(3S)-3-[(2S)-2-[(2S)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3-phenylpropanamido]propanamido]-5-fluoro-4-oxopentanoic acid

• ChemBase ID: 106524
• Molecular Formular: C27H36FN5O7S
• Molecular Mass: 593.6674432
• Monoisotopic Mass: 593.23194774
• SMILES: C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)C(=O)N[C@@H](CC(=O)O)C(=O)CF
• Canonical SMILES: FCC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)C)CC(=O)O
• InChI: InChI=1S/C27H36FN5O7S/c1-15(25(38)31-17(12-23(36)37)20(34)13-28)29-26(39)18(11-16-7-3-2-4-8-16)30-22(35)10-6-5-9-21-24-19(14-41-21)32-27(40)33-24/h2-4,7-8,15,17-19,21,24H,5-6,9-14H2,1H3,(H,29,39)(H,30,35)(H,31,38)(H,36,37)(H2,32,33,40)/t15-,17-,18-,19-,21-,24-/m0/s1
• InChIKey: YDCKNEYFIWYFGH-AJBHJIFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3-phenylpropanamido]propanamido]-5-fluoro-4-oxopentanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}-3-phenylpropanamido]propanamido]-5-fluoro-4-oxopentanoic acid
• Synonyms: Biotin-Phe-Ala-FMK; Biotin-F-A-FMK; Biotin-Phe-Ala-Fluoromethylketone

Database IDs

• PubChem SID: 162105711
• PubChem CID: 25108691

CALCULATED PROPERTIES

• Acid pKa: 4.1306753
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -1.2566508
• LogD (pH = 7.4): -2.951574
• Log P: 0.12785037
• Molar Refractivity: 146.1587 cm^3
• Polarizability: 57.0896 Å^3
• Polar Surface Area: 182.8 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03FK029C

An inhibitor/probe for Cathepsin B and L.

REFERENCES

• Esser, R. et al., J. of Rheumatology, 20(7):1176 (1993).
• Esser, R.E. et al., Arthritis Rheum., 37(21):236 (1994).