methyl (2S)-2-acetamido-3-{[(2E)-4-hydroxybut-2-en-1-yl]sulfanyl}propanoate

• ChemBase ID: 159303
• Molecular Formular: C10H17NO4S
• Molecular Mass: 247.31128
• Monoisotopic Mass: 247.08782903
• SMILES: OC/C=C/CSC[C@H](C(=O)OC)NC(=O)C
• Canonical SMILES: OC/C=C/CSC[C@H](C(=O)OC)NC(=O)C
• InChI: InChI=1S/C10H17NO4S/c1-8(13)11-9(10(14)15-2)7-16-6-4-3-5-12/h3-4,9,12H,5-7H2,1-2H3,(H,11,13)/b4-3+/t9-/m1/s1
• InChIKey: CPBMMSFMHHNWEC-CDAZIORVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-acetamido-3-{[(2E)-4-hydroxybut-2-en-1-yl]sulfanyl}propanoate
• IUPAC Traditional name: methyl (2S)-2-acetamido-3-{[(2E)-4-hydroxybut-2-en-1-yl]sulfanyl}propanoate
• Synonyms: N-Acetyl-S-(4-hydroxy-2-butenyl)-L-cysteine Methyl Ester; N-Acetyl-S-(4-hydroxy-2-buten-1-yl)-L-cysteine Methyl Ester

Database IDs

• PubChem SID: 162253438
• PubChem CID: 71312912

CALCULATED PROPERTIES

• Acid pKa: 12.369283
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.44507387
• LogD (pH = 7.4): -0.4450779
• Log P: -0.44507378
• Molar Refractivity: 63.7476 cm^3
• Polarizability: 24.629557 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Pale Yellow Oil

DETAILS

Toronto Research Chemicals - A178660

A protected metabolite of Butadiene monoepoxide (BMO), a mutagen and carcinogen compound.

REFERENCES

• Cheng, X., et al.: Drug Metab. Dispos., 21, 121 (1993)
• Nieusma, J., et al.: Chem. Res. Toxicol., 10, 450 (1993)