(2S,3S)-2-amino-4-cyclopropyl-3-[(3R,5R)-3-(2-fluoro-4-methanesulfonylphenyl)-1,2,4-oxadiazolidin-5-yl]-1-[(3S)-3-fluoropyrrolidin-1-yl]butan-1-one

• ChemBase ID: 4646
• Molecular Formular: C20H28F2N4O4S
• Molecular Mass: 458.5225264
• Monoisotopic Mass: 458.17993284
• SMILES: [C@@H]([C@@H](C(=O)N1C[C@H](CC1)F)N)(CC1CC1)[C@@H]1N[C@H](NO1)c1ccc(cc1F)S(=O)(=O)C
• Canonical SMILES: F[C@H]1CCN(C1)C(=O)[C@H]([C@@H]([C@H]1ON[C@@H](N1)c1ccc(cc1F)S(=O)(=O)C)CC1CC1)N
• InChI: InChI=1S/C20H28F2N4O4S/c1-31(28,29)13-4-5-14(16(22)9-13)18-24-19(30-25-18)15(8-11-2-3-11)17(23)20(27)26-7-6-12(21)10-26/h4-5,9,11-12,15,17-19,24-25H,2-3,6-8,10,23H2,1H3/t12-,15-,17-,18+,19+/m0/s1
• InChIKey: PTAHVQJZNFGPHN-MQPLHJKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-amino-4-cyclopropyl-3-[(3R,5R)-3-(2-fluoro-4-methanesulfonylphenyl)-1,2,4-oxadiazolidin-5-yl]-1-[(3S)-3-fluoropyrrolidin-1-yl]butan-1-one
• IUPAC Traditional name: (2S,3S)-2-amino-4-cyclopropyl-3-[(3R,5R)-3-(2-fluoro-4-methanesulfonylphenyl)-1,2,4-oxadiazolidin-5-yl]-1-[(3S)-3-fluoropyrrolidin-1-yl]butan-1-one
• Synonyms: (2S,3S)-4-cyclopropyl-3-{(3R,5R)-3-[2-fluoro-4-(methylsulfonyl)phenyl]-1,2,4-oxadiazolidin-5-yl}-1-[(3S)-3-fluoropyrrolidin-1-yl]-1-oxobutan-2-amine

Database IDs

• PubChem SID: 160968078; 99443464
• PubChem CID: 46937042

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.66944
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.9206723
• LogD (pH = 7.4): -0.2872896
• Log P: 0.72389424
• Molar Refractivity: 119.3072 cm^3
• Polarizability: 44.04945 Å^3
• Polar Surface Area: 113.76 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.38
• LOG S: -2.85
• Solubility (Water): 6.55e-01 g/l

DETAILS

DrugBank - DB06993

Drug information: experimental