Bilirubin
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Basic Info
| Common Name | Bilirubin(F05348) |
| 2D Structure | |
| Description | Bilirubin is a bile pigment that is a degradation product of heme. In particular, bilirubin is a yellow breakdown product of normal heme catabolism. Its levels are elevated in certain diseases and it is responsible for the yellow color of bruises. Bilirubin is an excretion product, and the body does not control levels. Bilirubin levels reflect the balance between production and excretion. Thus, there is no normal level of bilirubin. Bilirubin consists of an open chain of four pyrroles (tetrapyrrole); by contrast, the heme molecule is a closed ring of four pyrroles, called porphyrin. |
| FRCD ID | F05348 |
| CAS Number | 635-65-4 |
| PubChem CID | 5280352 |
| Formula | C33H36N4O6 |
| IUPAC Name | 3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid |
| InChI Key | BPYKTIZUTYGOLE-IFADSCNNSA-N |
| InChI | 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- |
| Canonical SMILES | CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)C=C3C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)C=C4C(=C(C(=O)N4)C=C)C |
| Isomeric SMILES | CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)/C=C\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/C=C\4/C(=C(C(=O)N4)C=C)C |
| Wikipedia | Bilirubin |
| Synonyms |
Bilirubin IXalpha
bilirubin
635-65-4
Hematoidin
Hemetoidin
Principal bile pigment
UNII-RFM9X3LJ49
Bilirubin IX-alpha
EINECS 211-239-7
NSC 26685
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Tetrapyrroles and derivatives |
| Subclass | Bilirubins |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Bilirubins |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Bilirubin skeleton - Dicarboxylic acid or derivatives - Substituted pyrrole - Pyrrole - Pyrroline - Heteroaromatic compound - Secondary carboxylic acid amide - Lactam - Carboxamide group - Azacycle - Carboxylic acid - Carboxylic acid derivative - Organopnictogen compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 584.673 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 12 |
| Complexity | 1340 |
| Monoisotopic Mass | 584.263 |
| Exact Mass | 584.263 |
| XLogP | 2.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 43 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.6796 |
| Human Intestinal Absorption | HIA- | 0.5601 |
| Caco-2 Permeability | Caco2- | 0.8957 |
| P-glycoprotein Substrate | Substrate | 0.6533 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7942 |
| Non-inhibitor | 0.8972 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8870 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7887 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7919 |
| CYP450 2D6 Substrate | Non-substrate | 0.8495 |
| CYP450 3A4 Substrate | Substrate | 0.5947 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6544 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6492 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9003 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7835 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8308 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8410 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9833 |
| Non-inhibitor | 0.8939 | |
| AMES Toxicity | Non AMES toxic | 0.7856 |
| Carcinogens | Non-carcinogens | 0.9532 |
| Fish Toxicity | High FHMT | 0.8997 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9475 |
| Honey Bee Toxicity | Low HBT | 0.7060 |
| Biodegradation | Not ready biodegradable | 0.9328 |
| Acute Oral Toxicity | III | 0.5948 |
| Carcinogenicity (Three-class) | Non-required | 0.6215 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.8194 | LogS |
| Caco-2 Permeability | 0.1417 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6173 | LD50, mol/kg |
| Fish Toxicity | 1.4154 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3731 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Toxicological analysis of roast duck flavor components. | Food Chem Toxicol | 2018 Sep | 29208505 |
| Growth performance, blood parameters, carcass characteristics and meat qualitytraits in Potchefstroom Koekoek chickens fed Lippia javanica leaf meal. | Trop Anim Health Prod | 2018 May 22 | 29789988 |
| High seroprevalence of hepatitis E virus in the ethnic minority populations inYunnan, China. | PLoS One | 2018 May 22 | 29787589 |
| Effects of a combination of plant bioactive lipid compounds and biotin comparedwith monensin on body condition, energy metabolism and milk performance intransition dairy cows. | PLoS One | 2018 Mar 27 | 29584764 |
| Rechargeable, flexible and mediator-free biosupercapacitor based on transparentITO nanoparticle modified electrodes acting in µM glucose containing buffers. | Biosens Bioelectron | 2018 Mar 15 | 29049946 |
| Endogenous non-enzymatic antioxidants in the human body. | Adv Med Sci | 2018 Mar | 28822266 |
| Effects of dietary β-glucan supplementation on growth performance and immunological and metabolic parameters of weaned pigs administered with Escherichia coli lipopolysaccharide. | Food Funct | 2018 Jun 20 | 29808837 |
| Adeno-Associated Virus Serotype 2 Vector-Mediated Reintroduction of microRNA-19b Attenuates Hepatic Fibrosis. | Hum Gene Ther | 2018 Jun | 29281894 |
| Serum and whole blood Zn, Cu and Mn profiles and their relation to redox statusin lung cancer patients. | J Trace Elem Med Biol | 2018 Jan | 29173487 |
| Innocuousness of a polyherbal formulation: A case study using a traditional Thai antihypertensive herbal recipe in rodents. | Food Chem Toxicol | 2018 Feb | 28757462 |
| Assessment of liver function in pregnant anemic women upon oral iron and folicacid supplementation. | J Gynecol Obstet Hum Reprod | 2018 Feb | 29196155 |
| Protection of manganese oxide nanoparticles-induced liver and kidney damage byvitamin D. | Regul Toxicol Pharmacol | 2018 Aug 10 | 30102957 |
| Targeting the proinflammatory cytokines, oxidative stress, apoptosis andTGF-β1/STAT-3 signaling by irbesartan to ameliorate doxorubicin-inducedhepatotoxicity. | J Infect Chemother | 2018 Aug | 29753615 |
| DIVA metabolomics: Differentiating vaccination status following viral challengeusing metabolomic profiles. | PLoS One | 2018 Apr 5 | 29621258 |
| In vivo toxicological evaluation of graphene oxide nanoplatelets for clinical application. | Int J Nanomedicine | 2018 | 30174424 |
| Hepatoprotective effect of food preservatives (butylated hydroxyanisole, butylated hydroxytoluene) on carbon tetrachloride-induced hepatotoxicity in rat. | Toxicol Rep | 2018 | 29276688 |
| Bromuconazole-induced hepatotoxicity is accompanied by upregulation of PXR/CYP3A1 and downregulation of CAR/CYP2B1 gene expression. | Toxicol Mech Methods | 2017 Sep | 28532222 |
| Dietary verbascoside supplementation in donkeys: effects on milk fatty acidprofile during lactation, and serum biochemical parameters and oxidative markers. | Animal | 2017 Sep | 28264745 |
| Transparent, mediator- and membrane-free enzymatic fuel cell based onnanostructured chemically modified indium tin oxide electrodes. | Biosens Bioelectron | 2017 Nov 15 | 28554045 |
| Development and characterization of an experimental model of diet-inducedmetabolic syndrome in rabbit. | PLoS One | 2017 May 23 | 28542544 |
Targets
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
- Gene Name:
- SLCO1B1
- Uniprot ID:
- Q9Y6L6
- Molecular Weight:
- 76447.99 Da
References
- De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP: Structure-based identification of OATP1B1/3 inhibitors. Mol Pharmacol. 2013 Jun;83(6):1257-67. doi: 10.1124/mol.112.084152. Epub 2013 Apr 9. [23571415 ]
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP). Involved in the clearance of bile acids and organic anions from the liver.
- Gene Name:
- SLCO1B3
- Uniprot ID:
- Q9NPD5
- Molecular Weight:
- 77402.175 Da
References
- De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP: Structure-based identification of OATP1B1/3 inhibitors. Mol Pharmacol. 2013 Jun;83(6):1257-67. doi: 10.1124/mol.112.084152. Epub 2013 Apr 9. [23571415 ]