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 319.10156
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
Metabolite of Species Details
Lagocephalus sceleratus (NCBI:txid229057) See: PubMed
Crassostrea gigas (NCBI:txid29159) See: PubMed
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)
tetrodotoxin (CHEBI:9506) is conjugate base of tetrodotoxin(1+) (CHEBI:180459)
Incoming (11S,13S)-3-Amino-5,12,13,14-tetrahydroxy-14-(hydroxymethyl)-8,10-dioxa-2-aza-4-azoniatetracyclo[7.3.1.17,11.01,6]tetradec-3-en-9-olate (CHEBI:182163) has functional parent tetrodotoxin (CHEBI:9506)
tetrodotoxin(1+) (CHEBI:180459) is conjugate acid of tetrodotoxin (CHEBI:9506)
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
Babylonia japonica toxin 1 ChemIDplus
BJT 1 ChemIDplus
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
tetrodotoxine ChemIDplus
TTX KEGG COMPOUND
Manual Xrefs Databases
C00055525 KNApSAcK
C11692 KEGG COMPOUND
CPD-19561 MetaCyc
DB05232 DrugBank
HMDB0258938 HMDB
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
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Last Modified
13 September 2021
General Comment
2021-09-13 It is generally thought that tetrodotoxin in pufferfish accumulates via the food webs, beginning with marine bacteria as a primary producer.