5-chloro-N-[(3S,4S)-1-({[2-fluoro-4-(2-oxo-1,2-dihydropyridin-1-yl)phenyl]carbamoyl}methyl)-4-hydroxypyrrolidin-3-yl]thiophene-2-carboxamide

• ChemBase ID: 5508
• Molecular Formular: C22H20ClFN4O4S
• Molecular Mass: 490.9350032
• Monoisotopic Mass: 490.08778204
• SMILES: Fc1cc(n2ccccc2=O)ccc1NC(=O)CN1C[C@H](O)[C@H](C1)NC(=O)c1ccc(s1)Cl
• Canonical SMILES: O=C(Nc1ccc(cc1F)n1ccccc1=O)CN1C[C@@H]([C@H](C1)O)NC(=O)c1ccc(s1)Cl
• InChI: InChI=1S/C22H20ClFN4O4S/c23-19-7-6-18(33-19)22(32)26-16-10-27(11-17(16)29)12-20(30)25-15-5-4-13(9-14(15)24)28-8-2-1-3-21(28)31/h1-9,16-17,29H,10-12H2,(H,25,30)(H,26,32)/t16-,17-/m0/s1
• InChIKey: ARAVOODWJJJNBY-IRXDYDNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-N-[(3S,4S)-1-({[2-fluoro-4-(2-oxo-1,2-dihydropyridin-1-yl)phenyl]carbamoyl}methyl)-4-hydroxypyrrolidin-3-yl]thiophene-2-carboxamide
• IUPAC Traditional name: 5-chloro-N-[(3S,4S)-1-({[2-fluoro-4-(2-oxopyridin-1-yl)phenyl]carbamoyl}methyl)-4-hydroxypyrrolidin-3-yl]thiophene-2-carboxamide
• Synonyms: 5-Chloro-thiophene-2-carboxylic acid ((3S,4S)-1-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-methyl}-4-hydroxy-pyrrolidin-3-yl)-amide

Database IDs

• PubChem SID: 99444346; 160968936
• PubChem CID: 11979006

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.566074
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.9108791
• LogD (pH = 7.4): 1.9861945
• Log P: 1.9872737
• Molar Refractivity: 123.8104 cm^3
• Polarizability: 46.05952 Å^3
• Polar Surface Area: 101.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.44
• LOG S: -5.2
• Solubility (Water): 3.12e-03 g/l

DETAILS

DrugBank - DB07875

Drug information: experimental