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CHEBI:9506 - tetrodotoxin

Default Structure
ChEBI IDCHEBI:9506
ChEBI Nametetrodotoxin
Stars
DefinitionA 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.
Last Modified13 September 2021
DownloadsMolfile
FormulaC11H17N3O8
Net Charge0
Average Mass319.270
Monoisotopic Mass319.10156
SMILES[H][C@]1(O)[C@]2([H])O[C@@]3(O)O[C@@]([H])([C@@]2(O)CO)[C@@]2([H])[C@]1(NC(=N)N[C@]2([H])O)[C@]3([H])O
InChIInChI=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
InChIKeyCFMYXEVWODSLAX-QYIGHCJRSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Crassostrea gigas (ncbitaxon:29159) - PubMed (33540777)
Lagocephalus sceleratus (ncbitaxon:229057) - PubMed (31833474)
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
neurotoxin  A poison that interferes with the functions of the nervous system.
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
voltage-gated sodium channel blocker  Any sodium channel blocker that interferes with the activity of voltage-gated sodium channels.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
(+/-)-tetrodotoxin (CHEBI:209255) has functional parent tetrodotoxin (CHEBI:9506)
(11s,13s)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1~7,11~.0~1,6~]tetradec-3-ene-5,9,12,13,14-pentol (CHEBI:229828) has functional parent tetrodotoxin (CHEBI:9506)
(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)
Anhydrotetrodotoxin (CHEBI:221694) 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  Source
BJT 1ChemIDplus
Babylonia japonica toxin 1ChemIDplus
fugu poisonChemIDplus
maculotoxinChemIDplus
octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-[1,3]dioxocino[6,5-d]pyrimidine-4,7,10,11,12-pentolChEBI
spheroidineChemIDplus
Manual XrefsDatabases
C00055525KNApSAcK
C11692KEGG COMPOUND
CPD-19561MetaCyc
DB05232DrugBank
HMDB0258938HMDB
TetrodotoxinWikipedia
Registry NumbersSources
Beilstein:4156319Beilstein
Reaxys:6072946Reaxys
CAS:4368-28-9KEGG COMPOUND
CAS:4368-28-9ChemIDplus
Citations