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 0
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[7.3.1.17,11.01,6]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
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Registry Numbers Types Sources
4156319 Beilstein Registry Number Beilstein
4368-28-9 CAS Registry Number ChemIDplus
6072946 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
22163187 PubMed citation Europe PMC
22412801 PubMed citation Europe PMC
22798951 PubMed citation Europe PMC
23261990 PubMed citation Europe PMC
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23866757 PubMed citation Europe PMC
23980434 PubMed citation Europe PMC
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Last Modified
23 August 2017