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133407-82-6 molecular structure
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benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(2S)-4-methyl-1-oxopentan-2-yl]carbamoyl}butyl]carbamoyl}butyl]carbamate

ChemBase ID: 73098
Molecular Formular: C26H41N3O5
Molecular Mass: 475.62084
Monoisotopic Mass: 475.30462143
SMILES and InChIs

SMILES:
c1ccc(cc1)COC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C=O)CC(C)C)CC(C)C
Canonical SMILES:
O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C)CC(C)C)CC(C)C
InChI:
InChI=1S/C26H41N3O5/c1-17(2)12-21(15-30)27-24(31)22(13-18(3)4)28-25(32)23(14-19(5)6)29-26(33)34-16-20-10-8-7-9-11-20/h7-11,15,17-19,21-23H,12-14,16H2,1-6H3,(H,27,31)(H,28,32)(H,29,33)/t21-,22-,23-/m0/s1
InChIKey:
TZYWCYJVHRLUCT-VABKMULXSA-N

Cite this record

CBID:73098 http://www.chembase.cn/molecule-73098.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(2S)-4-methyl-1-oxopentan-2-yl]carbamoyl}butyl]carbamoyl}butyl]carbamate
IUPAC Traditional name
benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(2S)-4-methyl-1-oxopentan-2-yl]carbamoyl}butyl]carbamoyl}butyl]carbamate
Synonyms
MG-132
MG132
MG132
Z-Leu-Leu-Leu-al
CAS Number
133407-82-6
MDL Number
MFCD00674886
PubChem SID
162038018
24892475
PubChem CID
462382

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 462382 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.466964  H Acceptors
H Donor LogD (pH = 5.5) 4.114576 
LogD (pH = 7.4) 4.1145725  Log P 4.114576 
Molar Refractivity 130.8675 cm3 Polarizability 51.56013 Å3
Polar Surface Area 113.6 Å2 Rotatable Bonds 15 
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO: soluble expand Show data source
Apperance
powder expand Show data source
Storage Condition
-20°C expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Target
Proteasome expand Show data source
Gene Information
human ... CTSB(1508), NFKB1(4790), PSMA1(5682) expand Show data source
Purity
≥90% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Quality
proteasome inhibition tested expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
Selleck Chemicals - S2619 external link
Research Area
Description Cancer
Protocol
Kinase Assay [1]
Measurement of inhibitory activities of MG-132 against 20S proteasome The reaction mixture for the 20S proteasome inhibitory assay contains 0.1 M Tris-acetate, pH 7.0, 20S proteasome, MG-132, and 25 μM substrate dissolved in dimethyl sulfoxide in a final volume of 1 mL. After incuba tion at 37 °C for 15 minutes, the reaction is stopped by the addition of 0.1 mL of 10% SDS and 0.9 mL of 0.1M Tris acetate, pH 9.0. The fluorescence of the reaction products is measured. To determine the IC50 against 20S proteasome, various concentrations of MG-132 are included in the assay mixture.
Cell Assay [5]
Cell Lines KIM-2, HC11, and ES
Concentrations Dissolved in DMSO, final concentrations ~25 μM
Incubation Time 24, and 48 hours
Methods Cells are exposed to various concentrations of MG-132 for 24, and 48 hours. Supernatant and monolayer cells are harvested by centrifugation and fixed in 70% ethanol in PBS for staining with acridine orange. Equal volumes of cells and acridine orange (5 mg/mL in PBS) are mixed on a microscope slide and examined by fluorescence microscopy. For annexin V analysis, cells are harvested by centrifugation and stained with annexin V and propidium iodide. For cell cycle analysis, cells are rehydrated in PBS at room temperature for 10 minutes, followed by staining with propidium iodide (5 mg/mL). All samples are analyzed using a Coulter Epics XL flow cytometer.
Animal Study [6]
Animal Models Male mdx (C57BL/10ScSn DMD mdx) mice
Formulation Dissolved in DMSO, and diluted in PBS
Doses ~10 μg/kg/day
Administration Injection
References
[1] Tsubuki S, et al. J Biochem, 1996, 119(3), 572-576.
[2] Fiedler MA, et al. Am J Respir Cell Mol Biol, 1998, 19(2), 259-268.
[3] Giuliano M, et al. Cancer Res, 1999, 59(21), 5586-5595.
[4] Arlt A, et al. Oncogene, 2001, 20(7), 859-868.
[5] MacLaren AP, et al. Cell Death Differ, 2001, 8(3), 210-218.
[6] Bonuccelli G, et al. Am J Pathol, 2003, 163(4), 1663-1675.
Sigma Aldrich - C2211 external link
Amino Acid Sequence
Z-Leu-Leu-Leu-al
Frequently Asked Questions
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Biochem/physiol Actions
Potent, membrane-permeable proteasome inhibitor. Induces neurite outgrowth in PC12 cells at 10 μM. Blocks cleavage of poly(ADP-ribose) polymerase and apoptosis in thymocytes. Proteasome inhibition induces accumulation of heat shock protein mRNA, activation of heat-shock proteins, and enhanced thermotolerance in various cell types: however, it also activates JNK-1, which initiates apoptosis in response to cell stress.

PATENTS

PATENTS

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INTERNET

INTERNET

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