(2S)-2-[(2S)-2-acetamido-4-methylpentanamido]-4-methyl-N-[(2S)-4-(methylsulfanyl)-1-oxobutan-2-yl]pentanamide

• ChemBase ID: 155176
• Molecular Formular: C19H35N3O4S
• Molecular Mass: 401.5639
• Monoisotopic Mass: 401.23482762
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C=O)NC(=O)C
• Canonical SMILES: CSCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(C)C)CC(C)C)C=O
• InChI: InChI=1S/C19H35N3O4S/c1-12(2)9-16(20-14(5)24)19(26)22-17(10-13(3)4)18(25)21-15(11-23)7-8-27-6/h11-13,15-17H,7-10H2,1-6H3,(H,20,24)(H,21,25)(H,22,26)/t15-,16-,17-/m0/s1
• InChIKey: RJWLAIMXRBDUMH-ULQDDVLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-acetamido-4-methylpentanamido]-4-methyl-N-[(2S)-4-(methylsulfanyl)-1-oxobutan-2-yl]pentanamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-acetamido-4-methylpentanamido]-4-methyl-N-[(2S)-4-(methylsulfanyl)-1-oxobutan-2-yl]pentanamide
• Synonyms: N-Acetyl-L-leucyl-L-leucyl-L-methioninal; Calpain Inhibitor II

Database IDs

• CAS Number: 136632-32-1
• MDL Number: MFCD00065506
• Beilstein Number: 7693643
• PubChem SID: 24891051; 162249314
• PubChem CID: 121855

CALCULATED PROPERTIES

• Acid pKa: 12.425297
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.1681296
• LogD (pH = 7.4): 1.1681261
• Log P: 1.1681297
• Molar Refractivity: 108.0464 cm^3
• Polarizability: 42.517815 Å^3
• Polar Surface Area: 104.37 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble20 mg/mL
• Apperance: white powder

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: ≥95% (HPLC); ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C19H35N3O4S

DETAILS

Sigma Aldrich - A6060

Application
Calpain inhibitor II is a cell-permeable peptide that restricts the activity of calpain, cathepsin L and cathepsin B. Calpain inhibitor II also prevents the methylmercury-induced cell death of cultured rat cerebellar neurons.

Sigma Aldrich - 21278

Other Notes
Shows marked inhibition of cathepsin B1