(4S)-4-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-4-methylpentanamido]-4-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butanoic acid

• ChemBase ID: 106455
• Molecular Formular: C35H44N4O9
• Molecular Mass: 664.74526
• Monoisotopic Mass: 664.31082901
• SMILES: CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)CCC(=O)O)NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C)C
• InChI: InChI=1S/C35H44N4O9/c1-20(2)15-27(38-34(45)28(16-21(3)4)39-35(46)47-19-23-9-7-6-8-10-23)33(44)37-26(13-14-30(40)41)32(43)36-24-11-12-25-22(5)17-31(42)48-29(25)18-24/h6-12,17-18,20-21,26-28H,13-16,19H2,1-5H3,(H,36,43)(H,37,44)(H,38,45)(H,39,46)(H,40,41)/t26-,27-,28-/m0/s1
• InChIKey: FOYHOBVZPWIGJM-KCHLEUMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-4-methylpentanamido]-4-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-4-methylpentanamido]-4-[(4-methyl-2-oxochromen-7-yl)carbamoyl]butanoic acid
• Synonyms: Z-Leu-Leu-Glu-AMC; Z-LLE-AMC; Z-Leu-Leu-Glu-7-Amino-4-Methylcoumarin; Cbz-Leu-Leu-Glu-AMC; Z-Leu-Leu-Glu-7-amido-4-methylcoumarin

Database IDs

• MDL Number: MFCD01074989
• PubChem SID: 162105701
• PubChem CID: 25108642

CALCULATED PROPERTIES

• Acid pKa: 3.7074356
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 2.418118
• LogD (pH = 7.4): 0.9072664
• Log P: 4.2097416
• Molar Refractivity: 176.9596 cm^3
• Polarizability: 68.23021 Å^3
• Polar Surface Area: 189.23 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• Apperance: solid

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%
• Empirical Formula (Hill Notation): C35H44N4O9

DETAILS

MP Biomedicals - 03AMC180

A fluorogenic Proteosome substrate measuring Peptidylglutamyl Peptide hydrolyzing activity of the 20 I Proteosome.

Sigma Aldrich - C0483

Amino Acid Sequence
Z-Leu-Leu-Glu-AMC
General description
Manufactured for Sigma by Boston Biochem., Inc.
Biochem/physiol Actions
Fluorogenic substrate for the measurement of the peptidylglutamyl-peptide hydrolyzing activity of the 20S proteasome.

REFERENCES

• Crain, et al., J. Biol. Chem., 272(20):13437 (1997).
• Lono, P.O. et al., Immunopharm., 36:285 (1997).
• Orlowski, M. et al., Biochem., 32:1563 (1993).