(2R)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoic acid

• ChemBase ID: 128003
• Molecular Formular: C15H24N2O7S
• Molecular Mass: 376.42526
• Monoisotopic Mass: 376.13042212
• SMILES: O=C1NC(C(=O)SC[C@@H](C(=O)O)NC(=O)C)([C@@H](O)[C@H]1C)[C@@H](O)C(C)C
• Canonical SMILES: CC(=O)N[C@H](C(=O)O)CSC(=O)C1(NC(=O)[C@@H]([C@@H]1O)C)[C@H](C(C)C)O
• InChI: InChI=1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10+,11+,15?/m1/s1
• InChIKey: DAQAKHDKYAWHCG-WVDSPMRNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoic acid
• IUPAC Traditional name: (2R)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoic acid
• Synonyms: Lactacystin

Database IDs

• CAS Number: 133343-34-7
• PubChem SID: 162222319
• PubChem CID: 3870; 3034764
• CHEBI ID: 52722
• CHEMBL: 374308
• Chemspider ID: 3735
• MeSH Name: Lactacystin
• Wikipedia Title: Lactacystin

CALCULATED PROPERTIES

• Acid pKa: 3.6403015
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.0795863
• LogD (pH = 7.4): -4.552016
• Log P: -1.2231128
• Molar Refractivity: 88.0327 cm^3
• Polarizability: 35.217537 Å^3
• Polar Surface Area: 153.03 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Partition Coefficient: 0.086
• pKa: 3.106
• pKb: 10.891