(2S)-2-acetamido-3-[(1-hydroxybut-3-en-2-yl)sulfanyl]propanoic acid; (2S)-2-acetamido-3-[(2-hydroxybut-3-en-1-yl)sulfanyl]propanoic acid

• ChemBase ID: 159316
• Molecular Formular: C18H30N2O8S2
• Molecular Mass: 466.5694
• Monoisotopic Mass: 466.14435793
• SMILES: C=CC(CSC[C@@H](NC(=O)C)C(=O)O)O.S(C[C@@H](NC(=O)C)C(=O)O)C(C=C)CO
• Canonical SMILES: OCC(SC[C@H](C(=O)O)NC(=O)C)C=C.C=CC(CSC[C@H](C(=O)O)NC(=O)C)O
• InChI: InChI=1S/2C9H15NO4S/c1-3-7(12)4-15-5-8(9(13)14)10-6(2)11;1-3-7(4-11)15-5-8(9(13)14)10-6(2)12/h3,7-8,12H,1,4-5H2,2H3,(H,10,11)(H,13,14);3,7-8,11H,1,4-5H2,2H3,(H,10,12)(H,13,14)/t2*7?,8-/m11/s1
• InChIKey: IEWINGYEAUEHJQ-CKACUNDDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-acetamido-3-[(1-hydroxybut-3-en-2-yl)sulfanyl]propanoic acid; (2S)-2-acetamido-3-[(2-hydroxybut-3-en-1-yl)sulfanyl]propanoic acid
• IUPAC Traditional name: (2S)-2-acetamido-3-[(1-hydroxybut-3-en-2-yl)sulfanyl]propanoic acid; (2S)-2-acetamido-3-[(2-hydroxybut-3-en-1-yl)sulfanyl]propanoic acid
• Synonyms: MHBMA; (R,S)-N-Acetyl-S-[1-(hydroxymethyl)-2-propen-1-yl)-L-cysteine + (R,S)-N-Acetyl-S-(2-hydroxy-3-buten-1-yl)-L-cysteine (Approximately 1:1 Mixture)

Database IDs

• PubChem SID: 162253451
• PubChem CID: 71312919

CALCULATED PROPERTIES

• Acid pKa: 3.9255295
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.064174
• LogD (pH = 7.4): -3.6832895
• Log P: -0.48307407
• Molar Refractivity: 57.6468 cm^3
• Polarizability: 22.562737 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Thick Yellow Oil

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A179005

A mixture of 2 metabolites of butadiene. The isomeric ratio has been determine to be approximately 1:1 based on proton nmr integration.

REFERENCES

• Barnsley, E.A., et al.: Biochem. J., 100, 362 (1966)