(3S)-3-[(2S,3R)-2-[(2S)-2-[(2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-methylpentanamido]-4-carboxybutanamido]-3-hydroxybutanamido]-5-fluoro-4-oxopentanoic acid

• ChemBase ID: 155442
• Molecular Formular: C28H39FN4O11
• Molecular Mass: 626.6278632
• Monoisotopic Mass: 626.25993631
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(=O)O)C(=O)CF)NC(=O)OCc1ccccc1
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)CF)CC(=O)O)[C@H](O)C)CCC(=O)O)NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C28H39FN4O11/c1-4-15(2)23(33-28(43)44-14-17-8-6-5-7-9-17)26(41)30-18(10-11-21(36)37)25(40)32-24(16(3)34)27(42)31-19(12-22(38)39)20(35)13-29/h5-9,15-16,18-19,23-24,34H,4,10-14H2,1-3H3,(H,30,41)(H,31,42)(H,32,40)(H,33,43)(H,36,37)(H,38,39)/t15-,16+,18-,19-,23-,24-/m0/s1
• InChIKey: CTXDBLYOEUERAT-VUVYEONESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S,3R)-2-[(2S)-2-[(2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-methylpentanamido]-4-carboxybutanamido]-3-hydroxybutanamido]-5-fluoro-4-oxopentanoic acid
• IUPAC Traditional name: (3S)-3-[(2S,3R)-2-[(2S)-2-[(2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-methylpentanamido]-4-carboxybutanamido]-3-hydroxybutanamido]-5-fluoro-4-oxopentanoic acid
• Synonyms: Z-IETD-FMK; Z-Ile-Glu(O-ME)-Thr-Asp(O-Me) fluoromethyl ketone

Database IDs

• MDL Number: MFCD01861686
• PubChem SID: 162249580
• PubChem CID: 9852146

CALCULATED PROPERTIES

• Log P: 0.08457813
• Molar Refractivity: 148.0156 cm^3
• Polarizability: 58.187233 Å^3
• Polar Surface Area: 237.53 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false
• Acid pKa: 3.7692652
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -2.790789
• LogD (pH = 7.4): -6.142088

PROPERTIES

Physical Property

• Apperance: powder

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)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C30H43FN4O11

DETAILS

Sigma Aldrich - C1230

Amino Acid Sequence
Z-Ile-Glu-OMe-Thr-Asp-OMe-FMK
Application
Cell-permeable inhibitor of caspase-8, which exhibits competitive and irreversible inhibition.