benzyl N-[(1S)-2-methyl-1-[(1-oxo-3-phenylpropan-2-yl)carbamoyl]propyl]carbamate

• ChemBase ID: 153732
• Molecular Formular: C22H26N2O4
• Molecular Mass: 382.45284
• Monoisotopic Mass: 382.18925732
• SMILES: CC(C)[C@@H](C(=O)NC(Cc1ccccc1)C=O)NC(=O)OCc1ccccc1
• Canonical SMILES: O=CC(NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1)Cc1ccccc1
• InChI: InChI=1S/C22H26N2O4/c1-16(2)20(24-22(27)28-15-18-11-7-4-8-12-18)21(26)23-19(14-25)13-17-9-5-3-6-10-17/h3-12,14,16,19-20H,13,15H2,1-2H3,(H,23,26)(H,24,27)/t19?,20-/m0/s1
• InChIKey: NGBKFLTYGSREKK-ANYOKISRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-2-methyl-1-[(1-oxo-3-phenylpropan-2-yl)carbamoyl]propyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-2-methyl-1-[(1-oxo-3-phenylpropan-2-yl)carbamoyl]propyl]carbamate
• Synonyms: Calpain Inhibitor III; MDL 28170

Database IDs

• CAS Number: 88191-84-8
• MDL Number: MFCD00798796
• PubChem SID: 24278565; 162247871
• PubChem CID: 11199915

CALCULATED PROPERTIES

• Acid pKa: 12.718617
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.432586
• LogD (pH = 7.4): 3.432584
• Log P: 3.432586
• Molar Refractivity: 106.1639 cm^3
• Polarizability: 41.516533 Å^3
• Polar Surface Area: 84.5 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble26 mg/mL; H2O: insoluble; methanol: soluble

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CAPN1(823), CAPN2(824)

Product Information

• Purity: ≥95% (HPLC)
• Compostion: Peptide Content, >90%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C22H26N2O4

DETAILS

Sigma Aldrich - M6690

Amino Acid Sequence
Z-Val-Phe-al
Biochem/physiol Actions
MDL 28170 is a potent cell permeable calpain I and II inhibitor; reduces capsaicin-mediated cell death in cultured dorsal root ganglion neurons. Reduced occurrence of apoptosis in H2O2 and A23187 treated PC12 cells. γ-secretase-inhibitor.