(4-carbamimidoylphenyl)methanesulfonyl fluoride hydrochloride

• ChemBase ID: 105884
• Molecular Formular: C8H10ClFN2O2S
• Molecular Mass: 252.6936032
• Monoisotopic Mass: 252.01355447
• SMILES: Cl.NC(=N)c1ccc(CS(=O)(=O)F)cc1
• Canonical SMILES: NC(=N)c1ccc(cc1)CS(=O)(=O)F.Cl
• InChI: InChI=1S/C8H9FN2O2S.ClH/c9-14(12,13)5-6-1-3-7(4-2-6)8(10)11;/h1-4H,5H2,(H3,10,11);1H
• InChIKey: KHLLRHIUKOJXLL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-carbamimidoylphenyl)methanesulfonyl fluoride hydrochloride
• IUPAC Traditional name: (4-carbamimidoylphenyl)methanesulfonyl fluoride hydrochloride
• Synonyms: 4-Amidinobenzylsulfonyl fluoride hydrochloride; 4-Amidinophenylmethanesulfonyl fluoride hydrochloride; p-APMSF; p-AMIDINOPHENYLMETHYLSULFONYLFLUORIDE HYDROCHLORIDE

Database IDs

• CAS Number: 74938-88-8
• MDL Number: MFCD00078902
• Beilstein Number: 9083148
• PubChem SID: 24891118; 162092637
• PubChem CID: 16218950

CALCULATED PROPERTIES

• Acid pKa: 18.330584
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.1007767
• LogD (pH = 7.4): -2.0916345
• Log P: 0.31456432
• Molar Refractivity: 61.8771 cm^3
• Polarizability: 19.854534 Å^3
• Polar Surface Area: 84.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~205 °C (dec.)

Safety Information

• Storage Condition: 2-8°C
• 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: >75%; ≥97.0% (AT)
• Empirical Formula (Hill Notation): C8H9FN2O2S · HCl

DETAILS

MP Biomedicals - 02194956

Hydrochloride
Purity: >75%
A stable, non-toxic alternative to DFP or PMSF. Specifically and irreversibly inhibits trypsin-like serine proteases, trypsin, and thrombin. Demonstrates activity on factor Xa, plasmin, C1r and C1s. Activity is 1000 fold greater than PMSF.

Sigma Aldrich - 06566

Other Notes
An irreversible inhibitor of serine proteases4
Application
APMSF was used to study the glucagon-receptor interaction; inhibition of cAMP formation led to the conclusion that there was a previously unexpected serine residue in the active site which may operate on the receptor by a mechanism similar to serine proteases.1
Biochem/physiol Actions
Irreversible inhibitor of serine proteases with lysine or arginine substrate specificities. Effective concentration 10-100 μM. Frequently used to characterize newly discovered proteases.2,3

REFERENCES

• Cole, T.C., et al., Biochim. Biophys. Acta , 990 : 254, (1989).