Mycolactone

Mycolactone
Names
	Preferred IUPAC name (6S,7S,9E,12R)-12-[(2S,4E,6R,7R,9R)-7,9-Dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2E,4E,6E,8E,10E,12S,13S,15S)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate
Identifiers
CAS Number	222050-77-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	4445303 ;
MeSH	Mycolactone
PubChem CID	5282079;
CompTox Dashboard (EPA)	DTXSID10415207 ;
	InChI InChI=1S/C44H70O9/c1-28(13-11-14-29(2)25-39(48)40(49)27-37(10)46)21-30(3)18-20-44(51)52-41-15-12-16-43(50)53-42(19-17-31(4)22-34(41)7)35(8)24-32(5)23-33(6)38(47)26-36(9)45/h11,13-14,17-18,20-21,23,25,33-42,45-49H,12,15-16,19,22,24,26-27H2,1-10H3/b14-11+,20-18+,28-13+,29-25+,30-21+,31-17+,32-23+/t33-,34+,35+,36-,37+,38-,39+,40+,41+,42-/m1/s1 Key: WKTLNJXZVDLRTJ-QRRXZRELSA-N ; InChI=1/C44H70O9/c1-28(13-11-14-29(2)25-39(48)40(49)27-37(10)46)21-30(3)18-20-44(51)52-41-15-12-16-43(50)53-42(19-17-31(4)22-34(41)7)35(8)24-32(5)23-33(6)38(47)26-36(9)45/h11,13-14,17-18,20-21,23,25,33-42,45-49H,12,15-16,19,22,24,26-27H2,1-10H3/b14-11+,20-18+,28-13+,29-25+,30-21+,31-17+,32-23+/t33-,34+,35+,36-,37+,38-,39+,40+,41+,42-/m1/s1 Key: WKTLNJXZVDLRTJ-QRRXZRELBE;
	SMILES O=C1O[C@H](C/C=C(/C[C@@H]([C@@H](OC(=O)\C=C\C(=C\C(=C\C=C\C(=C\[C@H](O)[C@@H](O)C[C@@H](O)C)C)C)C)CCC1)C)C)[C@@H](C)CC(=C/[C@@H](C)[C@H](O)C[C@H](O)C)/C;
Properties
Chemical formula	C44H70O9
Molar mass	743.021
	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

Mycolactone is a polyketide-derived macrolide produced and secreted by a group of very closely related pathogenic mycobacteria species including M. ulcerans, M. liflandii (an unofficial designation), M. pseudoshottsii, and some strains of M. marinum. These mycobacteria are collectively referred to as mycolactone-producing mycobacteria or MPM.^[1]^[2]

In humans, mycolactone is the toxin responsible for Buruli ulcers, doing so by damaging tissues and inhibiting the immune response.^[3]

^ Yip MJ, Porter JL, Fyfe JA, Lavender CJ, et al. (March 2007). "Evolution of Mycobacterium ulcerans and other mycolactone-producing mycobacteria from a common Mycobacterium marinum progenitor". J. Bacteriol. 189 (5): 2021–29. doi:10.1128/JB.01442-06. PMC 1855710. PMID 17172337.
^ Käser M; Hauser J; Small P; Pluschke G. (September 2009). "Large sequence polymorphisms unveil the phylogenetic relationship of environmental and pathogenic mycobacteria related to "Mycobacterium ulcerans"". Appl Environ Microbiol. 75 (17): 5667–75. Bibcode:2009ApEnM..75.5667K. doi:10.1128/AEM.00446-09. PMC 2737907. PMID 19592526.
^ "Buruli ulcer disease". Fact sheets. WHO. March 2007. Retrieved 24 March 2012.

[Yip-1] Yip MJ, Porter JL, Fyfe JA, Lavender CJ, et al. (March 2007). "Evolution of Mycobacterium ulcerans and other mycolactone-producing mycobacteria from a common Mycobacterium marinum progenitor". J. Bacteriol. 189 (5): 2021–29. doi:10.1128/JB.01442-06. PMC 1855710. PMID 17172337.

[Käser-2] Käser M; Hauser J; Small P; Pluschke G. (September 2009). "Large sequence polymorphisms unveil the phylogenetic relationship of environmental and pathogenic mycobacteria related to "Mycobacterium ulcerans"". Appl Environ Microbiol. 75 (17): 5667–75. Bibcode:2009ApEnM..75.5667K. doi:10.1128/AEM.00446-09. PMC 2737907. PMID 19592526.

[3] "Buruli ulcer disease". Fact sheets. WHO. March 2007. Retrieved 24 March 2012.

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