Bilirubin

Bilirubin
Names
	IUPAC name 3,3′-(2,17-Diethenyl-3,7,13,18-tetramethyl-1,19-dioxo-10,19,21,22,23,24-hexahydro-1H-biline-8,12-diyl)dipropanoic acid
	Systematic IUPAC name 3,3′-([12(2)Z,6(72)Z]-13,74-Diethenyl-14,33,54,73-tetramethyl-15,75-dioxo-11,15,71,75-tetrahydro-31H,51H-1,7(2),3,5(2,5)-tetrapyrrolaheptaphane-12(2),6(72)-diene-34,53-diyl)dipropanoic acid
	Other names Bilirubin IXα
Identifiers
CAS Number	635-65-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:16990 ;
ChEMBL	ChEMBL501680 ;
ChemSpider	4444055 ;
ECHA InfoCard	100.010.218
IUPHAR/BPS	4577;
PubChem CID	5280352;
UNII	RFM9X3LJ49 ;
CompTox Dashboard (EPA)	DTXSID8060905 DTXSID90239827, DTXSID8060905 ;
	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- Key: BPYKTIZUTYGOLE-IFADSCNNSA-N ; Key: BPYKTIZUTYGOLE-IFADSCNNBS;
	SMILES CC1=C(/C=C2C(C)=C(C=C)C(N/2)=O)NC(CC3=C(CCC(O)=O)C(C)=C(/C=C4C(C=C)=C(C)C(N/4)=O)N3)=C1CCC(O)=O; Cc1c(c([nH]c1/C=C\2/C(=C(C(=O)N2)C=C)C)Cc3c(c(c([nH]3)/C=C\4/C(=C(C(=O)N4)C)C=C)C)CCC(=O)O)CCC(=O)O;
Properties
Chemical formula	C33H36N4O6
Molar mass	584.673 g·mol−1
Density	1.31 g·cm-3
Melting point	235°C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Bilirubin (BR) (adopted from German, originally bili, for bile, plus ruber, Latin for red) is a red-orange compound that occurs as the reduction product of biliverdin, a breakdown product of heme. It's further broken down in the colon to urobilinogen, most of which becomes stercobilin, causing the brown color of feces. Some unconverted urobilinogen, metabolised to urobilin, provides the straw-yellow color in urine.^[3]

Although bilirubin is usually found in animals rather than plants, at least one plant species, Strelitzia nicolai, is known to contain the pigment.^[4]

^ Bonnett, Raymond; Davies, John E.; Hursthouse, Michael B. (July 1976). "Structure of bilirubin". Nature. 262 (5566): 326–328. Bibcode:1976Natur.262..326B. doi:10.1038/262326a0. PMID 958385. S2CID 4278361.
^ Sturrock, E. D.; Bull, J. R.; Kirsch, R. E. (March 1994). "The synthesis of [10-13C]bilirubin IXα". Journal of Labelled Compounds and Radiopharmaceuticals. 34 (3): 263–274. doi:10.1002/jlcr.2580340309.
^ Chew, Dennis J.; DiBartola, Stephen P.; Schenck, Patricia A. (1 January 2011), Chew, Dennis J.; DiBartola, Stephen P.; Schenck, Patricia A. (eds.), "Chapter 1 - Urinalysis", Canine and Feline Nephrology and Urology (Second Edition), Saint Louis: W.B. Saunders, pp. 1–31, ISBN 978-0-7216-8178-8, retrieved 1 November 2023
^ Pirone C, Quirke JM, Priestap HA, Lee DW (March 2009). "Animal pigment bilirubin discovered in plants". Journal of the American Chemical Society. 131 (8): 2830. doi:10.1021/ja809065g. PMC 2880647. PMID 19206232.

[Reaxys-1] Bonnett, Raymond; Davies, John E.; Hursthouse, Michael B. (July 1976). "Structure of bilirubin". Nature. 262 (5566): 326–328. Bibcode:1976Natur.262..326B. doi:10.1038/262326a0. PMID 958385. S2CID 4278361.

[Reaxysb-2] Sturrock, E. D.; Bull, J. R.; Kirsch, R. E. (March 1994). "The synthesis of [10-13C]bilirubin IXα". Journal of Labelled Compounds and Radiopharmaceuticals. 34 (3): 263–274. doi:10.1002/jlcr.2580340309.

[3] Chew, Dennis J.; DiBartola, Stephen P.; Schenck, Patricia A. (1 January 2011), Chew, Dennis J.; DiBartola, Stephen P.; Schenck, Patricia A. (eds.), "Chapter 1 - Urinalysis", Canine and Feline Nephrology and Urology (Second Edition), Saint Louis: W.B. Saunders, pp. 1–31, ISBN 978-0-7216-8178-8, retrieved 1 November 2023

[pmid19206232-4] Pirone C, Quirke JM, Priestap HA, Lee DW (March 2009). "Animal pigment bilirubin discovered in plants". Journal of the American Chemical Society. 131 (8): 2830. doi:10.1021/ja809065g. PMC 2880647. PMID 19206232.

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