(2R)-3-{[(Z)-1,2-dichloroethenyl]sulfanyl}-2-[(1-13C,2H3)acetamido]propanoic acid

• ChemBase ID: 159226
• Molecular Formular: C7H9Cl2NO3S
• Molecular Mass: 259.11491484
• Monoisotopic Mass: 257.97137435
• SMILES: C(=C(\SC[C@H](N[13C](=O)C)C(=O)O)/Cl)/Cl
• Canonical SMILES: Cl/C=C(/SC[C@@H](C(=O)O)N[13C](=O)C)\Cl
• InChI: InChI=1S/C7H9Cl2NO3S/c1-4(11)10-5(7(12)13)3-14-6(9)2-8/h2,5H,3H2,1H3,(H,10,11)(H,12,13)/b6-2+/t5-/m0/s1/i4+1
• InChIKey: LPPJGTSPIBSYQO-WCLCYVNSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-{[(Z)-1,2-dichloroethenyl]sulfanyl}-2-[(1-^1^3C,^2H₃)acetamido]propanoic acid
• IUPAC Traditional name: (2R)-3-{[(Z)-1,2-dichloroethenyl]sulfanyl}-2-[(1-^1^3C,^2H₃)acetamido]propanoic acid
• Synonyms: N-Acetyl-3-[(1,2-dichlorovinyl)thio]alanine-13C,d3; S-(1,2-Dichlorovinyl)-L-cysteine-13C,d3; 1,2-DCVMA-13C,d3; NA-1,2-DCVC-13C,d3; N-Acetyl-S-(1,2-dichloroethenyl)-L-cysteine-13C,d3

Database IDs

• PubChem SID: 162253361
• PubChem CID: 71312863

CALCULATED PROPERTIES

• Acid pKa: 3.4213445
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.69522935
• LogD (pH = 7.4): -2.0254953
• Log P: 1.3719261
• Molar Refractivity: 65.0622 cm^3
• Polarizability: 22.116808 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 91-93°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A173587

Labelled trichloroethylene metabolite

REFERENCES

• Werner, M., et al.: Chem. Res. Toxicol., 9, 41 (1996)
• Bruning, T., et al.: Toxicol. Sci., 41, 157 (1996)
• Newman, D., et al.: Drug Metab. Disposition, 35, 43 (1996)