methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]-5-fluoro-4-oxopentanoate

• ChemBase ID: 106528
• Molecular Formular: C28H39FN4O10
• Molecular Mass: 610.6284632
• Monoisotopic Mass: 610.26502169
• SMILES: COC(=O)CC[C@H](NC(=O)[C@H](C)NC(=O)OCc1ccccc1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)OC)C(=O)CF
• Canonical SMILES: COC(=O)CC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)CF)CC(=O)OC)C(C)C)NC(=O)[C@@H](NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C28H39FN4O10/c1-16(2)24(27(39)32-20(21(34)14-29)13-23(36)42-5)33-26(38)19(11-12-22(35)41-4)31-25(37)17(3)30-28(40)43-15-18-9-7-6-8-10-18/h6-10,16-17,19-20,24H,11-15H2,1-5H3,(H,30,40)(H,31,37)(H,32,39)(H,33,38)/t17-,19-,20-,24-/m0/s1
• InChIKey: CHZRBQFKZDGMTP-CDSYHYPYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Ala-Glu(OMe)-Val-Asp(OMe)-FMK; Z-A-E(OMe)-V-Asp(OMe)-FMK; Z-Ala-Glu(OMe)-Val-Asp(OMe)-Fluoromethylketone; Z-AEVD-FMK; Z-Ala-Glu(OMe)-Val-Asp(OMe)-fluoromethyl ketone

Database IDs

• MDL Number: MFCD03453601
• PubChem SID: 162105712
• PubChem CID: 25108694

CALCULATED PROPERTIES

• Acid pKa: 11.410198
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.56213206
• LogD (pH = 7.4): 0.5620949
• Log P: 0.56213254
• Molar Refractivity: 146.9903 cm^3
• Polarizability: 57.971127 Å^3
• Polar Surface Area: 195.3 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white 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: ≥90% (TLC)
• Empirical Formula (Hill Notation): C28H39N4O10F

DETAILS

MP Biomedicals - 03FK033

An inhibitor for Caspase-6 and 8.

Sigma Aldrich - C8484

Amino Acid Sequence
Z-Ala-Glu(OMe)-Val-Asp(OMe)-FMK
Application
Caspase inhibitor.

REFERENCES

• Garcia-Calvo, M. et al., J. Biol. Chem., 273(49):32608 (1998).