methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-5-methoxy-5-oxopentanamido]-3-(1H-imidazol-4-yl)propanamido]-5-fluoro-4-oxopentanoate

• ChemBase ID: 106516
• Molecular Formular: C32H43FN6O10
• Molecular Mass: 690.7164232
• Monoisotopic Mass: 690.30246983
• SMILES: COC(=O)CC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1c[nH]cn1)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)Cc1nc[nH]c1)NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C
• InChI: InChI=1S/C32H43FN6O10/c1-19(2)12-24(39-32(46)49-17-20-8-6-5-7-9-20)30(44)36-22(10-11-27(41)47-3)29(43)38-25(13-21-16-34-18-35-21)31(45)37-23(26(40)15-33)14-28(42)48-4/h5-9,16,18-19,22-25H,10-15,17H2,1-4H3,(H,34,35)(H,36,44)(H,37,45)(H,38,43)(H,39,46)/t22-,23-,24-,25-/m0/s1
• InChIKey: YXRKBEPGVHOXSV-QORCZRPOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-5-methoxy-5-oxopentanamido]-3-(1H-imidazol-4-yl)propanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-5-methoxy-5-oxopentanamido]-3-(1H-imidazol-4-yl)propanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Leu-Glu(OMe)-His-Asp(OMe)-FMK; Z-LE(OMe)HD(OMe)-FMK; Z-Leu-Glu(OMe)-His-Asp(OMe)-Fluoromethylketone; Z-LEHD-FMK; Z-Leu-Glu(O-Me)-His-Asp(O-Me) fluoromethyl ketone trifluoroacetate salt hydrate

Database IDs

• MDL Number: MFCD01862609
• PubChem SID: 162105584
• PubChem CID: 10032582

CALCULATED PROPERTIES

• Acid pKa: 11.289476
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.28587946
• LogD (pH = 7.4): 0.44610298
• Log P: 0.4964272
• Molar Refractivity: 168.6643 cm^3
• Polarizability: 66.211205 Å^3
• Polar Surface Area: 223.98 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: off-white to tan powder

Safety Information

• Storage Condition: desiccated
• 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%
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C32H43FN6O10 · xC2HF3O2 · yH2O

DETAILS

MP Biomedicals - 03FK022

A potent, cell-permeable, and irreversible inhibitor of caspase-9. May also inhibit caspase-4 and caspase-5. When using with purified native or recombinant enzyme, pretreatment with an esterase is required.

Sigma Aldrich - C1355

Application
A cell-permeable inhibitor of caspase-9, which exhibits competitive and irreversible inhibition.

REFERENCES

• Gamen, S. et al., Exp. Cell. Res., 258(1):223 (2000).
• Fadeel, B., et al. 1999. Leukemia 13, 719.
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.