(2R)-2-amino-3-{[(Z)-1,2-dichloroethenyl]sulfanyl}propanoic acid

• ChemBase ID: 167165
• Molecular Formular: C5H7Cl2NO2S
• Molecular Mass: 216.08558
• Monoisotopic Mass: 214.95745483
• SMILES: C(=C(\SC[C@H](N)C(=O)O)/Cl)/Cl
• Canonical SMILES: N[C@H](C(=O)O)CS/C(=C/Cl)/Cl
• InChI: InChI=1S/C5H7Cl2NO2S/c6-1-4(7)11-2-3(8)5(9)10/h1,3H,2,8H2,(H,9,10)/b4-1+/t3-/m0/s1
• InChIKey: PJIHCWJOTSJIPQ-AGFFZDDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-{[(Z)-1,2-dichloroethenyl]sulfanyl}propanoic acid
• IUPAC Traditional name: C5H7cl2NO2S
• Synonyms: DCVC; S-1,2-Dichlorovinyl-L-cysteine; S-(1,2-Dichloroethenyl)-L-cysteine; NSC 15830; 3-[(1,2-Dichlorovinyl)thio]-L-alanine

Database IDs

• CAS Number: 627-72-5
• PubChem SID: 162261298
• PubChem CID: 6433207

CALCULATED PROPERTIES

• Acid pKa: 1.5692477
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.7094342
• LogD (pH = 7.4): -0.71842057
• Log P: -0.709446
• Molar Refractivity: 55.6184 cm^3
• Polarizability: 18.679783 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol

DETAILS

Toronto Research Chemicals - D435945

A mutagenic and nephrotoxic metabolite of trichloroethylene.

REFERENCES

• Barshteyn, N. et al.: Chem. Res. Toxicol. 22, 1629 (2009)