(3S)-7-amino-1-chloro-S-(4-methylphenyl)-2-oxoheptane-3-sulfonamido

• ChemBase ID: 6211
• Molecular Formular: C14H21ClN2O3S
• Molecular Mass: 332.84614
• Monoisotopic Mass: 332.09614122
• SMILES: S(=O)(=O)(c1ccc(cc1)C)N[C@H](C(=O)CCl)CCCCN
• Canonical SMILES: NCCCC[C@@H](C(=O)CCl)NS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C14H21ClN2O3S/c1-11-5-7-12(8-6-11)21(19,20)17-13(14(18)10-15)4-2-3-9-16/h5-8,13,17H,2-4,9-10,16H2,1H3/t13-/m0/s1
• InChIKey: RDFCSSHDJSZMTQ-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-7-amino-1-chloro-S-(4-methylphenyl)-2-oxoheptane-3-sulfonamido
• IUPAC Traditional name: C14H21ClN2O3S
• Synonyms: N-[(1S)-5-amino-1-(chloroacetyl)pentyl]-4-methylbenzenesulfonamide; Tosyl-Lys-CMK; Tosyl-K-CMK; Tosyl-Lys-Chloromethylketone

Database IDs

• PubChem SID: 160969636; 99445074
• PubChem CID: 73094

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.525673
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.9197374
• LogD (pH = 7.4): -0.3531182
• Log P: 1.684215
• Molar Refractivity: 84.3488 cm^3
• Polarizability: 33.71932 Å^3
• Polar Surface Area: 89.26 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.82
• LOG S: -3.78
• Solubility (Water): 5.50e-02 g/l

DETAILS

MP Biomedicals - 03CK004

Inhibits trypsin-like serine proteinases. Irreversibly inactivates trypsin without affecting chymotrypsin. Prevents nitric oxide production by activated macrophages by interfering with transcription of the iNOS gene. Blocks cell-cell adhesion and binding of HIV-1 virus to the target cells. In macrophages, blocks nitric oxide synthase induced by interferon-g and lipopolysaccharides (EC₅₀ = 80 μM). Prevents endonucleolysis accompanying apoptotic death of HL-60 leukemia cells and normal thymocytes.

DrugBank - DB08603

Drug information: experimental

REFERENCES

• Griscavage, J.M., et al. 1995. Biochem. Biophys. Res. Commun. 215, 721.
• Kim, H., et al. 1995. J. Immunol. 154, 4741.
• Bourinbaiar, A.S. and Nagorny, R. 1994. Cell Immunol. 155, 230.
• Biro, A., et al. 1992. Eur. J. Immunol. 22, 2547.
• Bruno, S., et al. 1992. Leukemia 6, 1113.
• Lee, S.F. 1992. Infect. Immun. 60, 4032.
• Schmidt, H.H., et al. 1992. Mol. Pharmacol. 41, 615.