tetrodotoxin   

GtoPdb Ligand ID: 2616

Synonyms: TTX
Comment: Tetrodotoxin is a potent neurotoxin found in certain fish and other aquatic animals, although it is actually produced in symbiotic bacteria hosted in these creatures.
There is some ambiguity in the literature and on other databases as to the exact stereochemistry of tetrodotoxin. Our structure matches that on ChEBI and the PubChem entry linked to above, while the compound is also represented by the alternative isomer in CHEMBL507974 and CID 11174599.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: tetrodotoxin

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 11
Hydrogen bond donors 8
Rotatable bonds 1
Topological polar surface area 190.25
Molecular weight 319.1
XLogP -3.58
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES OCC1(O)C2OC3(OC1C1C(C2O)(C3O)NC(=NC1O)N)O
Isomeric SMILES OC[C@@]1(O)[C@H]2O[C@]3(O[C@@H]1[C@H]1[C@@]([C@H]2O)([C@@H]3O)NC(=N[C@@H]1O)N)O
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
InChI Key CFMYXEVWODSLAX-QYIGHCJRSA-N
References
1. Akopian AN, Sivilotti L, Wood JN. (1996)
A tetrodotoxin-resistant voltage-gated sodium channel expressed by sensory neurons.
Nature, 379 (6562): 257-62. [PMID:8538791]
2. Bricelj VM, Connell L, Konoki K, Macquarrie SP, Scheuer T, Catterall WA, Trainer VL. (2005)
Sodium channel mutation leading to saxitoxin resistance in clams increases risk of PSP.
Nature, 434 (7034): 763-7. [PMID:15815630]
3. Chahine M, Bennett PB, George Jr AL, Horn R. (1994)
Functional expression and properties of the human skeletal muscle sodium channel.
Pflugers Arch., 427 (1-2): 136-42. [PMID:8058462]
4. Chen YH, Dale TJ, Romanos MA, Whitaker WR, Xie XM, Clare JJ. (2000)
Cloning, distribution and functional analysis of the type III sodium channel from human brain.
Eur. J. Neurosci., 12 (12): 4281-9. [PMID:11122339]
5. Cribbs LL, Satin J, Fozzard HA, Rogart RB. (1990)
Functional expression of the rat heart I Na+ channel isoform. Demonstration of properties characteristic of native cardiac Na+ channels.
FEBS Lett., 275 (1-2): 195-200. [PMID:2175715]
6. Cummins TR, Dib-Hajj SD, Black JA, Akopian AN, Wood JN, Waxman SG. (1999)
A novel persistent tetrodotoxin-resistant sodium current in SNS-null and wild-type small primary sensory neurons.
J. Neurosci., 19 (24): RC43. [PMID:10594087]
7. Dietrich PS, McGivern JG, Delgado SG, Koch BD, Eglen RM, Hunter JC, Sangameswaran L. (1998)
Functional analysis of a voltage-gated sodium channel and its splice variant from rat dorsal root ganglia.
J. Neurochem., 70 (6): 2262-72. [PMID:9603190]
8. Klugbauer N, Lacinova L, Flockerzi V, Hofmann F. (1995)
Structure and functional expression of a new member of the tetrodotoxin-sensitive voltage-activated sodium channel family from human neuroendocrine cells.
EMBO J., 14 (6): 1084-90. [PMID:7720699]
9. Sangameswaran L, Fish LM, Koch BD, Rabert DK, Delgado SG, Ilnicka M, Jakeman LB, Novakovic S, Wong K, Sze P et al.. (1997)
A novel tetrodotoxin-sensitive, voltage-gated sodium channel expressed in rat and human dorsal root ganglia.
J. Biol. Chem., 272 (23): 14805-9. [PMID:9169448]
10. Smith MR, Smith RD, Plummer NW, Meisler MH, Goldin AL. (1998)
Functional analysis of the mouse Scn8a sodium channel.
J. Neurosci., 18 (16): 6093-102. [PMID:9698304]
11. Smith RD, Goldin AL. (1998)
Functional analysis of the rat I sodium channel in xenopus oocytes.
J. Neurosci., 18 (3): 811-20. [PMID:9437003]
12. Trimmer JS, Cooperman SS, Tomiko SA, Zhou JY, Crean SM, Boyle MB, Kallen RG, Sheng ZH, Barchi RL, Sigworth FJ et al.. (1989)
Primary structure and functional expression of a mammalian skeletal muscle sodium channel.
Neuron, 3 (1): 33-49. [PMID:2559760]
13. Zeng D, Kyle JW, Martin RL, Ambler KS, Hanck DA. (1996)
Cardiac sodium channels expressed in a peripheral neurotumor-derived cell line, RT4-B8.
Am. J. Physiol., 270 (5 Pt 1): C1522-31. [PMID:8967455]