(2R)-2-acetamido-3-[(4-nitrophenyl)sulfanyl]propanoic acid

• ChemBase ID: 175363
• Molecular Formular: C11H12N2O5S
• Molecular Mass: 284.28838
• Monoisotopic Mass: 284.04669249
• SMILES: c1c(ccc(c1)SC[C@H](NC(=O)C)C(=O)O)[N+](=O)[O-]
• Canonical SMILES: CC(=O)N[C@H](C(=O)O)CSc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C11H12N2O5S/c1-7(14)12-10(11(15)16)6-19-9-4-2-8(3-5-9)13(17)18/h2-5,10H,6H2,1H3,(H,12,14)(H,15,16)/t10-/m0/s1
• InChIKey: LOBKSYPZBSVLLE-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-acetamido-3-[(4-nitrophenyl)sulfanyl]propanoic acid
• IUPAC Traditional name: (2R)-2-acetamido-3-[(4-nitrophenyl)sulfanyl]propanoic acid
• Synonyms: N-Acetyl-S-(4-nitrophenyl)-L-cysteine; N-Acetyl-3-[(p-nitrophenyl)thio]alanine; S-(4-Nitrophenyl)mercapturic Acid

Database IDs

• CAS Number: 91088-55-0
• PubChem SID: 164231273
• PubChem CID: 185069

CALCULATED PROPERTIES

• Acid pKa: 2.9032223
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.5563694
• LogD (pH = 7.4): -2.491452
• Log P: 0.9935641
• Molar Refractivity: 69.5683 cm^3
• Polarizability: 26.313896 Å^3
• Polar Surface Area: 112.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Yellow to Pale Brown Solid
• Melting Point: 150-152°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N504410

Used as a marker for low levels of exposure to benzene in industry.

REFERENCES

• van Sittert, N.J., et al.: Br. J. Med., 50, 460 (1993)
• Boogaard, P.J. and van Sittert, H.J.: Occup. Environ. Med., 52, 611 (1995)