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.
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2D Structure
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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
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Nav1.1 Hs Channel blocker Pore blocker - - 1x10-8
Conc range: 1x10-8 M
Nav1.1 Rn Channel blocker Pore blocker 8.0 pKd - 11
pKd 8.0 [11]
Voltage: -100.0 mV
Nav1.5 Rn Channel blocker Pore blocker 5.8 pKd - 5,13
pKd 5.8 (Kd 1.52x10-6 M) [5,13]
Voltage: -80.0 mV
Nav1.6 Rn Channel blocker Pore blocker 9.0 pIC50 - 7
pIC50 9.0 (IC50 1x10-9 M) [7]
Voltage: -130.0 mV
Nav1.3 Hs Channel blocker Pore blocker 8.4 pIC50 - 4
pIC50 8.4 (IC50 4x10-9 M) [4]
Nav1.7 Rn Channel blocker Pore blocker 8.4 pIC50 - 9
pIC50 8.4 [9]
Voltage: -100.0 mV
Nav1.4 Rn Channel blocker Pore blocker 8.3 pIC50 - 12
pIC50 8.3 [12]
Voltage: -120.0 mV
Nav1.6 Mm Channel blocker Pore blocker 8.2 pIC50 - 10
pIC50 8.2 [10]
Voltage: -60.0 mV
Nav1.2 Rn Channel blocker Pore blocker 8.0 pIC50 - 2
pIC50 8.0 (IC50 1.12x10-8 M) [2]
Voltage: -120.0 mV
Nav1.4 Hs Channel blocker Pore blocker 7.6 pIC50 - 3
pIC50 7.6 (IC50 2.5x10-8 M) [3]
Voltage: -120.0 mV
Nav1.7 Hs Channel blocker Pore blocker 7.6 pIC50 - 8
pIC50 7.6 (IC50 2.45x10-8 M) [8]
Voltage: -100.0 mV
Nav1.9 Rn Channel blocker Pore blocker 4.4 pIC50 - 6
pIC50 4.4 (IC50 3.9x10-5 M) [6]
Voltage: -120.0 mV
Nav1.8 Rn Channel blocker Pore blocker 4.2 pIC50 - 1
pIC50 4.2 (IC50 5.96x10-5 M) [1]
Voltage: -60.0 mV
Ligand mentioned in the following text fields