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

• ChemBase ID: 106342
• Molecular Formular: C30H41F3N4O6
• Molecular Mass: 610.6649496
• Monoisotopic Mass: 610.29781971
• SMILES: CC(C)C[C@H](NC(=O)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: CC(C[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(C)C)CC(C)C)C
• InChI: InChI=1S/C30H41F3N4O6/c1-15(2)10-22(34-18(7)38)28(41)37-24(12-17(5)6)29(42)36-23(11-16(3)4)27(40)35-19-8-9-20-21(30(31,32)33)14-26(39)43-25(20)13-19/h8-9,13-17,22-24H,10-12H2,1-7H3,(H,34,38)(H,35,40)(H,36,42)(H,37,41)/t22-,23-,24-/m0/s1
• InChIKey: MHIJTPMBJGOLKE-HJOGWXRNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-acetamido-4-methyl-N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}butyl]pentanamide
• IUPAC Traditional name: (2S)-2-acetamido-4-methyl-N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}butyl]pentanamide
• Synonyms: Ac-Leu-Leu-Leu-AFC; Ac-LLL-AFC; Ac-Leu-Leu-Leu-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105957
• PubChem CID: 25108562

CALCULATED PROPERTIES

• Acid pKa: 11.731521
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.8376648
• LogD (pH = 7.4): 3.8376472
• Log P: 3.837665
• Molar Refractivity: 154.5391 cm^3
• Polarizability: 58.528385 Å^3
• Polar Surface Area: 142.7 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC119

A fluorogenic substrate for Proteosomes.

REFERENCES

• Tsubuki, S., et al., Biochem. Biophys. Res. Comm., 196:1195 (1993).