NP-MRD: Showing NP-Card for (1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol (NP0172896)

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Record Information

Version

2.0

Created at

2022-09-03 09:55:44 UTC

Updated at

2022-09-03 09:55:45 UTC

NP-MRD ID

NP0172896

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

Description

Tetrodotoxin, also known as tarichatoxin or BJT 1, belongs to the class of organic compounds known as tetrodotoxins. Tetrodotoxins are compounds structurally characterized by the presence of the tetrodotoxin skeleton, which is based on 5,7-(epoxymethanooxy)quinazolin-10-olate moiety. Tetrodotoxin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol was first documented in 2022 (PMID: 36043704). Based on a literature review a significant number of articles have been published on tetrodotoxin (PMID: 36041513) (PMID: 36037599) (PMID: 36006238) (PMID: 35995562) (PMID: 35994072) (PMID: 35963299).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
   -4.9393   -1.4007   -0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205   -1.0959    0.2139 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0552   -0.9622   -0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054   -1.2253   -1.2697 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055   -1.0413   -1.6125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7074   -2.2463   -2.2367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407   -0.8666   -0.4104 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0676   -0.2400   -0.7985 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8055    1.0453   -1.2800 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2669    1.8745   -0.3138 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1607    3.1482   -0.8639 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625    1.9759    0.8252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3228    0.7455    1.4113 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0879    0.0024    1.8208 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4794   -1.3428    2.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8963   -0.0205    0.6737 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1787   -0.5424    1.0320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    1.3881    0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9824    1.3986   -0.9054 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226   -0.1020    0.3508 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4777   -1.2988    0.8428 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955    0.7423   -0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898    0.0897   -1.1534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1254   -1.5781   -2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573   -0.2555   -2.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6449   -2.9061   -1.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064   -1.8689    0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5078   -0.8182   -1.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1294    3.8547   -0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0183    0.9090    2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523    0.3382    2.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1991   -1.8538    2.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446   -0.6052    2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4121    2.0533    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6932    2.0562   -1.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9906   -1.1096    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556    1.7029   -0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246    0.9506    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7963   -0.8946   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 20  1  0
 20 21  1  1
 20 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  1  6
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  3 17  1  0
 16 17  1  1
 16 14  1  0
 14 15  1  0
 16 18  1  0
 18 19  1  0
  8 20  1  0
 16  7  1  0
 14 13  1  0
 18 10  1  0
 23 39  1  0
 22 37  1  0
 22 38  1  0
 21 36  1  0
 13 30  1  1
 11 29  1  0
  8 28  1  6
  7 27  1  1
  5 25  1  6
  6 26  1  0
  4 24  1  0
  2  1  1  0
 17 33  1  0
 14 31  1  1
 15 32  1  0
 18 34  1  1
 19 35  1  0
M  END


  Mrv1652309032211552D          

 22 25  0  0  1  0            999 V2000
   -0.9519   -0.2832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956    0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372    0.8873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944    1.2979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6648    2.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547    0.7613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9967    1.2231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3817    0.4912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -0.4164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7992   -1.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488   -0.3908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9813    0.3039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0830   -0.0056    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2783   -0.8071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2456   -0.1290    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4591   -0.4822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8133   -0.7927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6414   -1.5996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8549    1.1707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6427    1.4158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331    1.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4246    2.5333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  6  0  0  0
  2 16  1  0  0  0  0
 15 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  1  0  0  0
 12 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@]1(O)[C@H]2O[C@@]3(O)O[C@@H]1[C@@H]1[C@@H](O)NC(=N)N[C@]1([C@H]2O)[C@@H]3O

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C11H17N3O8

> <MOLECULAR_WEIGHT>
319.27

> <EXACT_MASS>
319.101564519

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.06048425826203

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R,6R,7R,9S,11S,12R,13S,14S)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1^{7,11}.0^{1,6}]tetradecane-5,9,12,13,14-pentol

> <ALOGPS_LOGP>
-2.64

> <JCHEM_LOGP>
-4.594978829194681

> <ALOGPS_LOGS>
-0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.913761231261727

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.338586452684822

> <JCHEM_PKA_STRONGEST_BASIC>
9.197726065005597

> <JCHEM_POLAR_SURFACE_AREA>
187.75

> <JCHEM_REFRACTIVITY>
75.26329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6R,7R,9S,11S,12R,13S,14S)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1^{7,11}.0^{1,6}]tetradecane-5,9,12,13,14-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  N   UNK     0      -1.777  -0.529   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.365   0.087   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.256   1.656   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.109   2.423   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.241   3.957   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.342   1.421   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.727   2.283   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.446   0.917   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.864  -0.777   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.225  -2.274   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.438  -0.729   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.565   0.567   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.888  -0.010   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.253  -1.507   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.325  -0.241   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.857  -0.900   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.385  -1.480   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.064  -2.986   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.329   2.185   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.800   2.643   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.662   3.689   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.526   4.729   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   17                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16   17                                             
CONECT   16   15    2                                                       
CONECT   17   15    9   18                                                  
CONECT   18   17                                                            
CONECT   19   12    7   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
Babylonia japonica toxin 1	ChEBI
BJT 1	ChEBI
Fugu poison	ChEBI
Maculotoxin	ChEBI
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
Spheroidine	ChEBI
Tarichatoxin	ChEBI
Tetrodontoxin	ChEBI
Tetrodotoxine	ChEBI
TTX	ChEBI
Toxin, fugu	MeSH
Fugu toxin	MeSH
Tetradotoxin	MeSH

Chemical Formula

C₁₁H₁₇N₃O₈

Average Mass

319.2700 Da

Monoisotopic Mass

319.10156 Da

IUPAC Name

(1R,5R,6R,7R,9S,11S,12R,13S,14S)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1^{7,11}.0^{1,6}]tetradecane-5,9,12,13,14-pentol

Traditional Name

(1R,5R,6R,7R,9S,11S,12R,13S,14S)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1^{7,11}.0^{1,6}]tetradecane-5,9,12,13,14-pentol

CAS Registry Number

Not Available

SMILES

OC[C@@]1(O)[C@H]2O[C@@]3(O)O[C@@H]1[C@@H]1[C@@H](O)NC(=N)N[C@]1([C@H]2O)[C@@H]3O

InChI Identifier

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrodotoxins. Tetrodotoxins are compounds structurally characterized by the presence of the tetrodotoxin skeleton, which is based on 5,7-(epoxymethanooxy)quinazolin-10-olate moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Tetrodotoxins

Alternative Parents

Substituents

Tetrodotoxin-skeleton
Meta-dioxane
Hydropyrimidine
1,4,5,6-tetrahydropyrimidine
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
Guanidine
Orthocarboxylic acid derivative
Secondary alcohol
Alkanolamine
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Carboximidamide
Alcohol
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Primary alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

quinazoline alkaloid (CHEBI:9506 )
azatetracycloalkane (CHEBI:9506 )
oxatetracycloalkane (CHEBI:9506 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.6	ALOGPS
logP	-4.6	ChemAxon
logS	-0.42	ALOGPS
pKa (Strongest Acidic)	10.34	ChemAxon
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	187.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.26 m³·mol⁻¹	ChemAxon
Polarizability	28.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00055525

Chemspider ID

5291663

KEGG Compound ID

Not Available

BioCyc ID

CPD-19561

BiGG ID

Not Available

Wikipedia Link

Tetrodotoxin

METLIN ID

Not Available

PubChem Compound

6324668

PDB ID

Not Available

ChEBI ID

9506

Good Scents ID

rw1086261

References

General References

Sukhanova KY, Koirala A, Elmslie KS: Na_V1.9 current in muscle afferent neurons is enhanced by substances released during muscle activity. J Neurophysiol. 2022 Oct 1;128(4):739-750. doi: 10.1152/jn.00116.2022. Epub 2022 Aug 31. [PubMed:36043704 ]
Amano M, Takatani T, Sakayauchi F, Oi R, Sakakura Y: The brain of the wild toxic marine pufferfishes accumulates tetrodotoxin. Toxicon. 2022 Oct 30;218:1-7. doi: 10.1016/j.toxicon.2022.08.015. Epub 2022 Aug 27. [PubMed:36041513 ]
Li Y, Zhang L, Wang W, Liu Y, Sun D, Li H, Chen L: A review on natural products with cage-like structure. Bioorg Chem. 2022 Nov;128:106106. doi: 10.1016/j.bioorg.2022.106106. Epub 2022 Aug 24. [PubMed:36037599 ]
Melnikova DI, Magarlamov TY: An Overview of the Anatomical Distribution of Tetrodotoxin in Animals. Toxins (Basel). 2022 Aug 22;14(8):576. doi: 10.3390/toxins14080576. [PubMed:36006238 ]
Buckmaster PS, Reyes B, Kahn T, Wyeth M: Ventral hippocampal formation is the primary epileptogenic zone in a rat model of temporal lobe epilepsy. J Neurosci. 2022 Aug 19;42(39):7482-95. doi: 10.1523/JNEUROSCI.0429-22.2022. [PubMed:35995562 ]
Yaegashi Y, Kudo Y, Ueyama N, Onodera KI, Cho Y, Konoki K, Yotsu-Yamashita M: Isolation and Biological Activity of 9-epiTetrodotoxin and Isolation of Tb-242B, Possible Biosynthetic Shunt Products of Tetrodotoxin from Pufferfish. J Nat Prod. 2022 Sep 23;85(9):2199-2206. doi: 10.1021/acs.jnatprod.2c00588. Epub 2022 Aug 22. [PubMed:35994072 ]
Britto-Junior J, de Oliveira MG, Dos Reis Gati C, Campos R, Moraes MO, Moraes MEA, Monica FZ, Antunes E, De Nucci G: 6-NitroDopamine is an endogenous modulator of rat heart chronotropism. Life Sci. 2022 Oct 15;307:120879. doi: 10.1016/j.lfs.2022.120879. Epub 2022 Aug 10. [PubMed:35963299 ]
Nomura T, Hayakawa K, Sato N, Obinata T: Periodic Stretching of Cultured Myotubes Enhances Myofibril Assembly. Zoolog Sci. 2022 Aug;39(4). doi: 10.2108/zs220015. [PubMed:35960030 ]
Eid A, Mhatre-Winters I, Sammoura FM, Edler MK, von Stein R, Hossain MM, Han Y, Lisci M, Carney K, Konsolaki M, Hart RP, Bennett JW, Richardson JR: Effects of DDT on Amyloid Precursor Protein Levels and Amyloid Beta Pathology: Mechanistic Links to Alzheimer's Disease Risk. Environ Health Perspect. 2022 Aug;130(8):87005. doi: 10.1289/EHP10576. Epub 2022 Aug 10. [PubMed:35946953 ]
Walch E, Bilas A, Bebawy V, Lam A, Murphy TR, Sriram S, Fiacco TA: Contributions of Astrocyte and Neuronal Volume to CA1 Neuron Excitability Changes in Elevated Extracellular Potassium. Front Cell Neurosci. 2022 Jul 22;16:930384. doi: 10.3389/fncel.2022.930384. eCollection 2022. [PubMed:35936495 ]
He X, Wu H, Ye Y, Gong X, Bao B: Transcriptome analysis revealed gene expression feminization of testis after exogenous tetrodotoxin administration in pufferfish Takifugu flavidus. BMC Genomics. 2022 Aug 3;23(1):553. doi: 10.1186/s12864-022-08787-z. [PubMed:35922761 ]
Idrizaj E, Garella R, Nistri S, Squecco R, Baccari MC: Evidence that resistin acts on the mechanical responses of the mouse gastric fundus. Front Physiol. 2022 Jul 15;13:930197. doi: 10.3389/fphys.2022.930197. eCollection 2022. [PubMed:35910552 ]
Matthews RM, Bradley E, Griffin CS, Lim XR, Mullins ND, Hollywood MA, Lundy FT, McGarvey LP, Sergeant GP, Thornbury KD: Functional expression of Na(V)1.7 channels in freshly dispersed mouse bronchial smooth muscle cells. Am J Physiol Cell Physiol. 2022 Sep 1;323(3):C749-C762. doi: 10.1152/ajpcell.00011.2022. Epub 2022 Jul 25. [PubMed:35876287 ]
Wigenstam E, Artursson E, Bucht A, Thors L: Supplemental treatment to atropine improves the efficacy to reverse nerve agent induced bronchoconstriction. Chem Biol Interact. 2022 Sep 1;364:110061. doi: 10.1016/j.cbi.2022.110061. Epub 2022 Jul 22. [PubMed:35872047 ]
Holmuhamedov EL, Chakraborty P, Oberlin A, Liu X, Yousufuddin M, Shen WK, Terzic A, Jahangir A: Aging-associated susceptibility to stress-induced ventricular arrhythmogenesis is attenuated by tetrodotoxin. Biochem Biophys Res Commun. 2022 Oct 1;623:44-50. doi: 10.1016/j.bbrc.2022.07.040. Epub 2022 Jul 15. [PubMed:35870261 ]
Konrad DB, Ruhmann KP, Ando H, Hetzler BE, Strassner N, Houk KN, Matsuura BS, Trauner D: A concise synthesis of tetrodotoxin. Science. 2022 Jul 22;377(6604):411-415. doi: 10.1126/science.abn0571. Epub 2022 Jul 21. [PubMed:35862530 ]
Ballout J, Classen R, Richter K, Grau V, Diener M: Ionotropic P2X4 and P2X7 receptors in the regulation of ion transport across rat colon. Br J Pharmacol. 2022 Nov;179(21):4992-5011. doi: 10.1111/bph.15928. Epub 2022 Aug 5. [PubMed:35853139 ]
Chen K, Dai Y: Chronic exercise increases excitability of lamina X neurons through enhancement of persistent inward currents and dendritic development in mice. J Physiol. 2022 Aug;600(16):3775-3793. doi: 10.1113/JP283037. Epub 2022 Aug 2. [PubMed:35848453 ]
Suo R, Tanaka M, Oyama H, Kojima Y, Yui K, Sakakibara R, Nakahigashi R, Adachi M, Nishikawa T, Sugita H, Itoi S: Tetrodotoxins in the flatworm Planocera multitentaculata. Toxicon. 2022 Sep;216:169-173. doi: 10.1016/j.toxicon.2022.07.001. Epub 2022 Jul 16. [PubMed:35843466 ]
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LOTUS database [Link]

Showing NP-Card for (1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol (NP0172896)

MOL for NP0172896 ((1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol)

3D MOL for NP0172896 ((1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol)

3D SDF for NP0172896 ((1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol)

3D-SDF for NP0172896 ((1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol)

PDB for NP0172896 ((1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol)

3D PDB for NP0172896 ((1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol)

SMILES for NP0172896 ((1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol)

INCHI for NP0172896 ((1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol)

Structure for NP0172896 ((1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol)

3D Structure for NP0172896 ((1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol)