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

• ChemBase ID: 159301
• Molecular Formular: C9H15NO4S
• Molecular Mass: 233.2847
• Monoisotopic Mass: 233.07217897
• SMILES: OC/C=C/CSC[C@@H](NC(=O)C)C(=O)O
• Canonical SMILES: OC/C=C/CSC[C@H](C(=O)O)NC(=O)C
• InChI: InChI=1S/C9H15NO4S/c1-7(12)10-8(9(13)14)6-15-5-3-2-4-11/h2-3,8,11H,4-6H2,1H3,(H,10,12)(H,13,14)/b3-2+/t8-/m1/s1
• InChIKey: CGYFKBWVTSXRDZ-UFUPEUMYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162253436
• PubChem CID: 71312910

CALCULATED PROPERTIES

• Acid pKa: 3.924493
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.1730661
• LogD (pH = 7.4): -3.7917337
• Log P: -0.59096783
• Molar Refractivity: 58.9785 cm^3
• Polarizability: 22.56307 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Light Yellow Solid
• Melting Point: 115-120°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A178650

A novel 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)