benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(2S)-1-oxopentan-2-yl]carbamoyl}butyl]carbamoyl}butyl]carbamate

• ChemBase ID: 133928
• Molecular Formular: C25H39N3O5
• Molecular Mass: 461.59426
• Monoisotopic Mass: 461.28897136
• SMILES: CCC[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1
• Canonical SMILES: CCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C)CC(C)C)C=O
• InChI: InChI=1S/C25H39N3O5/c1-6-10-20(15-29)26-23(30)21(13-17(2)3)27-24(31)22(14-18(4)5)28-25(32)33-16-19-11-8-7-9-12-19/h7-9,11-12,15,17-18,20-22H,6,10,13-14,16H2,1-5H3,(H,26,30)(H,27,31)(H,28,32)/t20-,21-,22-/m0/s1
• InChIKey: QEJRGURBLQWEOU-FKBYEOEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(2S)-1-oxopentan-2-yl]carbamoyl}butyl]carbamoyl}butyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(2S)-1-oxopentan-2-yl]carbamoyl}butyl]carbamoyl}butyl]carbamate
• Synonyms: MG115; Z-LLnV; Z-Leu-Leu-Norvalinal

Database IDs

• CAS Number: 133407-86-0
• PubChem SID: 162228205
• PubChem CID: 9868928

CALCULATED PROPERTIES

• Acid pKa: 12.445417
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.8275566
• LogD (pH = 7.4): 3.8275533
• Log P: 3.8275566
• Molar Refractivity: 126.3189 cm^3
• Polarizability: 49.722332 Å^3
• Polar Surface Area: 113.6 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: 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 ... PSMA1(5682), PSMC1(5700)mouse ... PSMA1(26440), PSMC1(19179)rat ... PSMA1(29668), PSMC1(117263)

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - C6706

Amino Acid Sequence
Z-Leu-Leu-Nva
Biochem/physiol Actions
Potent inhibitor of the 20S proteasome (Ki = 21 nM) and 26S proteasome (Ki = 35 nM). Cells treated with 54 μM N-CBZ-Leu-Leu-Norvalinal showed complete block of the G1/S and metaphase transitions and delayed passage through S-phase. Induces apoptosis in Rat-1 and PC12 cells, perhaps by accumulation of stabilized p53.