Vamidothion (CED0023747)

Record Information

Version

1.0

Creation Date

2016-05-19 02:37:31 UTC

Update Date

2026-08-24 18:02:00 UTC

Accession Number

CHEM008079

Identification

Common Name

Vamidothion

Class

Small Molecule

Description

Vamidothion is an organic compound with the chemical formula C8H18NO4PS2 and an average molecular weight of 287.33 g/mol. Vamidothion belongs to the carboxylic acid derivatives, a subclass of carboxylic acids and derivatives within the organic compounds. This substance has been identified in three recorded sources, including drinking water and water supply (drinking water), as well as food, food processing, and cookware, specifically in the preparation of malt and molasses and the treatment of molasses. The recorded exposure route for this compound is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dimethyl S-(2-(1-methylcarbamoylethylthio)ethyl) phosphorothiolate	ChEBI
O,O-Dimethyl S-(2-(1-methylcarbamoylethylthio)ethyl) phosphorothioate	ChEBI
O,O-Dimethyl S-(2-{[1-methyl-2-(methylamino)-2-oxoethyl]sulfanyl}ethyl) thiophosphate	ChEBI
Vamidoate	ChEBI
Dimethyl S-(2-(1-methylcarbamoylethylthio)ethyl) phosphorothiolic acid	Generator
O,O-Dimethyl S-(2-(1-methylcarbamoylethylthio)ethyl) phosphorothioic acid	Generator
O,O-Dimethyl S-(2-{[1-methyl-2-(methylamino)-2-oxoethyl]sulfanyl}ethyl) thiophosphoric acid	Generator
O,O-Dimethyl S-(2-{[1-methyl-2-(methylamino)-2-oxoethyl]sulphanyl}ethyl) thiophosphate	Generator
O,O-Dimethyl S-(2-{[1-methyl-2-(methylamino)-2-oxoethyl]sulphanyl}ethyl) thiophosphoric acid	Generator
Vamidoic acid	Generator
2-(2-Dimethoxyphosphorylsulphanylethylsulphanyl)-N-methylpropanamide	Generator
Kilval	MeSH
Vamidothion	MeSH
O,O-Dimethyl S-(2-(1-methylcarbamoylethylthio)ethyl)phosphorothioate	MeSH

Chemical Formula

C₈H₁₈NO₄PS₂

Average Molecular Mass

287.330 g/mol

Monoisotopic Mass

287.041 g/mol

CAS Registry Number

2275-23-2

IUPAC Name

2-({2-[(dimethoxyphosphoryl)sulfanyl]ethyl}sulfanyl)-N-methylpropanimidic acid

Traditional Name

2-({2-[(dimethoxyphosphoryl)sulfanyl]ethyl}sulfanyl)-N-methylpropanimidic acid

SMILES

COP(=O)(OC)SCCSC(C)C(O)=NC

InChI Identifier

InChI=1S/C8H18NO4PS2/c1-7(8(10)9-2)15-5-6-16-14(11,12-3)13-4/h7H,5-6H2,1-4H3,(H,9,10)

InChI Key

LESVOLZBIFDZGS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as secondary carboxylic acid amides. Secondary carboxylic acid amides are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Secondary carboxylic acid amides

Alternative Parents

Substituents

Secondary carboxylic acid amide
Dialkylthioether
Sulfenyl compound
Thioether
Organothiophosphorus compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic thiophosphate (CHEBI:38990 )
organothiophosphate insecticide (CHEBI:38990 )
Organophosphorus insecticides (C18666 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.18 g/L	ALOGPS
logP	0.41	ALOGPS
logP	-1.5	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2.5	ChemAxon
pKa (Strongest Basic)	12.56	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.12 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	69.8 m³·mol⁻¹	ChemAxon
Polarizability	28.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1970000000-74fa153cb2f332ce497b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000j-9810000000-24be2cb8948c071a082a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-029l-9700000000-d53905c42abfa681cd3f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014u-0970000000-391f81db433608b2effa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uy0-5950000000-0300eddfdf7a86417fda	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00sr-8950000000-829c9d52f218ff312a39	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
20.0	Log mg/kg	[10:36]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
115	Drinking water	Drinking water & water supply	Not Available
546	Molasses And Treatment Of Molasses	Food, food processing & cookware	Not Available
547	Preparation Of Malt	Food, food processing & cookware	Not Available
583	Anchoring Equipment	Marine, shipping & aquaculture	Not Available
598	Fertiliser Distributors	Agriculture & land management	Not Available
607	Rodenticides(1)	Agriculture & land management	Not Available
608	Rodenticides	Agriculture & land management	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Acetylcholinesterase	P07140	Drosophila melanogaster	Predicted (SEA)	1.79053
Click to view 3D structure	Aminopeptidase N	P04825	Escherichia coli (strain K12)	Predicted (SEA)	11.7552
Click to view 3D structure	Glutamine synthetase	P0A9C5	Escherichia coli K-12	Predicted (SEA)	18.7617
Click to view 3D structure	S-methylmethionine--homocysteine S-methyltransferase BHMT2	Q9H2M3	Humans	Predicted (SEA)	16.504
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	6876.42
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	5745.58
Click to view 3D structure	Aldo-keto reductase family 1 member C3	P42330	Humans	Predicted (SEA)	4558.23
Click to view 3D structure	Ribose-5-phosphate isomerase B	P9WKD7	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	11.4438
Click to view 3D structure	UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q5HMD9	Staphylococcus epidermidis (strain ATCC 35984 / RP62A)	Predicted (SEA)	90.1494
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	6666.93
Click to view 3D structure	GIM-1 protein	Q704V1	Pseudomonas aeruginosa	Predicted (SEA)	527.973
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	6793.51
Click to view 3D structure	Aminopeptidase N	P15145	Sus scrofa	Predicted (SEA)	2265.8
Click to view 3D structure	6-phosphogluconolactonase	Q9GRG6	Trypanosoma brucei	Predicted (SEA)	12.923
Click to view 3D structure	Gamma-glutamyl hydrolase	Q92820	Humans	Predicted (SEA)	88.3589
Click to view 3D structure	Prostaglandin G/H synthase 1	P05979	Ovis aries	Predicted (SEA)	5778.28
Click to view 3D structure	Metabotropic glutamate receptor 6	P35349	Rattus norvegicus	Predicted (SEA)	1513.0
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	6978.09
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	6858.91
Click to view 3D structure	Farnesyl synthetase, putative	Q964Q8	Trypanosoma cruzi	Predicted (SEA)	132.889
Click to view 3D structure	Aldo-keto reductase family 1 member C2	P52895	Humans	Predicted (SEA)	4353.41
Click to view 3D structure	D-alanyl-D-alanine dipeptidase	Q06241	Enterococcus faecium	Predicted (SEA)	117.63
Click to view 3D structure	Fructose-bisphosphate aldolase, glycosomal	P07752	Trypanosoma brucei brucei	Predicted (SEA)	6.22794
Click to view 3D structure	Metabotropic glutamate receptor 4	P31423	Rattus norvegicus	Predicted (SEA)	3534.59
Click to view 3D structure	Matrix metalloproteinase-9	P14780	Humans	Predicted (SEA)	7133.25