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
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About This Item
Empirical Formula (Hill Notation):
C20H23O10P
CAS Number:
Molecular Weight:
454.36
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
Quality Level
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
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
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
Preparation Note
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.
Saperstein, R., et al. 1989. Biochemistry28, 5694.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
Storage Class
10 - Combustible liquids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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