Neosaxitoxin

Neosaxitoxin
Names
	IUPAC name [(3aS,4R,10aS)-5,10,10-Trihydroxy-2,6-diiminooctahydro-1H,8H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
	Other names 1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2-amino-4-(((aminocarbonyl)oxy)methyl)-3a,4,5,6,8,9-hexahydro-5-hydroxy-6-imino-, (3aS,4R,10aS)-; 1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2-amino-4-((aminocarbonyl)oxy)methyl-3a,4,5,6,8,9-hexahydro-5-hydroxy-6-imino-,(3aS,4R,10aS)-; 1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2-amino-4-((aminocarbonyl)oxy)methyl-3a,4,5,6,8,9-hexahydro-5-hydroxy-6-imino-,(3aS-(3aalpha,4alpha,10aR*))-
Identifiers
CAS Number	64296-20-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:167561;
ChemSpider	19975931;
ECHA InfoCard	100.237.662
KEGG	C17208;
PubChem CID	135562690;
UNII	6YRL8BWD9H ;
CompTox Dashboard (EPA)	DTXSID70880098 ;
	InChI InChI=1S/C10H17N7O5/c11-6-14-5-4(3-22-8(13)18)17(21)7(12)16-2-1-9(19,20)10(5,16)15-6/h4-5,12,19-21H,1-3H2,(H2,13,18)(H3,11,14,15)/t4-,5-,10-/m0/s1 Key: PPEKGEBBBBNZKS-HGRQIUPRSA-N; InChI=1/C10H17N7O5/c11-6-14-5-4(3-22-8(13)18)17(21)7(12)16-2-1-9(19,20)10(5,16)15-6/h4-5,12,19-21H,1-3H2,(H2,13,18)(H3,11,14,15)/t4-,5-,10-/m0/s1 Key: PPEKGEBBBBNZKS-HGRQIUPRBS;
	SMILES C1CN2C(=N)N([C@H]([C@H]3[C@]2(C1(O)O)NC(=N)N3)COC(=O)N)O;
Properties
Chemical formula	C10H17N7O5
Molar mass	315.286
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300
Precautionary statements	P264, P270, P301+P310, P321, P330, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Neosaxitoxin (NSTX) is included, as other saxitoxin-analogs, in a broad group of natural neurotoxic alkaloids, commonly known as the paralytic shellfish toxins (PSTs). The parent compound of PSTs, saxitoxin (STX), is a tricyclic perhydropurine alkaloid, which can be substituted at various positions, leading to more than 30 naturally occurring STX analogues. All of them are related imidazoline guanidinium derivatives.^[3]

^ United States National Library of Medicine (NLM). ChemoIDplus Advanced. Registry number: 64296-20-4 (accessed: May 12, 2012) [1]
^ National Center for Biotechnology Information (NCBI). PubChem Compound (accessed: May 12, 2012) [2]
^ Mihali TK, Kellmann R, Neilan BA (March 2009). "Characterisation of the paralytic shellfish toxin biosynthesis gene clusters in Anabaena circinalis AWQC131C and Aphanizomenon sp. NH-5". BMC Biochemistry. 10: 8. doi:10.1186/1471-2091-10-8. PMC 2679770. PMID 19331657.

[1] United States National Library of Medicine (NLM). ChemoIDplus Advanced. Registry number: 64296-20-4 (accessed: May 12, 2012) [1]

[2] National Center for Biotechnology Information (NCBI). PubChem Compound (accessed: May 12, 2012) [2]

[3] Mihali TK, Kellmann R, Neilan BA (March 2009). "Characterisation of the paralytic shellfish toxin biosynthesis gene clusters in Anabaena circinalis AWQC131C and Aphanizomenon sp. NH-5". BMC Biochemistry. 10: 8. doi:10.1186/1471-2091-10-8. PMC 2679770. PMID 19331657.

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