Phosphoramidon

Phosphoramidon, a microbial metabolite, is a specific metalloprotease thermolysin inhibitor with an IC50 of 0.4 μg/mL. Phosphoramidon also inhibits endothelin-converting enzyme (ECE), neutral endopeptidase (NEP), and angiotensin-converting enzyme (ACE) with IC50 values of 3.5, 0.034, and 78 μM, respectively[1][2][3].

Product Specifications

CAS Number

[36357-77-4]

UNSPSC

12352005

Target

Angiotensin-converting Enzyme (ACE) ; Endogenous Metabolite; MMP; Neprilysin

Type

Natural Products

Related Pathways

Metabolic Enzyme/Protease

Applications

COVID-19-anti-virus

Field of Research

Cancer; Inflammation/Immunology; Cardiovascular Disease

Assay Protocol

https://www.medchemexpress.com/phosphoramidon.html

Solubility

10 mM in DMSO

Smiles

O[C@H]([C@@H]([C@H]([C@@H](O1)C)O)O)[C@@H]1OP(N[C@@H](CC(C)C)C(N[C@H](C(O)=O)CC2=CNC3=CC=CC=C23)=O)(O)=O

Molecular Formula

C23H34N3O10P

Molecular Weight

543.50

References & Citations

[1]Umezawa S, , et al. A new microbial metabolite phosphoramidon (isolation and structure) . Tetrahedron Letters, 1972, 13 (1) : 97-100.|[2]Suda H, et al. A thermolysin inhibitor produced by actinomycetes: phosphoramidon. The Journal of antibiotics, 1973, 26 (10) : 621-623.|[3]Kukkola PJ, et al. Differential structure-activity relationships of phosphoramidon analogues for inhibition of three metalloproteases: endothelin-converting enzyme, neutral endopeptidase, and angiotensin-converting enzyme.J CardiovascPharmacol. 1995;26Suppl 3:S65-8.|[4]Matsumura Y, et al. Phosphoramidon, a metalloproteinase inhibitor, suppresses the hypertensive effect of big endothelin-1. Eur J Pharmacol. 1990 Aug 21;185 (1) :103-6.|[5]McMahon EG, et al. Phosphoramidon blocks the pressor activity of porcine big endothelin-1- (1-39) in vivo and conversion of big endothelin-1- (1-39) to endothelin-1- (1-21) in vitro. Proc Natl Acad Sci U S A. 1991 Feb 1;88 (3) :703-7.