tetrodotoxin (CHEBI:9506)

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CHEBI:9506 - tetrodotoxin

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ChEBI Name	tetrodotoxin

ChEBI ID	CHEBI:9506

Definition	A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C11H17N3O8

Net Charge

Average Mass

319.26800

Monoisotopic Mass

319.102

InChI

InChI=1S/C11H17N3O8/c12-8-13-6(17)2-4-9(19,1-15)5-3(16)10(2,14-8)7(18)11(20,21-4)22-5/h2-7,15-20H,1H2,(H3,12,13,14)/t2-,3+,4-,5+,6-,7+,9+,10-,11+/m1/s1

InChIKey

CFMYXEVWODSLAX-QYIGHCJRSA-N

SMILES

OC[C@@]1(O)[C@H]2O[C@@]3(O)O[C@@H]1[C@@H]1[C@@H](O)NC(=N)N[C@]1([C@H]2O)[C@@H]3O

Roles Classification
Biological Role(s):	marine metabolite Any metabolite produced during a metabolic reaction in marine macro- and microorganisms. animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals. bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. voltage-gated sodium channel blocker Any sodium channel blocker that interferes with the activity of voltage-gated sodium channels. neurotoxin A poison that interferes with the functions of the nervous system. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

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ChEBI Ontology
Outgoing	tetrodotoxin (CHEBI:9506) has role animal metabolite (CHEBI:75767) tetrodotoxin (CHEBI:9506) has role bacterial metabolite (CHEBI:76969) tetrodotoxin (CHEBI:9506) has role marine metabolite (CHEBI:76507) tetrodotoxin (CHEBI:9506) has role neurotoxin (CHEBI:50910) tetrodotoxin (CHEBI:9506) has role voltage-gated sodium channel blocker (CHEBI:38634) tetrodotoxin (CHEBI:9506) is a azatetracycloalkane (CHEBI:39266) tetrodotoxin (CHEBI:9506) is a oxatetracycloalkane (CHEBI:39267) tetrodotoxin (CHEBI:9506) is a quinazoline alkaloid (CHEBI:36470)

IUPAC Name

(1R,5R,6R,7R,9S,11R,12R,13S,14S)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1^7,11.0^1,6]tetradecane-5,9,12,13,14-pentol

Synonyms	Sources
fugu poison	ChemIDplus
maculotoxin	ChemIDplus
octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-[1,3]dioxocino[6,5-d]pyrimidine-4,7,10,11,12-pentol	ChEBI
spheroidine	ChemIDplus
tarichatoxin	ChemIDplus
tetrodontoxin	ChemIDplus
Tetrodotoxin	KEGG COMPOUND
TTX	KEGG COMPOUND
TTX	ChemIDplus

Database Links	Databases
C11692	KEGG COMPOUND
DB05232	DrugBank
Tetrodotoxin	Wikipedia
View more database links

Registry Numbers	Types	Sources
4156319	Beilstein Registry Number	Beilstein
4368-28-9	CAS Registry Number	KEGG COMPOUND
4368-28-9	CAS Registry Number	ChemIDplus
6072946	Reaxys Registry Number	Reaxys

Citations	Types	Sources
22163187	PubMed citation	Europe PMC
22412801	PubMed citation	Europe PMC
22798951	PubMed citation	Europe PMC
23261990	PubMed citation	Europe PMC
23661608	PubMed citation	Europe PMC
23866757	PubMed citation	Europe PMC
23980434	PubMed citation	Europe PMC
24121556	PubMed citation	Europe PMC
24295175	PubMed citation	Europe PMC
24566728	PubMed citation	Europe PMC

Last Modified

04 August 2014