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Merck

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:
120944-03-8
Molecular Weight:
454.36
MDL number:
MFCD00236443
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

HNMPA-(AM)3, A cell-permeable analog of HNMPA that yields the parent compound upon cleavage by cytosolic esterases.

InChI key

UQODAZKXEREJLZ-UHFFFAOYSA-N

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

SMILES string

[P](=O)(OCOC(=O)C)(OCOC(=O)C)C(OCOC(=O)C)c1cc2c(cc1)cccc2

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

Quality Level

100

Related Categories

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

Disclaimer

Toxicity: Standard Handling (A)

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).

Other Notes

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

Preparation Note

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

Legal Information

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

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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