(2R,3S)-N-[(1S)-1-{[(4-carbamimidoylphenyl)methyl]carbamoyl}-3-(methylsulfanyl)propyl]-3-hydroxy-2-(propane-1-sulfonamido)butanamide

• ChemBase ID: 4313
• Molecular Formular: C20H33N5O5S2
• Molecular Mass: 487.63652
• Monoisotopic Mass: 487.19231118
• SMILES: N=C(N)c1ccc(CNC(=O)[C@H](CCSC)NC(=O)[C@H](NS(=O)(=O)CCC)[C@H](C)O)cc1
• Canonical SMILES: CSCC[C@@H](C(=O)NCc1ccc(cc1)C(=N)N)NC(=O)[C@@H]([C@@H](O)C)NS(=O)(=O)CCC
• InChI: InChI=1S/C20H33N5O5S2/c1-4-11-32(29,30)25-17(13(2)26)20(28)24-16(9-10-31-3)19(27)23-12-14-5-7-15(8-6-14)18(21)22/h5-8,13,16-17,25-26H,4,9-12H2,1-3H3,(H3,21,22)(H,23,27)(H,24,28)/t13-,16-,17+/m0/s1
• InChIKey: AIIJKVORRBMJHS-RRQGHBQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-N-[(1S)-1-{[(4-carbamimidoylphenyl)methyl]carbamoyl}-3-(methylsulfanyl)propyl]-3-hydroxy-2-(propane-1-sulfonamido)butanamide
• IUPAC Traditional name: (2R,3S)-N-[(1S)-1-{[(4-carbamimidoylphenyl)methyl]carbamoyl}-3-(methylsulfanyl)propyl]-3-hydroxy-2-(propane-1-sulfonamido)butanamide
• Synonyms: N-[1-(4-CARBAMIMIDOYL-BENZYLCARBAMOYL)-3-METHYLSULFANYL-PROPYL]-3-HYDROXY-2-PROPOXYAMINO-BUTYRAMID

Database IDs

• PubChem SID: 160967745; 46505133
• PubChem CID: 5289214

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.588605
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -3.0547419
• LogD (pH = 7.4): -2.1165552
• Log P: -0.97545516
• Molar Refractivity: 136.2911 cm^3
• Polarizability: 49.45112 Å^3
• Polar Surface Area: 174.47 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.1
• LOG S: -3.92
• Solubility (Water): 5.89e-02 g/l

DETAILS

DrugBank - DB04767

Drug information: experimental