Cylindrospermopsin

Cylindrospermopsin
Names
	IUPAC name 2,4(1H,3H)-Pyrimidinedione, 6-[(R)-hydroxy[(2aS,3R,4S,5aS,7R) -2,2a,3,4,5,5a,6,7-octahydro-3-methyl-4-(sulfooxy) -1H-1,8,8b-triazaacenaphthylen-7-yl]methyl]-
	Other names Cylindrospermopsine
Identifiers
CAS Number	143545-90-8 ; 265652-18-4 7-epi;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:26502525 ; CHEBI:88049 7-epi;
ChEMBL	ChEMBL1722002;
ChemSpider	21106433 ;
ECHA InfoCard	100.229.780
KEGG	C19999;
PubChem CID	42628600; 115005 7-epi;
UNII	2JIZ556BA3;
CompTox Dashboard (EPA)	DTXSID2031083 ;
	InChI InChI=1S/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/p+1/t6-,7+,8-,10?,11+,13+/m1/s1 Key: LHJPHMKIGRLKDR-NPSYHWQSSA-O ; InChI=1/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/p+1/t6-,7+,8-,10?,11+,13+/m1/s1 Key: LHJPHMKIGRLKDR-FGVRTCLEBA;
	SMILES O=C1/C=C(\N=C(\O)N1)[C@@H](O)[C@H]2C[C@H]4C[C@H](OS(O)(=O)=O)[C@H](C)C3C\[NH+]=C(\N2)N34;
Properties
Chemical formula	C15H21N5O7S
Molar mass	415.43
Appearance	White solid
Solubility in water	High
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H341, H370
Precautionary statements	P201, P202, P260, P264, P270, P281, P301+P310, P307+P311, P308+P313, P321, P330, P405, P501
	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

Cylindrospermopsin (abbreviated to CYN, or CYL) is a cyanotoxin produced by a variety of freshwater cyanobacteria. CYN is a polycyclic uracil derivative containing guanidino and sulfate groups. It is also zwitterionic, making it highly water soluble. CYN is toxic to liver and kidney tissue and is thought to inhibit protein synthesis and to covalently modify DNA and/or RNA. It is not known whether cylindrospermopsin is a carcinogen, but it appears to have no tumour-initiating activity in mice.

CYN was first discovered after an outbreak of a mystery disease on Palm Island, Queensland, Australia. The outbreak was traced to a bloom of Cylindrospermopsis raciborskii in the local drinking water supply, and the toxin was subsequently identified. Analysis of the toxin led to a proposed chemical structure in 1992, which was revised after synthesis was achieved in 2000. Several analogues of CYN, both toxic and non-toxic, have been isolated or synthesised.

C. raciborskii has been observed mainly in tropical areas, but has also been observed in temperate regions of Australia, North, South America, New Zealand and Europe. The CYN-producing strain of C. raciborskii has not been identified in Europe, but several other European cyanobacteria species are CYN-producing.