dimethyl ({2-[1-(methylcarbamoyl)ethanesulfinyl]ethyl}sulfanyl)phosphonate

• ChemBase ID: 179556
• Molecular Formular: C8H18NO5PS2
• Molecular Mass: 303.335981
• Monoisotopic Mass: 303.03640131
• SMILES: C(C(=O)NC)(S(=O)CCSP(=O)(OC)OC)C
• Canonical SMILES: CNC(=O)C(S(=O)CCSP(=O)(OC)OC)C
• InChI: InChI=1S/C8H18NO5PS2/c1-7(8(10)9-2)17(12)6-5-16-15(11,13-3)14-4/h7H,5-6H2,1-4H3,(H,9,10)
• InChIKey: DOAIKHBMDHDGSV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl ({2-[1-(methylcarbamoyl)ethanesulfinyl]ethyl}sulfanyl)phosphonate
• IUPAC Traditional name: dimethyl {2-[1-(methylcarbamoyl)ethanesulfinyl]ethyl}sulfanylphosphonate
• Synonyms: Phosphorothioic Acid O,O-Dimethyl S-[2-[[1-Methyl-2-(methylamino)-2-oxoethyl]sulfinyl]ethyl] Ester; Vamidothion Sulfoxide

Database IDs

• CAS Number: 20300-00-9
• PubChem SID: 164235466
• PubChem CID: 16212160

CALCULATED PROPERTIES

• Acid pKa: 9.309144
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.127199
• LogD (pH = 7.4): -1.1324487
• Log P: -1.1271317
• Molar Refractivity: 70.7611 cm^3
• Polarizability: 28.263664 Å^3
• Polar Surface Area: 81.7 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V756500

Vamidothion sulfoxide is a metabolite of Vamidothion, a phosphorothioic insecticide for apples and potatoes.

REFERENCES

• El-Oshar, M.A., et al.: J. Agric. Food Chem., 35, 138 (1987)