benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(1S)-3-methyl-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butyl]carbamoyl}butyl]carbamoyl}butyl]carbamate

• ChemBase ID: 155692
• Molecular Formular: C36H48N4O7
• Molecular Mass: 648.78892
• Monoisotopic Mass: 648.3522999
• SMILES: Cc1cc(=O)oc2c1ccc(c2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)CC(C)C)NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C)C
• InChI: InChI=1S/C36H48N4O7/c1-21(2)15-28(33(42)37-26-13-14-27-24(7)18-32(41)47-31(27)19-26)38-34(43)29(16-22(3)4)39-35(44)30(17-23(5)6)40-36(45)46-20-25-11-9-8-10-12-25/h8-14,18-19,21-23,28-30H,15-17,20H2,1-7H3,(H,37,42)(H,38,43)(H,39,44)(H,40,45)/t28-,29-,30-/m0/s1
• InChIKey: MBZJQSNQQJWUBH-DTXPUJKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(1S)-3-methyl-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butyl]carbamoyl}butyl]carbamoyl}butyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(1S)-3-methyl-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]butyl]carbamoyl}butyl]carbamoyl}butyl]carbamate
• Synonyms: Cbz-Leu-Leu-Leu-AMC; Z-LLL-AMC; Z-Leu-Leu-Leu-7-amido-4-methylcoumarin

Database IDs

• MDL Number: MFCD01074988
• PubChem SID: 162249830
• PubChem CID: 21121681

CALCULATED PROPERTIES

• Acid pKa: 12.002884
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 5.8170023
• LogD (pH = 7.4): 5.8169928
• Log P: 5.8170023
• Molar Refractivity: 179.8428 cm^3
• Polarizability: 69.49594 Å^3
• Polar Surface Area: 151.93 Å^2
• Rotatable Bonds: 16
• 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% (HPLC and TLC)
• Empirical Formula (Hill Notation): C36H48N4O7

DETAILS

Sigma Aldrich - C0608

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