMP. | 2005 Apr |
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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 |
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Goal-directed therapy of cardiac preload in induced whole-body hyperthermia. | 2005 Aug |
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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 |
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Evidence for induced microsomal bilirubin degradation by cytochrome P450 2A5. | 2005 Nov 15 |
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Impaired expression of hepatic multidrug resistance protein 2 is associated with posthepatectomy hyperbilirubinemia in patients with biliary cancer. | 2005 Sep |
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[Portal vein hypertension during azathioprine therapy in patients with Crohn's disease--a frequent phenomenon?]. | 2008 May |
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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 |
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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
Edited
Mon Mar 31 17:49:22 GMT 2025
by
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on
Mon Mar 31 17:49:22 GMT 2025
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Record UNII |
RFM9X3LJ49
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Record Status |
Validated (UNII)
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m2492
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BILIRUBIN
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TRANSPORTER -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE |
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TRANSPORTER -> SUBSTRATE |
MINOR
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TRANSPORTER -> SUBSTRATE |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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