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

• ChemBase ID: 159320
• Molecular Formular: C20H34N2O8S2
• Molecular Mass: 494.62256
• Monoisotopic Mass: 494.17565806
• SMILES: C=C(C(CSC[C@@H](NC(=O)C)C(=O)O)O)C.C=C(C(SC[C@@H](NC(=O)C)C(=O)O)CO)C
• Canonical SMILES: CC(=O)N[C@@H](C(=O)O)CSCC(C(=C)C)O.OCC(C(=C)C)SC[C@H](C(=O)O)NC(=O)C
• InChI: InChI=1S/2C10H17NO4S/c1-6(2)9(4-12)16-5-8(10(14)15)11-7(3)13;1-6(2)9(13)5-16-4-8(10(14)15)11-7(3)12/h8-9,12H,1,4-5H2,2-3H3,(H,11,13)(H,14,15);8-9,13H,1,4-5H2,2-3H3,(H,11,12)(H,14,15)/t2*8-,9?/m11/s1
• InChIKey: QSPVFMIJNHLPRN-IESZQLCYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162253455
• PubChem CID: 71312927

CALCULATED PROPERTIES

• Acid pKa: 3.99675
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.7523167
• LogD (pH = 7.4): -3.4006448
• Log P: -0.2397128
• Molar Refractivity: 61.9288 cm^3
• Polarizability: 24.387918 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A179020

A mixture of 2 possible metabolites of isoprene.