methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(2S)-4-chloro-3-oxobutan-2-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate

• ChemBase ID: 106470
• Molecular Formular: C20H31ClN4O7
• Molecular Mass: 474.93574
• Monoisotopic Mass: 474.18812703
• SMILES: COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)CCl
• Canonical SMILES: COC(=O)CCC(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)CCl)C)C)C
• InChI: InChI=1S/C20H31ClN4O7/c1-11(15(26)10-21)23-19(30)14-6-5-9-25(14)20(31)13(3)24-18(29)12(2)22-16(27)7-8-17(28)32-4/h11-14H,5-10H2,1-4H3,(H,22,27)(H,23,30)(H,24,29)/t11-,12-,13-,14-/m0/s1
• InChIKey: UIYRKMRXXFXSTH-XUXIUFHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(2S)-4-chloro-3-oxobutan-2-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate
• IUPAC Traditional name: methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(2S)-4-chloro-3-oxobutan-2-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate
• Synonyms: MeOSuc-Ala-Ala-Pro-Ala-CMK; MeOSuc-AAPA-CMK; MeOSuc-Ala-Ala-Pro-Ala-Chloromethylketone

Database IDs

• PubChem SID: 162105472
• PubChem CID: 10390162

CALCULATED PROPERTIES

• Acid pKa: 11.796004
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.2590302
• LogD (pH = 7.4): -1.2590455
• Log P: -1.25903
• Molar Refractivity: 113.4891 cm^3
• Polarizability: 44.614067 Å^3
• Polar Surface Area: 150.98 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03CK017

An inhibitor for Neutrophil Elastase.

REFERENCES

• Navia, et al., Proc. Nat. Acad. Sci. USA, 86:7 (1989).