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.

Supplier Information	ZINC000096085405

Download	Molfile XML SDF

more structures >>

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Mrv0541 03241413343D

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Mrv0541 03241413343D

39 42 0 0 1 0 999 V2000

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0.5444 -1.0801 -0.3286 C 0 0 1 0 0 0 0 0 0 0 0 0

2.2014 0.5495 0.6206 C 0 0 1 0 0 0 0 0 0 0 0 0

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-0.1368 0.7769 1.2756 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.7512 1.0246 2.1445 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4000 -0.7155 0.8823 C 0 0 2 0 0 0 0 0 0 0 0 0

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0.3470 -0.0706 -1.5208 C 0 0 2 0 0 0 0 0 0 0 0 0

1.2019 -0.3815 -2.6241 O 0 0 0 0 0 0 0 0 0 0 0 0

0.6189 1.3794 -1.0137 C 0 0 2 0 0 0 0 0 0 0 0 0

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2.7388 -1.1630 -0.6255 H 0 0 0 0 0 0 0 0 0 0 0 0

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0.9082 -2.8506 -1.2418 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5505 1.7469 1.3019 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2660 -2.7195 0.9000 H 0 0 0 0 0 0 0 0 0 0 0 0

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0.8002 3.4691 0.9595 H 0 0 0 0 0 0 0 0 0 0 0 0

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17 37 1 0 0 0 0

22 38 1 0 0 0 0

23 39 1 0 0 0 0

M END): 30 ms

reading 39 atoms

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39 atoms created

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Wikipedia	License
[object Object]
Read full article at Wikipedia

Formula

C11H17N3O8

Net Charge

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 )

View more via ChEBI Ontology

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	(+/-)-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[7.3.1.1^7,11.0^1,6]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

Citations	Types	Sources
11024497	PubMed citation	Europe PMC
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
28648727	PubMed citation	Europe PMC
28817087	PubMed citation	Europe PMC
31029635	PubMed citation	Europe PMC
31833474	PubMed citation	Europe PMC
31985136	PubMed citation	Europe PMC
32210160	PubMed citation	Europe PMC
32415408	PubMed citation	Europe PMC
32625458	PubMed citation	Europe PMC
32849450	PubMed citation	Europe PMC
33276679	PubMed citation	Europe PMC
33450969	PubMed citation	Europe PMC
33540777	PubMed citation	Europe PMC
33651884	PubMed citation	Europe PMC
33805908	PubMed citation	Europe PMC
33807311	PubMed citation	Europe PMC
33830775	PubMed citation	Europe PMC
33913398	PubMed citation	Europe PMC
33955768	PubMed citation	Europe PMC
34067828	PubMed citation	Europe PMC
34207879	PubMed citation	Europe PMC
34209313	PubMed citation	Europe PMC
34273772	PubMed citation	Europe PMC
34357955	PubMed citation	Europe PMC
34357968	PubMed citation	Europe PMC
34437388	PubMed citation	Europe PMC
34454925	PubMed citation	Europe PMC
9559733	PubMed citation	Europe PMC
IND607175662	Agricola citation	Europe PMC

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.

CHEBI:9506 - tetrodotoxin

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