(2S,4S)-1-acetyl-N-[(2R)-1-(1,3-benzothiazol-2-yl)-5-carbamimidamido-1-oxopentan-2-yl]-4-hydroxypyrrolidine-2-carboxamide

• ChemBase ID: 2525
• Molecular Formular: C20H26N6O4S
• Molecular Mass: 446.52324
• Monoisotopic Mass: 446.17362434
• SMILES: CC(=O)N1C[C@@H](O)C[C@H]1C(=O)N[C@H](CCCNC(=N)N)C(=O)c1nc2c(s1)cccc2
• Canonical SMILES: NC(=N)NCCC[C@H](C(=O)c1nc2c(s1)cccc2)NC(=O)[C@@H]1C[C@@H](CN1C(=O)C)O
• InChI: InChI=1S/C20H26N6O4S/c1-11(27)26-10-12(28)9-15(26)18(30)24-14(6-4-8-23-20(21)22)17(29)19-25-13-5-2-3-7-16(13)31-19/h2-3,5,7,12,14-15,28H,4,6,8-10H2,1H3,(H,24,30)(H4,21,22,23)/t12-,14+,15-/m0/s1
• InChIKey: VXDAVYUFYPFGDX-CFVMTHIKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-1-acetyl-N-[(2R)-1-(1,3-benzothiazol-2-yl)-5-carbamimidamido-1-oxopentan-2-yl]-4-hydroxypyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S,4S)-1-acetyl-N-[(2R)-1-(1,3-benzothiazol-2-yl)-5-carbamimidamido-1-oxopentan-2-yl]-4-hydroxypyrrolidine-2-carboxamide
• Synonyms: (2s,4r)-1-Acetyl-N-[(1s)-4-[(Aminoiminomethyl)Amino]-1-(2-Benzothiazolylcarbonyl)Butyl]-4-Hydroxy-2-Pyrrolidinecarboxamide

Database IDs

• PubChem SID: 160965975; 46509114
• PubChem CID: 46936500

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.370926
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -3.225046
• LogD (pH = 7.4): -3.2203474
• Log P: -1.1290715
• Molar Refractivity: 124.0363 cm^3
• Polarizability: 45.02014 Å^3
• Polar Surface Area: 161.5 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.1
• LOG S: -3.52
• Solubility (Water): 1.34e-01 g/l

DETAILS

DrugBank - DB02812

Drug information: experimental