Prodigiosin

Prodigiosin
Names
	IUPAC name 4-Methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1′H-2,2′-bipyrrole
Identifiers
CAS Number	82-89-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82758 ;
ChEMBL	ChEMBL275787 ;
ChemSpider	10577755 ;
MeSH	Prodigiosin
PubChem CID	5351169;
UNII	OL369FU7CJ ;
	InChI InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12+ Key: SZXDNGVQRDTJSD-FOWTUZBSSA-N ; InChI=1/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12+ Key: SZXDNGVQRDTJSD-FOWTUZBSBS;
	SMILES CCCCCc3cc(=Cc2[nH]c(c1ccc[nH]1)cc2OC)nc3C;
Properties
Chemical formula	C20H25N3O
Molar mass	323.440 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Prodigiosin is the red dye produced by many strains of the bacterium Serratia marcescens,^[1]^[2] as well as other Gram-negative, gamma proteobacteria such as Vibrio psychroerythrus and Hahella chejuensis. It is responsible for the pink tint occasionally found in grime that accumulates on porcelain surfaces such as bathtubs, sinks, and toilet bowls. It is in the prodiginine family of compounds which are produced in some Gram-negative gamma proteobacteria, as well as select Gram-positive Actinobacteria (e.g. Streptomyces coelicolor).^[3] The name prodigiosin is derived from prodigious (i.e. something marvelous).

^ Bennett JW, Bentley R (2000). "Seeing red: The story of prodigiosin". Adv Appl Microbiol. Advances in Applied Microbiology. 47: 1–32. doi:10.1016/S0065-2164(00)47000-0. ISBN 9780120026470. PMID 12876793.
^ Yu, Victor L. (1979). "Serratia marcescens — Historical Perspective and Clinical Review". New England Journal of Medicine. 300 (16): 887–893. doi:10.1056/NEJM197904193001604. PMID 370597.
^ Williamson NR, Fineran PC, Gristwood T, Leeper FJ, Salmond GP (2006). "The biosynthesis and regulation of bacterial prodiginines". Nature Reviews Microbiology. 4 (12): 887–899. doi:10.1038/nrmicro1531. PMID 17109029. S2CID 11649828.

[1] Bennett JW, Bentley R (2000). "Seeing red: The story of prodigiosin". Adv Appl Microbiol. Advances in Applied Microbiology. 47: 1–32. doi:10.1016/S0065-2164(00)47000-0. ISBN 9780120026470. PMID 12876793.

[Yu-2] Yu, Victor L. (1979). "Serratia marcescens — Historical Perspective and Clinical Review". New England Journal of Medicine. 300 (16): 887–893. doi:10.1056/NEJM197904193001604. PMID 370597.

[Williamson-3] Williamson NR, Fineran PC, Gristwood T, Leeper FJ, Salmond GP (2006). "The biosynthesis and regulation of bacterial prodiginines". Nature Reviews Microbiology. 4 (12): 887–899. doi:10.1038/nrmicro1531. PMID 17109029. S2CID 11649828.

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