methyl (3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]propanamido]-5-chloro-4-oxopentanoate

• ChemBase ID: 106479
• Molecular Formular: C20H26ClN3O7
• Molecular Mass: 455.88934
• Monoisotopic Mass: 455.14592787
• SMILES: COC(=O)C[C@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)OCc1ccccc1)C(=O)CCl
• Canonical SMILES: COC(=O)C[C@@H](C(=O)CCl)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C)C
• InChI: InChI=1S/C20H26ClN3O7/c1-12(19(28)24-15(16(25)10-21)9-17(26)30-3)22-18(27)13(2)23-20(29)31-11-14-7-5-4-6-8-14/h4-8,12-13,15H,9-11H2,1-3H3,(H,22,27)(H,23,29)(H,24,28)/t12-,13-,15-/m0/s1
• InChIKey: QMNQUIKZKYBZII-YDHLFZDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]propanamido]-5-chloro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]propanamido]-5-chloro-4-oxopentanoate
• Synonyms: Z-Ala-Ala-Asp(OMe)-CMK; Z-AAD(OMe)-CMK; Z-Ala-Ala-Asp(OMe)-Chloromethylketone; Z-Ala-Ala-Asp(OMe)-chloromethyl ketone

Database IDs

• MDL Number: MFCD03452874
• PubChem SID: 162105704
• PubChem CID: 25108658

CALCULATED PROPERTIES

• Acid pKa: 11.426222
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.8819126
• LogD (pH = 7.4): 0.8818768
• Log P: 0.881913
• Molar Refractivity: 109.8809 cm^3
• Polarizability: 43.292507 Å^3
• Polar Surface Area: 139.9 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

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

Product Information

• Purity: ≥98% (TLC)
• Empirical Formula (Hill Notation): C20H26N3O7Cl

DETAILS

MP Biomedicals - 03CK032

An inhibitor for Granzyme B.

Sigma Aldrich - C0235

Application
Cell permeable Granzyme B inhibitor peptide.

REFERENCES

• Deas, O. et al., J. Imm., 161:3375 (1998).
• Ponk, G.J., et al., Science, 271:808 (1996).