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

• ChemBase ID: 5201
• Molecular Formular: C20H37N3O4
• Molecular Mass: 383.52548
• Monoisotopic Mass: 383.27840668
• SMILES: N([C@H](C(=O)N[C@H](C(=O)N[C@H](C=O)CCCC)CC(C)C)CC(C)C)C(=O)C
• Canonical SMILES: CCCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(C)C)CC(C)C)C=O
• InChI: InChI=1S/C20H37N3O4/c1-7-8-9-16(12-24)22-19(26)18(11-14(4)5)23-20(27)17(10-13(2)3)21-15(6)25/h12-14,16-18H,7-11H2,1-6H3,(H,21,25)(H,22,26)(H,23,27)/t16-,17-,18-/m0/s1
• InChIKey: FMYKJLXRRQTBOR-BZSNNMDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-acetamido-4-methylpentanamido]-4-methyl-N-[(2S)-1-oxohexan-2-yl]pentanamide
• IUPAC Traditional name: N-ac-leu-leu-norleucinal; (2S)-2-[(2S)-2-acetamido-4-methylpentanamido]-4-methyl-N-[(2S)-1-oxohexan-2-yl]pentanamide
• Synonyms: 2-ACETYLAMINO-4-METHYL-PENTANOIC ACID [1-(1-FORMYL-PENTYLCARBAMOYL)-3-METHYL-BUTYL]-AMIDE; ALLN; Ac-LLnL-CHO; MG-101; N-Acetyl-Leu-Leu-Norleu-al; N-Acetyl-L-leucyl-L-leucyl-L-norleucinal; Calpain Inhibitor I

Database IDs

• CAS Number: 110044-82-1
• MDL Number: MFCD00065505
• Beilstein Number: 7656053
• PubChem SID: 24852739; 160968631; 24891066; 99444029
• PubChem CID: 443118

CALCULATED PROPERTIES

JChem

• LogD (pH = 7.4): 1.928358
• Log P: 1.928361
• Molar Refractivity: 104.6837 cm^3
• Polarizability: 41.28852 Å^3
• Polar Surface Area: 104.37 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true
• Acid pKa: 12.485252
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.9283609

ALOGPS 2.1

• Log P: 2.22
• LOG S: -3.81
• Solubility (Water): 5.96e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble
• 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

Pharmacology Properties

• Gene Information: human ... CAPN1(823), CTSB(1508), PSMA1(5682)

Product Information

• Purity: ≥97% (TLC); ≥97.0% (TLC)
• Empirical Formula (Hill Notation): C20H37N3O4

DETAILS

DrugBank - DB07558

Drug information: experimental

Sigma Aldrich - A6185

Application
Calpain inhibitor I reversibly blocks the calcium-dependent neutral cysteine protease calpain I. Calpains have been implicated in various cellular processes, including cell proliferation, apoptosis, and cell differentiation.
Biochem/physiol Actions
Can initiate apoptosis in HL-60 cells1 but blocks dexamethasone-induced apoptosis in thymocytes and cycloheximide-induced apoptosis in metamyelocytes.2 Inhibits cyclin B degradation and arrests the cell cycle at G1/S and at meta-/anaphase.3 Blocks induction of nitric oxide synthase by LPS in macrophages.4

Sigma Aldrich - 21277

Other Notes
Shows marked inhibition of cathepsin L1