(6S,8aS)-N-({1-[(E)-N'-hydroxycarbamimidoyl]piperidin-4-yl}methyl)-4-oxo-2-phenylmethanesulfonyl-octahydropyrrolo[1,2-a]piperazine-6-carboxamide

• ChemBase ID: 2444
• Molecular Formular: C22H32N6O5S
• Molecular Mass: 492.59168
• Monoisotopic Mass: 492.21548915
• SMILES: N/C(=N\O)/N1CCC(CC1)CNC(=O)[C@@H]1CC[C@H]2CN(CC(=O)N12)S(=O)(=O)Cc1ccccc1
• Canonical SMILES: O/N=C(/N1CCC(CC1)CNC(=O)[C@@H]1CC[C@@H]2N1C(=O)CN(C2)S(=O)(=O)Cc1ccccc1)\N
• InChI: InChI=1S/C22H32N6O5S/c23-22(25-31)26-10-8-16(9-11-26)12-24-21(30)19-7-6-18-13-27(14-20(29)28(18)19)34(32,33)15-17-4-2-1-3-5-17/h1-5,16,18-19,31H,6-15H2,(H2,23,25)(H,24,30)/t18-,19-/m0/s1
• InChIKey: DHTSUHWLPAEEQB-OALUTQOASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S,8aS)-N-({1-[(E)-N'-hydroxycarbamimidoyl]piperidin-4-yl}methyl)-4-oxo-2-phenylmethanesulfonyl-octahydropyrrolo[1,2-a]piperazine-6-carboxamide
• IUPAC Traditional name: (6S,8aS)-N-({1-[(E)-N'-hydroxycarbamimidoyl]piperidin-4-yl}methyl)-4-oxo-2-phenylmethanesulfonyl-hexahydropyrrolo[1,2-a]piperazine-6-carboxamide
• Synonyms: 4-Oxo-2-Phenylmethanesulfonyl-Octahydro-Pyrrolo[1,2-a]Pyrazine-6-Carboxylic Acid [1-(N-Hydroxycarbamimidoyl)-Piperidin-4-Ylmethyl]-Amide

Database IDs

• PubChem SID: 46504445; 160965895
• PubChem CID: 5326608

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.146958
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.7966642
• LogD (pH = 7.4): -1.3417366
• Log P: -1.0953275
• Molar Refractivity: 125.6467 cm^3
• Polarizability: 49.142803 Å^3
• Polar Surface Area: 148.64 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.02
• LOG S: -2.67
• Solubility (Water): 1.06e+00 g/l

DETAILS

DrugBank - DB02723

Drug information: experimental