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

• ChemBase ID: 106473
• Molecular Formular: C22H35ClN4O7
• Molecular Mass: 502.9889
• Monoisotopic Mass: 502.21942716
• 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)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)C)C
• InChI: InChI=1S/C22H35ClN4O7/c1-12(2)19(16(28)11-23)26-21(32)15-7-6-10-27(15)22(33)14(4)25-20(31)13(3)24-17(29)8-9-18(30)34-5/h12-15,19H,6-11H2,1-5H3,(H,24,29)(H,25,31)(H,26,32)/t13-,14-,15-,19-/m0/s1
• InChIKey: PJGDFLJMBAYGGC-XLPNERPQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(3S)-1-chloro-4-methyl-2-oxopentan-3-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate
• IUPAC Traditional name: methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(3S)-1-chloro-4-methyl-2-oxopentan-3-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate
• Synonyms: N-(Methoxysuccinyl)-L-alanyl-L-alanyl-L-prolyl-L-valine chloromethylketone; N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone; MeOSuc-Ala-Ala-Pro-Val-CMK; MeOSuc-AAPV-CMK; MeOSuc-Ala-Ala-Pro-Val-Chloromethylketone

Database IDs

• CAS Number: 65144-34-5
• MDL Number: MFCD00077136
• Beilstein Number: 6167019
• PubChem SID: 24896552; 162087703
• PubChem CID: 5486692

CALCULATED PROPERTIES

• Acid pKa: 11.829253
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.37153497
• LogD (pH = 7.4): -0.3715491
• Log P: -0.37153476
• Molar Refractivity: 122.4847 cm^3
• Polarizability: 48.25446 Å^3
• Polar Surface Area: 150.98 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

MP Biomedicals - 03CK020

An inhibitor for Human Leukocyte Elastase.

Sigma Aldrich - M0398

Biochem/physiol Actions
Irreversible inhibitor of human leukocyte1 and neutrophil2 elastase.

REFERENCES

• Powers, J.C. et al., Biochem. Biophys. Acta., 485:156 (1977).
• Stein, R.L. and Trainor, D.A., Biochem., 25:5414 (1986).