Molecule

Tetrodotoxin

AlkaPlorer ID: AK023401

Synonym: None

IUPAC Name: (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

Structure

SMILES: N=C1N[C@H](O)[C@H]2[C@H]3O[C@]4(O)O[C@@H]([C@@H](O)[C@@]2(N1)[C@@H]4O)[C@]3(O)CO

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-QOZOJKKESA-N

Reference

Bacterial Production of Tetrodotoxin and Anhydrotetrodotoxin

PubChem CID: 11174599

LOTUS: LTS0035190

NPASS: NPC68327

{

NPAtlas: NPA024768

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Tadehagi triquetrum	Tadehagi	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Androstachys johnsonii	Androstachys	Picrodendraceae	Malpighiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Pseudomonas sp.	Pseudomonas	Pseudomonadaceae	Pseudomonadales	Gammaproteobacteria	Pseudomonadota	None	Bacteria
Bistorta affinis	Bistorta	Polygonaceae	Caryophyllales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Boehmeria excelsa	Boehmeria	Urticaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Geranium onoei	Geranium	Geraniaceae	Geraniales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Cestrum euanthes	Cestrum	Solanaceae	Solanales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Neopicrorhiza scrophulariiflora	Neopicrorhiza	Plantaginaceae	Lamiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Plagiorhegma dubium	Plagiorhegma	Berberidaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Streptomyces cyanogenus	Streptomyces	Streptomycetaceae	Kitasatosporales	Actinomycetes	Actinomycetota	None	Bacteria
Streptomyces sannurensis	Streptomyces	Streptomycetaceae	Kitasatosporales	Actinomycetes	Actinomycetota	None	Bacteria
Alternaria eichhorniae	Alternaria	Pleosporaceae	Pleosporales	Dothideomycetes	Ascomycota	Fungi	Eukaryota
Viguiera schultzii	Viguiera	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 319.2700000000001

TPSA？: 187.75

MolLogP？: -5.310129999999995

Number of H-Donors: 9

Number of H-Acceptors: 9

RingCount: 5

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Cavia porcellus	Heart	Inhibition	nan	%	10.1021/jm800100z
Cavia porcellus	Heart	Inhibition	nan	%	10.1021/jm900296e
Homo sapiens	A549	Activity	25.0	%	10.1016/j.bmc.2019.115300
Homo sapiens	A549	Activity	nan	None	10.1016/j.bmc.2019.115300
Homo sapiens	MDA-MB-231	Inhibition	31.5	%	10.1016/j.bmc.2018.04.003
Homo sapiens	MDA-MB-231	MNTD	30.0	uM	10.1016/j.bmc.2018.04.003
Homo sapiens	NCI-H460	Activity	25.0	%	10.1016/j.bmc.2019.115300
Homo sapiens	NCI-H460	Activity	nan	None	10.1016/j.bmc.2019.115300
Homo sapiens	Sodium channel protein type I alpha subunit	IC50	4.1	nM	10.1021/acs.jmedchem.8b01906
Homo sapiens	Sodium channel protein type I alpha subunit	IC50	30.0	nM	10.1021/jm3011433
Homo sapiens	Sodium channel protein type II alpha subunit	Activity	14.0	%	10.1016/j.bmcl.2017.01.054
Homo sapiens	Sodium channel protein type II alpha subunit	Activity	22.0	%	10.1016/j.bmcl.2017.01.054
Homo sapiens	Sodium channel protein type II alpha subunit	Activity	24.0	%	10.1016/j.bmcl.2017.01.054
Homo sapiens	Sodium channel protein type II alpha subunit	IC50	14.0	nM	10.1021/acs.jmedchem.8b01906
Homo sapiens	Sodium channel protein type II alpha subunit	IC50	30.0	nM	10.1021/jm3011433
Homo sapiens	Sodium channel protein type III alpha subunit	IC50	5.3	nM	10.1021/acs.jmedchem.8b01906
Homo sapiens	Sodium channel protein type III alpha subunit	IC50	30.0	nM	10.1021/jm3011433
Homo sapiens	Sodium channel protein type IV alpha subunit	IC50	7.6	nM	10.1021/acs.jmedchem.8b01906
Homo sapiens	Sodium channel protein type IV alpha subunit	IC50	25.0	nM	None
Homo sapiens	Sodium channel protein type IV alpha subunit	IC50	30.0	nM	10.1021/jm3011433
Homo sapiens	Sodium channel protein type IX alpha subunit	IC50	6.0	nM	10.1016/j.bmcl.2011.04.088
Homo sapiens	Sodium channel protein type IX alpha subunit	IC50	25.0	nM	None
Homo sapiens	Sodium channel protein type IX alpha subunit	IC50	30.0	nM	10.1021/jm3011433
Homo sapiens	Sodium channel protein type IX alpha subunit	Inhibition	nan	%	10.1016/j.bmcl.2017.01.054
Homo sapiens	Sodium channel protein type V alpha subunit	IC50	30.0	nM	10.1021/jm3011433
Homo sapiens	Sodium channel protein type V alpha subunit	IC50	1000.0	nM	10.1021/acs.jmedchem.8b01906
Homo sapiens	Sodium channel protein type V alpha subunit	Inhibition	79.0	%	10.1021/jm800100z
Homo sapiens	Sodium channel protein type V alpha subunit	Inhibition	79.0	%	10.1021/jm900296e
Homo sapiens	Sodium channel protein type V alpha subunit	Inhibition	87.0	%	10.1021/jm800100z
Homo sapiens	Sodium channel protein type V alpha subunit	Inhibition	87.0	%	10.1021/jm900296e
Homo sapiens	Sodium channel protein type V alpha subunit	Inhibition	95.0	%	10.1016/j.bmc.2018.04.003
Homo sapiens	Sodium channel protein type VII alpha subunit	IC50	36.0	nM	10.1021/acs.jmedchem.8b01906
Homo sapiens	Sodium channel protein type VIII alpha subunit	IC50	2.3	nM	10.1021/acs.jmedchem.8b01906
Homo sapiens	Sodium channel protein type VIII alpha subunit	IC50	30.0	nM	10.1021/jm3011433
Homo sapiens	Sodium channel protein type VIII alpha subunit	Inhibition	nan	%	10.1016/j.bmcl.2017.01.054
Homo sapiens	Sodium channel protein type X alpha subunit	IC50	30.0	nM	10.1021/jm3011433
Homo sapiens	Sodium channel protein type X alpha subunit	IC50	30000.0	nM	10.1021/acs.jmedchem.8b01906
Homo sapiens	Sodium channel protein type XI alpha subunit	IC50	30.0	nM	10.1021/jm3011433
Homo sapiens	Sodium channel protein type XI alpha subunit	IC50	30000.0	nM	10.1021/acs.jmedchem.8b01906
Homo sapiens	U-87 MG	Activity	nan	None	10.1016/j.bmc.2019.115300
Mus musculus	Sodium channel protein type 8 subunit alpha	IC50	6.0	nM	None
Oryctolagus cuniculus	Stomach	Activity	nan	None	10.1016/j.ejmech.2007.04.012
Periplaneta americana	Voltage-gated sodium channel Nav1 alpha subunit	Inhibition	nan	%	10.1124/mol.110.070540
Rattus norvegicus	Atrium	Inhibition	64.0	%	10.1021/jm800100z
Rattus norvegicus	Atrium	Inhibition	64.0	%	10.1021/jm900296e
Rattus norvegicus	Cortical neurone	Activity	77.0	%	10.1021/acs.jmedchem.6b00478
Rattus norvegicus	Ileum	Inhibition	nan	%	10.1016/j.ejmech.2016.01.021
Rattus norvegicus	Rattus norvegicus	ED	1.0	ug/kg	10.1021/acs.jmedchem.8b01906
Rattus norvegicus	Rattus norvegicus	ED	6.0	ug/kg	10.1021/acs.jmedchem.8b01906
Rattus norvegicus	Rattus norvegicus	Inhibition	100.0	%	10.1021/jm401881q
Rattus norvegicus	Sodium channel protein type I alpha subunit	IC50	10.0	nM	None
Rattus norvegicus	Sodium channel protein type II alpha subunit	IC50	4.0	nM	10.1021/jm980124a
Rattus norvegicus	Sodium channel protein type II alpha subunit	IC50	10.0	nM	None
Rattus norvegicus	Sodium channel protein type II alpha subunit	IC50	14.0	nM	10.1021/jm00028a010
Rattus norvegicus	Sodium channel protein type III alpha subunit	IC50	15.0	nM	None
Rattus norvegicus	Sodium channel protein type V alpha subunit	IC50	2000.0	nM	None
Rattus norvegicus	Sodium channel protein type X alpha subunit	IC50	50000.0	nM	None
Rattus norvegicus	Sodium channel protein type XI alpha subunit	IC50	1000.0	nM	None
Rattus norvegicus	Voltage-gated sodium channel	Kd	1.8	nM	10.1021/acs.jnatprod.9b00178
None	ADMET	Activity	nan	None	10.1021/acs.jnatprod.2c00588
None	ADMET	LD50	0.01	mg.kg-1	10.1021/acs.jnatprod.9b00178
None	NON-PROTEIN TARGET	Activity	88.0	%	10.1016/j.ejmech.2015.12.043
None	Unchecked	EC50	1.9	nM	10.1021/acs.jnatprod.9b00178
None	Unchecked	EC50	2.1	nM	10.1021/np401097n
None	Unchecked	ED50	4.1	nM	10.1021/acs.jnatprod.9b00178
None	Unchecked	IC50	1.69	nM	10.1021/acs.jnatprod.1c00978
None	Unchecked	IC50	4.93	nM	10.1021/acs.jnatprod.1c00978
None	Unchecked	Inhibition	nan	%	10.1016/j.bmcl.2017.01.054
None	Unchecked	Inhibition	nan	%	10.1021/acs.jnatprod.9b00178
None	Unchecked	Inhibition	nan	%	10.1021/np401097n
None	Unchecked	Ratio IC50	1.0	None	10.1021/acs.jmedchem.8b01906
None	Unchecked	Ratio IC50	27.0	None	10.1021/acs.jmedchem.8b01906
None	Unchecked	Ratio IC50	800.0	None	10.1021/acs.jmedchem.8b01906