NP-MRD: Showing NP-Card for fosthiazate (NP0216136)

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Record Information

Version

2.0

Created at

2022-09-05 15:58:52 UTC

Updated at

2022-09-05 15:58:52 UTC

NP-MRD ID

NP0216136

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fosthiazate

Description

Fosthiazate, also known as nemathorin or fosthiazic acid, belongs to the class of organic compounds known as thiazolidines. These are heterocyclic compounds containing a five-member saturated aliphatic ring with one nitrogen atom, one sulfur atom, three carbon atoms. Fosthiazate is possibly neutral. Fosthiazate is a potentially toxic compound. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. fosthiazate is found in Capparis spinosa. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04251301022D          

 16 16  0  0  0  0            999 V2000
    1.3928    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    2.7643    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    4.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6697    2.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    3.3682    0.0000 C   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  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216136

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOP(=O)(SC(C)CC)N1CCSC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H18NO3PS2/c1-4-8(3)16-14(12,13-5-2)10-6-7-15-9(10)11/h8H,4-7H2,1-3H3

> <INCHI_KEY>
DUFVKSUJRWYZQP-UHFFFAOYSA-N

> <FORMULA>
C9H18NO3PS2

> <MOLECULAR_WEIGHT>
283.348

> <EXACT_MASS>
283.046571339

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.082058195615225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl (butan-2-ylsulfanyl)(2-oxo-1,3-thiazolidin-3-yl)phosphinate

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
2.437769499666667

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
46.61

> <JCHEM_REFRACTIVITY>
70.6791

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fosthiazate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-13         0                                  
HETATM    1  O   UNK     0       2.600   3.620   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0       1.060   3.620   0.000  0.00  0.00           P+0
HETATM    3  S   UNK     0       1.060   5.160   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.393   7.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.727   5.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.061   5.930   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.060   2.080   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0       0.290  -0.290   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.480   3.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.250   4.954   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.480   6.287   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   14                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    8   11   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
(RS)-S-Sec-butyl-O-ethyl-2-oxo-1,3-thiazolidin-3-ylphosphonothioate	ChEBI
Nemathorin	ChEBI
S-Sec-butyl O-ethyl (2-oxo-1,3-thiazolidin-3-yl)phosphonothioate	ChEBI
(RS)-S-Sec-butyl-O-ethyl-2-oxo-1,3-thiazolidin-3-ylphosphonothioic acid	Generator
S-Sec-butyl O-ethyl (2-oxo-1,3-thiazolidin-3-yl)phosphonothioic acid	Generator
Fosthiazic acid	Generator

Chemical Formula

C₉H₁₈NO₃PS₂

Average Mass

283.3480 Da

Monoisotopic Mass

283.04657 Da

IUPAC Name

ethyl (butan-2-ylsulfanyl)(2-oxo-1,3-thiazolidin-3-yl)phosphinate

Traditional Name

fosthiazate

CAS Registry Number

Not Available

SMILES

CCOP(=O)(SC(C)CC)N1CCSC1=O

InChI Identifier

InChI=1S/C9H18NO3PS2/c1-4-8(3)16-14(12,13-5-2)10-6-7-15-9(10)11/h8H,4-7H2,1-3H3

InChI Key

DUFVKSUJRWYZQP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Capparis spinosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiazolidines. These are heterocyclic compounds containing a five-member saturated aliphatic ring with one nitrogen atom, one sulfur atom, three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Thiazolidines

Direct Parent

Thiazolidines

Alternative Parents

Substituents

Thiazolidine
Carbonic acid derivative
Azacycle
Sulfenyl compound
Organothiophosphorus compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organic phosphonate (CHEBI:38692 )
phosphonic ester (CHEBI:38692 )
organothiophosphate insecticide (CHEBI:38692 )
Nematicides (C18402 )

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	1.51	ALOGPS
logP	2.44	ChemAxon
logS	-1.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.68 m³·mol⁻¹	ChemAxon
Polarizability	28.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C18402

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91758

PDB ID

Not Available

ChEBI ID

38692

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for fosthiazate (NP0216136)

MOL for NP0216136 (fosthiazate)

3D MOL for NP0216136 (fosthiazate)

3D SDF for NP0216136 (fosthiazate)

3D-SDF for NP0216136 (fosthiazate)

PDB for NP0216136 (fosthiazate)

3D PDB for NP0216136 (fosthiazate)

SMILES for NP0216136 (fosthiazate)

INCHI for NP0216136 (fosthiazate)

Structure for NP0216136 (fosthiazate)

3D Structure for NP0216136 (fosthiazate)