Compound: TETRODOTOXIN
SMILES: O1[C@]2(O[C@@H]3[C@@H]4[C@@H](O)N=C(N[C@@]4([C@@H]2O)[C@@H]([C@H]1[C@]3(O)CO)O)N)O
InChIKey: CFMYXEVWODSLAX-QOZOJKKESA-N
Synonyms: TETRODOTOXIN, Tarichatoxin, Spheroidine, Tetrodotoxine, Tetrodoxin, Babylonia japonica toxin 1, Maculotoxin, 4368-28-9, Tectin, BJT 1, Pft-1 toxin, Tetrodontoxin, tetrodotoxina, Fugu poison, 3KUM2721U9, (4R-(4alpha,4aalpha,5alpha,7alpha,9alpha,10alpha,10abeta,11S*,12S*))-Octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-(1,3)dioxocino(6,5-d) pyrimidine-4,7,10,11,12-pentol, Octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol, DTXSID10881342, Tetradotoxin, Toxin, Fugu, 5,9:7,10A-DIMETHANO-10AH-(1,3)DIOXOCINO(6,5-D)PYRIMIDINE-4,7,10,11,12-PENTOL, 2-AMINO-1,4,4A,5,9,10-HEXAHYDRO-12-(HYDROXYMETHYL)-, (4R,4AR,5R,7S,9S,10S,10AR,11S,12S)-, 5,9:7,10a-Dimethano-10aH-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol, octahydro-12-(hydroxymethyl)-2-imino-, CHEBI:9506, tetrodotoxinum, (1R,5R,6R,7R,9S,11S,12S,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo(7.3.1.17,11.01,6)tetradec-3-ene-5,9,12,13,14-pentol, (1R,5R,6R,7R,9S,11S,12S,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.17,11.01,6]tetradec-3-ene-5,9,12,13,14-pentol, RefChem:6297, DTXCID101022591, (11S,13S)-3-amino-5,12,13,14-tetrahydroxy-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo(7.3.1.17,11.01,6)tetradec-3-en-4-ium-9-olate, (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, (1R,5R,6R,7R,9S,11S,12R,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo(7.3.1.17,11.01,6)tetradec-3-ene-5,9,12,13,14-pentol, 224-458-8, Fugu Toxin, CHEMBL507974, TTX, (1R,5R,6R,7R,9S,11S,12S,13S,14S)-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 (non-preferred name), tettrodotoxin, UNII-3KUM2721U9, CCRIS 9328, HSDB 3543, 9SR, EINECS 224-458-8, BRN 0049176, TETRODOTOXIN [MI], TETRODOTOXIN [INN], Tetrodotoxin - citrate free, 4-27-00-08206 (Beilstein Handbook Reference), TETRODOTOXIN [WHO-DD], SCHEMBL6406675, SCHEMBL29352502, MSK9101, CFMYXEVWODSLAX-QOZOJKKESA-N, BDBM50344821, FT29063, 5,9:7,10a-Dimethano-10ah-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol, octahydro-12-(hydroxymethyl)-2-imino-, (4R-(4alpha,4aalpha,5alpha,7alpha,9alpha,10alpha,10abeta,11S*,12S*))-, 10-hydroxymethyl-5-imino-(2S)-12,13-dioxa-4,6-diazatetracyclo[7.3.1.13,11.03,8]tetradecane-1,2,7,10,14-pentaol, 10-hydroxymethyl-5-imino-(2S)-12,13-dioxa-4,6-diazatetracyclo[7.3.1.13,11.03,8]tetradecane-1,2,7,10,14-pentaolCitrate, 5,9:7,10a-Dimethano-10aH-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol, octahydro-12-(hydroxymethyl)-2-imino-, (4R,4aR,5R,7S,9S,10S,10aR,11S,12S)-
Theoretical properties:
molecular_formula: C11H17N3O8
molecular_weight: 319.27 g/mol
exact_mass: 319.10156451 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 8
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 1
heavy_atom_count: 22
topological_polar_surface_area: 190 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
melting_point: 225 °C (decomposes)
solubility: Soluble in dilute acetic acid; slightly soluble in dry alcohol, ether; practically insoluble in other organic solvents
Descriptions:
chebi: An iminium ion resulting from the protonation of the imine group of tetrodotoxin; major species at pH 7.3.
chembl: TETRODOTOXIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Tetrodotoxin (TTX) is a potent neurotoxin. Its name derives from Tetraodontiformes, an order that includes pufferfish, porcupinefish, ocean sunfish, and triggerfish; several of these species carry the toxin. Although tetrodotoxin was discovered in these fish, it is found in several other animals (e.g., in blue-ringed octopuses, rough-skinned newts, and moon snails). It is also produced by certain infectious or symbiotic bacteria like Pseudoalteromonas, Pseudomonas, and Vibrio as well as other species found in symbiotic relationships with animals and plants.
Although it produces thousands of intoxications annually and several deaths, it has shown efficacy for the treatment of cancer-related pain in phase II and III clinical trials.
Tetrodotoxin is a sodium channel blocker. It inhibits the firing of action potentials in neurons by binding to the voltage-gated sodium channels in nerve cell membranes and blocking the passage of sodium ions (responsible for the rising phase of an action potential) into the neuron. This prevents the nervous system from carrying messages and thus muscles from contracting in response to nervous stimulation.
Its mechanism of action – selective blocking of the sodium channel – was shown definitively in 1964 by Toshio Narahashi and John W. Moore at Duke University, using the sucrose gap voltage clamp technique.