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

• ChemBase ID: 106508
• Molecular Formular: C30H49FN6O8S
• Molecular Mass: 672.8088632
• Monoisotopic Mass: 672.33166178
• SMILES: COC(=O)C[C@H](NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)CCCCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)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)CCCCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)C
• InChI: InChI=1S/C30H49FN6O8S/c1-17(2)26(29(43)33-18(3)28(42)34-19(21(38)15-31)14-25(41)45-4)36-24(40)12-6-5-9-13-32-23(39)11-8-7-10-22-27-20(16-46-22)35-30(44)37-27/h17-20,22,26-27H,5-16H2,1-4H3,(H,32,39)(H,33,43)(H,34,42)(H,36,40)(H2,35,37,44)/t18-,19-,20-,22-,26-,27-/m0/s1
• InChIKey: MOQLQMKJGYKHCT-VRKQFSAKSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105624
• PubChem CID: 25108682

CALCULATED PROPERTIES

• Acid pKa: 11.645396
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -0.18556158
• LogD (pH = 7.4): -0.1855806
• Log P: -0.18555869
• Molar Refractivity: 166.7643 cm^3
• Polarizability: 65.56319 Å^3
• Polar Surface Area: 200.9 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03FK014

An inhibitor/probe for General Caspases. Biotinylated derivative of Z-VAD(OMe)-FMK that may be used to identify active caspases in cell lysates. There is a linker molecule (epsilon-AMINO-N-CAPROIC ACID) between biotin and the peptide.

REFERENCES

• Bombeck, C.A. et al., J. Biol. Chem., 274(24):17325 (1999).
• Li, S. et al. 1999. J. Biol. Chem. 274, 17325.
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.