Bilirubin
Basic information
- CAS
18422-02-1- Standard SMILES
C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)c(CCC(=O)O)c2C)NC1=O- InChIKey
BPYKTIZUTYGOLE-IFADSCNNSA-N- Molecular formula
- C33H36N4O6
- Average molar mass
- 584.7 g/mol
- Monoisotopic mass
- 584.26348487
Overview
Bilirubin IXalpha is a member of the class of biladienes that is a linear tetrapyrrole with the dipyrrole units being of both exovinyl and endovinyl type. A product of heme degradation, it is produced in the reticuloendothelial system by the reduction of biliverdin and transported to the liver as a complex with serum albumin. It has a role as an antioxidant, a mouse metabolite and a human metabolite. It is a dicarboxylic acid and a member of biladienes. It contains a 24G7 epitope. It is a conjugate acid of a bilirubin(2-).
Names & identifiers
- Preferred name
- Bilirubin
- IUPAC
- 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
Names & synonyms
bilirubin635-65-4HematoidinHemetoidinBilirubin IX-alphaCholerythrinBilirubin IXalphaBilirubin IX alpha2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acidBilirubin test3-[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 acidRFM9X3LJ49
Show more names
DTXSID8060905NSC-2668521H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-CHEBI:169901,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic aciddelta Bilirubin3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 164 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 12
- Heavy atoms
- 43
- Formal charge
- 0
- Complexity
- 1,340
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Other Biomolecules
Solubility0.009 mg/mL at 25 °C
Physical Description
Light orange to reddish-brown solid; [Merck Index] Red powder; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
247.18 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
221.86 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 21H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-
Bilirubin: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesNot Classified
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Bilirubin has known human metabolites that include 6-[3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid and Bilirubin acyl-b-D-glucuronide (mixture).
MeSH Pharmacological ClassificationNaturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Tissue LocationsBile
Cellular LocationsCytoplasm
Metabolite PathwaysAcute Intermittent Porphyria
Uses & manufacturing
Uses
Principal bile pigment from breakdown of heme; [Merck Index]
This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
General Manufacturing Information21H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-: ACTIVE
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Related reactions
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Compound notes
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