(2R)-N-(1-cyanocyclopropyl)-3-{[(2S)-5-oxopyrrolidin-2-yl]methanesulfonyl}-2-{[(1S)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl]amino}propanamide

• ChemBase ID: 5229
• Molecular Formular: C20H22F4N4O4S
• Molecular Mass: 490.4716928
• Monoisotopic Mass: 490.12978908
• SMILES: c1(ccc(cc1)[C@H](N[C@H](C(=O)NC1(CC1)C#N)CS(=O)(=O)C[C@@H]1CCC(=O)N1)C(F)(F)F)F
• Canonical SMILES: N#CC1(CC1)NC(=O)[C@H](CS(=O)(=O)C[C@@H]1CCC(=O)N1)N[C@H](C(F)(F)F)c1ccc(cc1)F
• InChI: InChI=1S/C20H22F4N4O4S/c21-13-3-1-12(2-4-13)17(20(22,23)24)27-15(18(30)28-19(11-25)7-8-19)10-33(31,32)9-14-5-6-16(29)26-14/h1-4,14-15,17,27H,5-10H2,(H,26,29)(H,28,30)/t14-,15-,17-/m0/s1
• InChIKey: JLPXDVXMMYRTKN-ZOBUZTSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-N-(1-cyanocyclopropyl)-3-{[(2S)-5-oxopyrrolidin-2-yl]methanesulfonyl}-2-{[(1S)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl]amino}propanamide
• IUPAC Traditional name: (2R)-N-(1-cyanocyclopropyl)-3-{[(2S)-5-oxopyrrolidin-2-yl]methanesulfonyl}-2-{[(1S)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl]amino}propanamide
• Synonyms: N-(1-CYANOCYCLOPROPYL)-3-({[(2S)-5-OXOPYRROLIDIN-2-YL]METHYL}SULFONYL)-N~2~-[(1S)-2,2,2-TRIFLUORO-1-(4-FLUOROPHENYL)ETHYL]-L-ALANINAMIDE

Database IDs

• PubChem SID: 160968658; 99444058
• PubChem CID: 11840933

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.1100698
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.08245252
• LogD (pH = 7.4): -0.6374089
• Log P: 0.16599138
• Molar Refractivity: 107.0363 cm^3
• Polarizability: 41.90891 Å^3
• Polar Surface Area: 128.16 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.49
• LOG S: -3.37
• Solubility (Water): 2.10e-01 g/l

DETAILS

DrugBank - DB07587

Drug information: experimental