Tetrodotoxin

Details

• Internal ID: 38773411-1a3a-4604-923c-f0396c11c03a
• Taxonomy: Organoheterocyclic compounds > Diazanaphthalenes > Benzodiazines > Quinazolines > Tetrodotoxins
• 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
• SMILES (Canonical): C(C1(C2C3C(N=C(NC34C(C1OC(C4O)(O2)O)O)N)O)O)O
• SMILES (Isomeric): C([C@@]1([C@H]2[C@@H]3[C@H](N=C(N[C@@]34[C@@H]([C@@H]1O[C@]([C@H]4O)(O2)O)O)N)O)O)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-QOZOJKKESA-N
• Popularity: 13,058 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₇N₃O₈
• Molecular Weight: 319.27 g/mol
• Exact Mass: 319.10156451 g/mol
• Topological Polar Surface Area (TPSA): 190.00 Ų
• XlogP: -5.90
• Atomic LogP (AlogP): -5.52
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 1

Synonyms

• Tetrodotoxine
• Spheroidine
• Tarichatoxin
• Babylonia japonica toxin 1
• Tectin
• BJT 1
• Maculotoxin
• 4368-28-9
• Pft-1 toxin
• Tetrodontoxin
• Tetrodoxin
• UNII-3KUM2721U9
• Fugu poison
• CCRIS 9328
• HSDB 3543
• 3KUM2721U9
• EINECS 224-458-8
• BRN 0049176
• Tetradotoxin
• CHEMBL507974
• Fugu Toxin
• 4-27-00-08206 (Beilstein Handbook Reference)
• TTX
• 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*))-
• Toxin, Fugu
• (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)
• 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-
• 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)-
• (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
• CHEBI:9506
• DTXSID10881342
• tetrodotoxina
• tetrodotoxinum
• tettrodotoxin
• C11-H17-N3-O8
• 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-, (4R,4aR,5R,7S,9S,10S,10aR,11S,12S)-
• 9SR
• TETRODOTOXIN [MI]
• TETRODOTOXIN [INN]
• BJT-1
• TETRODOTOXIN [WHO-DD]
• SCHEMBL6406675
• DTXCID101022591
• BDBM50344821
• Q-100286
• (4R,4aR,5R,7S,9S,10S,10aR,11S,12S)-2-Amino-1,4,4a,5,9,10-hexahydro-12-(hydroxymethyl)-5,9:7,10a-dimethano-10aH-
• 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-(4ALPHA,4AALPHA,5ALPHA,7ALPHA,9ALPHA, 10ALPHA,10ABETA,11S*,12S*))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7923	79.23%
Caco-2	-	0.8727	87.27%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Lysosomes	0.5304	53.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9265	92.65%
OATP1B3 inhibitior	+	0.9440	94.40%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9772	97.72%
P-glycoprotein inhibitior	-	0.9118	91.18%
P-glycoprotein substrate	-	0.6812	68.12%
CYP3A4 substrate	-	0.5062	50.62%
CYP2C9 substrate	-	0.8117	81.17%
CYP2D6 substrate	-	0.8008	80.08%
CYP3A4 inhibition	-	0.9762	97.62%
CYP2C9 inhibition	-	0.8946	89.46%
CYP2C19 inhibition	-	0.8522	85.22%
CYP2D6 inhibition	-	0.9149	91.49%
CYP1A2 inhibition	-	0.8161	81.61%
CYP2C8 inhibition	-	0.7811	78.11%
CYP inhibitory promiscuity	-	0.9786	97.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6138	61.38%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.9776	97.76%
Skin irritation	-	0.7759	77.59%
Skin corrosion	-	0.9274	92.74%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7140	71.40%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.7048	70.48%
skin sensitisation	-	0.7522	75.22%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7838	78.38%
Acute Oral Toxicity (c)	III	0.5246	52.46%
Estrogen receptor binding	-	0.4742	47.42%
Androgen receptor binding	+	0.5466	54.66%
Thyroid receptor binding	+	0.7170	71.70%
Glucocorticoid receptor binding	+	0.6294	62.94%
Aromatase binding	+	0.6019	60.19%
PPAR gamma	+	0.6824	68.24%
Honey bee toxicity	-	0.7956	79.56%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.9714	97.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1845	P35498	Sodium channel protein type I alpha subunit	< 30 nM; 4.1 nM	IC50; IC50	PMID: 23121096; via Super-PRED
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	< 30 nM; 14 nM	IC50; IC50	PMID: 23121096; via Super-PRED
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	< 30 nM; 5.3 nM	IC50; IC50	PMID: 23121096; via Super-PRED
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	7.6 nM; < 30 nM	IC50; IC50	via Super-PRED; PMID: 23121096
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	18.6 nM; 6 nM; 6 nM; < 30 nM	IC50; IC50; IC50; IC50	via Super-PRED; PMID: 21570288; via Super-PRED; PMID: 23121096
CHEMBL5202	Q9UQD0	Sodium channel protein type VIII alpha subunit	2.3 nM; < 30 nM	IC50; IC50	via Super-PRED; PMID: 23121096
CHEMBL5167	Q9UI33	Sodium channel protein type XI alpha subunit	< 30 nM	IC50	PMID: 23121096

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.21%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.74%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	90.50%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.64%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.67%	91.11%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.31%	97.28%
CHEMBL221	P23219	Cyclooxygenase-1	83.88%	90.17%
CHEMBL2094135	Q96BI3	Gamma-secretase	81.49%	98.05%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.24%	94.00%

Plants that contains it

• Neopicrorhiza scrophulariiflora
• Tadehagi triquetrum

Cross-Links

• PubChem: 11174599
• NPASS: NPC68327
• ChEMBL: CHEMBL507974
• LOTUS: LTS0035190
• wikiData: Q76416754