(2S)-2-[(2S)-2-aminopropanamido]-N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]propanamide

• ChemBase ID: 106475
• Molecular Formular: C16H22ClN3O3
• Molecular Mass: 339.81718
• Monoisotopic Mass: 339.13496926
• SMILES: C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)C(=O)CCl
• Canonical SMILES: ClCC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@@H](N)C)C
• InChI: InChI=1S/C16H22ClN3O3/c1-10(18)15(22)19-11(2)16(23)20-13(14(21)9-17)8-12-6-4-3-5-7-12/h3-7,10-11,13H,8-9,18H2,1-2H3,(H,19,22)(H,20,23)/t10-,11-,13-/m0/s1
• InChIKey: ONICONPPGVXITG-GVXVVHGQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-aminopropanamido]-N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]propanamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-aminopropanamido]-N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]propanamide
• Synonyms: Ala-Ala-Phe-CMK; AAF-CMK; Ala-Ala-Phe-Chloromethylketone

Database IDs

• PubChem SID: 162105988
• PubChem CID: 6610326

CALCULATED PROPERTIES

• Acid pKa: 11.84052
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.4293838
• LogD (pH = 7.4): 0.26269606
• Log P: 0.8715464
• Molar Refractivity: 88.0154 cm^3
• Polarizability: 34.62175 Å^3
• Polar Surface Area: 101.29 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03CK022

An inhibitor for Tripeptidyl Peptidase II.

REFERENCES

• Glas, R. et al., Nature, 392:618 (1998).
• Geier, E. et al., Science, 283:978 (1999).