(2S)-1-[(2S)-3-methyl-2-{[(2S,3S)-3-(propylcarbamoyl)oxiran-2-yl]formamido}pentanoyl]pyrrolidine-2-carboxylic acid

• ChemBase ID: 155702
• Molecular Formular: C18H29N3O6
• Molecular Mass: 383.43936
• Monoisotopic Mass: 383.20563566
• SMILES: CCCNC(=O)[C@@H]1[C@H](O1)C(=O)N[C@@H](C(C)CC)C(=O)N1CCC[C@H]1C(=O)O
• Canonical SMILES: CCCNC(=O)[C@H]1O[C@@H]1C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)O)C(CC)C
• InChI: InChI=1S/C18H29N3O6/c1-4-8-19-15(22)13-14(27-13)16(23)20-12(10(3)5-2)17(24)21-9-6-7-11(21)18(25)26/h10-14H,4-9H2,1-3H3,(H,19,22)(H,20,23)(H,25,26)/t10?,11-,12-,13-,14-/m0/s1
• InChIKey: ZEZGJKSEBRELAS-NSIINPIOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-3-methyl-2-{[(2S,3S)-3-(propylcarbamoyl)oxiran-2-yl]formamido}pentanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S)-1-[(2S)-3-methyl-2-{[(2S,3S)-3-(propylcarbamoyl)oxiran-2-yl]formamido}pentanoyl]pyrrolidine-2-carboxylic acid
• Synonyms: (L-3-trans-(Propylcarbamyl)oxirane-2-carbonyl)-L-isoleucyl-L-proline; CA-074

Database IDs

• CAS Number: 134448-10-5
• MDL Number: MFCD00797531
• PubChem SID: 162249840; 24892580
• PubChem CID: 16219107

CALCULATED PROPERTIES

• Acid pKa: 3.8102834
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.5316051
• LogD (pH = 7.4): -3.0969768
• Log P: 0.16065896
• Molar Refractivity: 94.5753 cm^3
• Polarizability: 37.418144 Å^3
• Polar Surface Area: 128.34 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99% (TLC)
• Empirical Formula (Hill Notation): C18H29N3O6

DETAILS

Sigma Aldrich - C5732

Application
Inhibitor of Cathepsin B.