11-Deoxytetrodotoxin

Tetrodotoxin

Last updated at: March 29, 2024

Recommended name
11-Deoxytetrodotoxin
Synonyms
(1R,5S,6R,7R,9S,11S,13S,14S)-3-amino-14-methyl-8,10-dioxa-2,4-diazatetracyclo[7.3.1.17,11.01,6]tetradec-3-ene-5,9,12,13,14-pentol, Tetrodoxin, 11-deoxy-, (4beta)-
Recommended acronym
11-deoxyTTX
Abbreviation

Progenitors

No progenitors registered

Vector Species

No vector species registered

Structure
Formula
C11H17N3O7
Exact mono-isotopic mass
303.10664989
Molfile
n/a
Alternative molfiles
n/a
SMILES
C[C@@]1([C@H]2[C@@H]3[C@@H](N=C(N[C@]34[C@@H]([C@](O2)(O[C@H]1C4O)O)O)N)O)O
Alternative SMILES
n/a
InChi key
XXUFXWUHBMGUMY-FDOMXQSUSA-N
Alternative InChi keys
n/a
InChi
1S/C11H17N3O7/c1-9(18)4-2-6(16)13-8(12)14-10(2)3(15)5(9)21-11(19,20-4)7(10)17/h2-7,15-19H,1H3,(H3,12,13,14)/t2-,3?,4-,5+,6+,7+,9+,10-,11+/m1/s1
Alternative InChis
Spectra available
Unknown
Chem files

References

Nishikawa et al, 2002
Asymmetric Total Synthesis of 11-Deoxytetrodotoxin, a Naturally Occurring Congener Publication Name: Journal of the American Chemical Society Publication Date: 2002-06-07 Toshio Nishikawa, Masanori Asai, and Minoru Isobe
Certified
False
Certified links
    n/a
Non certified reference material
False

Chemical analysis

Research
True
Standardized
False
Validated
False
Official
n/a

Structure recognition assays

Research
Unknown
Standardized
Unknown
Validated
Unknown
Official
n/a

Functional assays

Research
Unknown
Standardized
Unknown
Validated
Unknown
Official
n/a

Animal assays

Research
Unknown
Standardized
Unknown
Validated
Unknown
Official
n/a

References

Bane et al, 2016
LC-MS/MS
Regulatory status
False
Human toxic syndrome(s)
Paralytical Shellfish Poisoning
Organ system toxicity
Neurotoxicity
Risk assessment
True
Molecular targets known
True
Molecular targets
Voltage dependent sodium channel (site 1)
Toxic to aquatic animals
Unknown
TEF available
False

TEF References

Bane et al, 2014
70 μg/kg b.w. for 11-deoxy-TTX (Bane et al., 2014) compared to 10 μg/kg b.w. for TTX (Noguchi, Onuki and Arakawa, 2011), WHO working group recommends more work needed to define TEFs for all TTX analogues including oral toxicity studies
Notes
Relative toxicity in mice described experimentally but TEF not defined
Christopher Miles
Contact
Andrew Turner
Contact