Bilirubin

• Catalog Number: ACM635654
• Product Name: Bilirubin
• CAS: 635-65-4
• Category: Heterocyclic Organic Compound
• Description: Bilirubin (formerly referred to as haematoidin) is a yellow compound that occurs in the normal catabolic pathway that breaks down heme in vertebrates. This catabolism is a necessary process in the body’s clearance of waste products that arise from the destruction of aged red blood cells. First the hemoglobin gets stripped of the heme molecule which thereafter passes through various processes of porphyrin catabolism, depending on the part of the body in which the breakdown occurs. For example, the molecules excreted in the urine differ from those in the feces. The production of biliverdin from heme is the first major step in the catabolic pathway, after which the enzyme biliverdin reductase performs the second step, producing bilirubin from biliverdin.Bilirubin is excreted in bile and urine, and elevated levels may indicate certain diseases. It is responsible for the yellow color of bruises and the yellow discoloration in jaundice. Its subsequent breakdown products, such as stercobilin, cause the brown color of feces. A different breakdown product, urobilin, is the main component of the straw-yellow color in urine.It has also been found in plants.
• Synonyms: Cholerythrin
• 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
• Molecular Weight: 584.66
• Molecular Formula: C33H36N4O6
• 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
• 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-
• InChI Key: BPYKTIZUTYGOLE-IFADSCNNSA-N
• Boiling Point: 641.7 °C
• Melting Point: 192 °C
• Flash Point: 513.3 °C
• Density: 1.2163 g/cm³
• Solubility: Practically insoluble in water
• Appearance: Solid
• Storage: -20 °C
• Complexity: 1340
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Exact Mass: 584.26348488
• Hazard Codes: Xn
• Hazard Statements: Xn
• Heavy Atom Count: 43
• HS Code: 29339990
• Hydrogen Bond Acceptor Count: 6
• Hydrogen Bond Donor Count: 6
• 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
• LogP: 5.18880
• Monoisotopic Mass: 584.26348488
• Physical State: Powder
• pKa: 4.62±0.10(Predicted)
• PSA: 164.38
• Refractive Index: 1.6000
• Rotatable Bond Count: 12
• Safety Description: 22-24/25-36-26
• Stability: Stable. Refrigerate.
• Storage Conditions: -20ºC
• Topological Polar Surface Area: 164 Ų
• WGK Germany: 2

Custom Q&A

What is the PubChem CID for bilirubin?

PubChem CID 5280352.

What is the molecular formula of bilirubin?

The molecular formula of bilirubin is C33H36N4O6.

What is the molecular weight of bilirubin?

The molecular weight of bilirubin is 584.7 g/mol.

What are some synonyms for bilirubin?

Some synonyms for bilirubin include hematoidin, hemetoidin, and bilirubin IX-alpha.

What is the IUPAC name of bilirubin?

The IUPAC name of bilirubin is 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.

What is the InChI of bilirubin?

The InChI of bilirubin is 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-.

What is the molecular structure of bilirubin?

The molecular structure of bilirubin is a linear tetrapyrrole with dipyrrole units of both exovinyl and endovinyl type.

How is bilirubin produced in the body?

Bilirubin is produced in the reticuloendothelial system by the reduction of biliverdin and is transported to the liver as a complex with serum albumin.

What is the role of bilirubin in the body?

Bilirubin has a role as an antioxidant, a human metabolite, and a mouse metabolite.

Where is bilirubin naturally found?

Bilirubin is naturally found in Houttuynia cordata, Punica granatum, and other organisms.