(2S)-1-[(2S,3S)-2-{[(2S,3S)-3-(benzylcarbamoyl)oxiran-2-yl]formamido}-3-methylpentanoyl]pyrrolidine-2-carboxylic acid

• ChemBase ID: 4882
• Molecular Formular: C22H29N3O6
• Molecular Mass: 431.48216
• Monoisotopic Mass: 431.20563566
• SMILES: N(Cc1ccccc1)C(=O)[C@H]1O[C@@H]1C(=O)N[C@H](C(=O)N1[C@H](C(=O)O)CCC1)[C@H](CC)C
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N1CCC[C@H]1C(=O)O)NC(=O)[C@H]1O[C@@H]1C(=O)NCc1ccccc1)C
• InChI: InChI=1S/C22H29N3O6/c1-3-13(2)16(21(28)25-11-7-10-15(25)22(29)30)24-20(27)18-17(31-18)19(26)23-12-14-8-5-4-6-9-14/h4-6,8-9,13,15-18H,3,7,10-12H2,1-2H3,(H,23,26)(H,24,27)(H,29,30)/t13-,15-,16-,17-,18-/m0/s1
• InChIKey: MERYMLLGRCNRKE-HILJTLORSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S,3S)-2-{[(2S,3S)-3-(benzylcarbamoyl)oxiran-2-yl]formamido}-3-methylpentanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S)-1-[(2S,3S)-2-{[(2S,3S)-3-(benzylcarbamoyl)oxiran-2-yl]formamido}-3-methylpentanoyl]pyrrolidine-2-carboxylic acid
• Synonyms: N-({(2S,3S)-3-[(BENZYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINE

Database IDs

• PubChem SID: 99443702; 160968314
• PubChem CID: 23647361

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.8102834
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.68646234
• LogD (pH = 7.4): -2.251835
• Log P: 1.0058017
• Molar Refractivity: 109.9153 cm^3
• Polarizability: 43.261616 Å^3
• Polar Surface Area: 128.34 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.31
• LOG S: -2.95
• Solubility (Water): 4.84e-01 g/l

DETAILS

DrugBank - DB07231

Drug information: experimental