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 |
|
| 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 |
|---|---|---|
| Role of brain cytochrome P450 mono-oxygenases in bilirubin oxidation-specific induction and activity. | 2016-02 |
|
| Heme-regulated eIF2α kinase plays a crucial role in protecting erythroid cells against Pb-induced hemolytic stress. | 2015-03-16 |
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| Mitochondrial targeting of bilirubin regulatory enzymes: An adaptive response to oxidative stress. | 2015-01-01 |
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| Characterization of the zebrafish Ugt repertoire reveals a new class of drug-metabolizing UDP glucuronosyltransferases. | 2014-07 |
|
| Mitochondrial Channel Opener Diazoxide Attenuates Hypoxia-Induced sFlt-1 Release in Human Choriocarcinoma Cells. | 2014-04 |
|
| Developmental onset of bilirubin-induced neurotoxicity involves Toll-like receptor 2-dependent signaling in humanized UDP-glucuronosyltransferase1 mice. | 2014-02-21 |
|
| Physiological concentrations of unconjugated bilirubin prevent oxidative stress-induced hepatocanalicular dysfunction and cholestasis. | 2014-02 |
|
| Importance of UDP-glucuronosyltransferase 1A1 expression in skin and its induction by UVB in neonatal hyperbilirubinemia. | 2013-11 |
|
| Epigenetic regulation is a crucial factor in the repression of UGT1A1 expression in the human kidney. | 2013-10 |
|
| Cyclosporine A treated in vitro models induce cholestasis response through comparison of phenotype-directed gene expression analysis of in vivo Cyclosporine A-induced cholestasis. | 2013-08-29 |
|
| Cytochrome P450 2A5 and bilirubin: mechanisms of gene regulation and cytoprotection. | 2013-07-15 |
|
| 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. | 2012-11 |
|
| Metabolism of bilirubin by human cytochrome P450 2A6. | 2012-05-15 |
|
| Prevention of paraquat-induced apoptosis in human neuronal SH-SY5Y cells by lipocalin-type prostaglandin D synthase. | 2012-01 |
|
| Reduced expression of UGT1A1 in intestines of humanized UGT1 mice via inactivation of NF-κB leads to hyperbilirubinemia. | 2012-01 |
|
| Urinary excretion of bilirubin oxidative metabolites in arsenite-treated mice. | 2012 |
|
| Inducible bilirubin oxidase: a novel function for the mouse cytochrome P450 2A5. | 2011-11-15 |
|
| Displacement of bilirubin from albumin in plasma from jaundiced newborns. An in vitro study of purified Chinese herbal constituents and sulfisoxazole. | 2011-07 |
|
| In vitro inhibition of heme oxygenase isoenzymes by metalloporphyrins. | 2011-04 |
|
| 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 |
|
| Adiponectin-mediated heme oxygenase-1 induction protects against iron-induced liver injury via a PPARα dependent mechanism. | 2010-10 |
|
| Diagnostic performance of traditional hepatobiliary biomarkers of drug-induced liver injury in the rat. | 2010-08 |
|
| Global changes in gene regulation demonstrate that unconjugated bilirubin is able to upregulate and activate select components of the endoplasmic reticulum stress response pathway. | 2010-03-03 |
|
| Interaction of porphyrins with human organic anion transporting polypeptide 1B1. | 2009-11-10 |
|
| Predictive factors associated with the progression to hepatic failure caused by lamivudine-resistant HBV. | 2008-11 |
|
| 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. | 2008-10-15 |
|
| [Portal vein hypertension during azathioprine therapy in patients with Crohn's disease--a frequent phenomenon?]. | 2008-05 |
|
| Protective response of the Ah receptor to ANIT-induced biliary epithelial cell toxicity in see-through medaka. | 2008-04 |
|
| Protective effects of bilirubin against cyclophosphamide induced hemorrhagic cystitis in rats. | 2008-03 |
|
| Carbon monoxide donors or heme oxygenase-1 (HO-1) overexpression blocks interleukin-18-mediated NF-kappaB-PTEN-dependent human cardiac endothelial cell death. | 2008-02-01 |
|
| Characterization of the UDP glucuronosyltransferase activity of human liver microsomes genotyped for the UGT1A1*28 polymorphism. | 2007-12 |
|
| The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution. | 2007-09 |
|
| Heme oxygenase-1 enhances renal mitochondrial transport carriers and cytochrome C oxidase activity in experimental diabetes. | 2006-06-09 |
|
| Heme oxygenase-1 protects tumor cells against photodynamic therapy-mediated cytotoxicity. | 2006-06-08 |
|
| Glutamate induces oxidative stress and apoptosis in cerebral vascular endothelial cells: contributions of HO-1 and HO-2 to cytoprotection. | 2006-05 |
|
| Gallbladder bile composition in patients with Crohn 's disease. | 2006-01-07 |
|
| Cryopreserved fetal liver cell transplants support the chronic failing liver in rats with CCl4-induced cirrhosis. | 2006 |
|
| Evidence for induced microsomal bilirubin degradation by cytochrome P450 2A5. | 2005-11-15 |
|
| Heme oxygenase-2 protects against glutathione depletion-induced neuronal apoptosis mediated by bilirubin and cyclic GMP. | 2005-04 |
|
| [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 |
|
| Intestinal excretion of unconjugated bilirubin in man and rats with inherited unconjugated hyperbilirubinemia. | 1997-08 |
|
| Effect of growth hormone or chromium picolinate on swine metabolism and inflammatory cytokine production after endotoxin challenge exposure. | 1997-06 |
|
| [Hepatic veno-occlusive disease associated to the use of azathioprine in a renal transplant recipient]. | 1996-12 |
|
| New concepts in bilirubin and jaundice: report of the Third International Bilirubin Workshop, April 6-8, 1995, Trieste, Italy. | 1996-11 |
|
| [Apolipoprotein A in patients with alcoholic liver disease]. | 1990-03-01 |
|
| Protection of glutathione S-transferase from bilirubin inhibition. | 1989-06 |
|
| [Interrelation of bilirubin and free fatty acids in newborn infants with pathologic conditions]. | 1989-01 |
|
| Papillary necrosis in the Gunn rat: rapid induction by analgesics. | 1972-07 |
|
| Fixed drug combinations and the displacement of bilirubin from albumin. | 1971-07 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:49:22 GMT 2025
by
admin
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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| Record Version |
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89871-8
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35194-0
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54362-9
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21 CFR 862.1110
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14421-2
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1978-6
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39461-9
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14423-8
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21 CFR 862.1115
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12476-8
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1977-8
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1975-2
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14424-6
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1974-5
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42719-5
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89872-6
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72898-0
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1976-0
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35193-2
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43887-9
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21 CFR 862.1113
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59828-4
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1973-7
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14420-4
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43824-2
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C305
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D001663
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RFM9X3LJ49
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635-65-4
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5280352
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300000049353
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16990
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RFM9X3LJ49
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26685
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m2492
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PRIMARY | Merck Index | ||
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BILIRUBIN
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211-239-7
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| Related Record | Type | Details | ||
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TRANSPORTER -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE |
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TRANSPORTER -> SUBSTRATE |
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METABOLITE -> PARENT |
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