6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexyl propan-2-yl fluorophosphonate

• ChemBase ID: 162098
• Molecular Formular: C19H35FN3O5PS
• Molecular Mass: 467.5354642
• Monoisotopic Mass: 467.20190709
• SMILES: N1C(=O)N[C@@H]2[C@@H](SC[C@H]12)CCCCC(=O)NCCCCCCOP(=O)(OC(C)C)F
• Canonical SMILES: O=C(CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)NCCCCCCOP(=O)(OC(C)C)F
• InChI: InChI=1S/C19H35FN3O5PS/c1-14(2)28-29(20,26)27-12-8-4-3-7-11-21-17(24)10-6-5-9-16-18-15(13-30-16)22-19(25)23-18/h14-16,18H,3-13H2,1-2H3,(H,21,24)(H2,22,23,25)/t15-,16-,18-,29?/m0/s1
• InChIKey: KDPHOPZAOAVYRV-VTNPVEBBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexyl propan-2-yl fluorophosphonate
• IUPAC Traditional name: 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}hexyl isopropyl fluorophosphonate
• Synonyms: 6-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]amino]hexyl Phosphorofluoridic Acid 1-Methylethyl Ester Hemihydrate; 6-N-Biotinylaminohexyl Isopropyl Phosphorofluoridate, Hemihydrate

Database IDs

• CAS Number: 353754-93-5
• PubChem SID: 162256233
• PubChem CID: 10647947

CALCULATED PROPERTIES

• Acid pKa: 13.485911
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.0180979
• LogD (pH = 7.4): 2.0180993
• Log P: 2.0180995
• Molar Refractivity: 115.2334 cm^3
• Polarizability: 45.442265 Å^3
• Polar Surface Area: 105.76 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Orange Waxy Solid
• Melting Point: 124-126°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B394900

A potent tool for the inhibition and isolation of Serine Esterases and Proteases. Also a potent inhibitor of a-chymotrypsin.

REFERENCES

• Cohen, J., et al.: Meth. Enzymol., 11, 686 (1967)
• DelMar, E., et al.: Anal. Biochem., 99, 316 (1967)
• Fukuda, Y., et al.: Eur. J. Pharmacol., 390, 203 (1967)
• Davies, S., et al.: J. Biol. Chem., 276, 16015 (1967)
• Quistad, G., et al.: Toxicol. Appl. Phar