methyl (3S)-3-[(2S)-6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]hexanamido]-5-fluoro-4-oxopentanoate

• ChemBase ID: 106521
• Molecular Formular: C35H51FN6O9S
• Molecular Mass: 750.8776432
• Monoisotopic Mass: 750.34222646
• SMILES: COC(=O)C[C@H](NC(=O)[C@H](CCCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)CF
• Canonical SMILES: COC(=O)C[C@@H](C(=O)CF)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1)CCCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C35H51FN6O9S/c1-21(2)30(42-35(49)51-19-22-11-5-4-6-12-22)33(47)38-23(32(46)39-24(26(43)18-36)17-29(45)50-3)13-9-10-16-37-28(44)15-8-7-14-27-31-25(20-52-27)40-34(48)41-31/h4-6,11-12,21,23-25,27,30-31H,7-10,13-20H2,1-3H3,(H,37,44)(H,38,47)(H,39,46)(H,42,49)(H2,40,41,48)/t23-,24-,25-,27-,30-,31-/m0/s1
• InChIKey: LMOBAYUYTBCJGZ-MAOMSRCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S)-6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]hexanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S)-6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]hexanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Val-Lys(Biotin)-Asp(OMe)-FMK; Z-VL(Biotin)D(OMe)-FMK; Z-Val-Lys(Biotin)-Asp(OMe)-Fluoromethylketone

Database IDs

• PubChem SID: 162105508
• PubChem CID: 25108690

CALCULATED PROPERTIES

• Acid pKa: 11.646594
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): 1.5356215
• LogD (pH = 7.4): 1.5356016
• Log P: 1.5356234
• Molar Refractivity: 188.2966 cm^3
• Polarizability: 73.96721 Å^3
• Polar Surface Area: 210.13 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03FK027

An inhibitor for General Caspases.

REFERENCES

• Armstrong, R.C. et al., J. Neurosci., 17(2):553 (1997).