397100

HNMPA-(AM)₃

A cell-permeable analog of HNMPA that yields the parent compound upon cleavage by cytosolic esterases.

• Synonym(s): HNMPA-(AM)₃, Hydroxy-2-naphthalenylmethylphosphonic Acid Trisacetoxymethyl Ester, Pro-drug II
• Empirical Formula (Hill Notation): C₂₀H₂₃O₁₀P
• CAS Number: 120944-03-8
• Molecular Weight: 454.36
• MDL number: MFCD00236443
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (TLC)
• form: oil
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: colorless
• solubility: DMSO: 20 mg/mL; ethanol: 20 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: [P](=O)(OCOC(=O)C)(OCOC(=O)C)C(OCOC(=O)C)c1cc2c(cc1)cccc2
• InChI: 1S/C20H23O10P/c1-14(21)25-11-28-20(19-9-8-17-6-4-5-7-18(17)10-19)31(24,29-12-26-15(2)22)30-13-27-16(3)23/h4-10,20H,11-13H2,1-3H3
• InChI key: UQODAZKXEREJLZ-UHFFFAOYSA-N

Description

General description

A cell-permeable analog of HNMPA that yields the parent compound upon cleavage by cytosolic esterases. Inhibits insulin receptor tyrosine kinase (IC₅₀ = 100 µM) and insulin-stimulated glucose oxidation in isolated rat adipocytes (IC₅₀ = 10 µM). Also reported to inhibit tyrosine autophosphorylation of the human insulin receptor (IC₅₀ = 200 µM).

A cell-permeable analog of HNMPA. Inhibits insulin receptor tyrosine kinase (IC₅₀ = 100 mM) and insulin-stimulated glucose oxidation in isolated rat adipocytes (IC₅₀ = 10 µM). Also reported to inhibit tyrosine autophosphorylation of the human insulin receptor (IC₅₀ = 200 µM). It has no effect on PKA (at concentrations up to 1 mM) or PKC (at concentrations up to 420 µM).

Biochem/physiol Actions

Cell permeable: yes

Primary Target
tyrosine kinase

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 100 µM and 10 µM against insulin receptor tyrosine kinase and insulin-stimulated glucose oxidation in isolated rat adipocytes, respectively

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Baltensperger, K., et al. 1992. Proc. Natl. Acad. Sci. USA89, 7885.
Saperstein, R., et al. 1989. Biochemistry28, 5694.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable