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Literature summary for 2.3.1.122 extracted from

  • Gobec, S.; Plantan, I.; Mravljak, J.; Svajger, U.; Wilson, R.A.; Besra, G.S.; Soares, S.L.; Appelberg, R.; Kikelj, D.
    Design, synthesis, biochemical evaluation and antimycobacterial action of phosphonate inhibitors of antigen 85C, a crucial enzyme involved in biosynthesis of the mycobacterial cell wall (2007), Eur. J. Med. Chem., 42, 54-63.
    View publication on PubMed
Search for more literature for 2.3.1.122

Inhibitors

Inhibitors Comment Organism Structure
(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-methyl ethyl butylphosphonate IC50: 0.010 mM Mycobacterium avium
(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-methyl ethyl tetradecylphosphonate IC50: 0.0410 mM Mycobacterium avium
(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl ethyl heptylphosphonate IC50: 0.0013 mM Mycobacterium avium
(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl ethyl nonylphosphonate IC50: 0.0871 mM Mycobacterium avium
2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-ethyl ethyl butylphosphonate IC50: 0.0507 mM Mycobacterium avium
2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-ethyl ethyl nonylphosphonate IC50: 0.0257 mM Mycobacterium avium
2-phenylethanol
-
 Mycobacterium avium
3,4,5-trimethoxybenzylphosphonate IC50: 0.102 mM Mycobacterium avium
4-(phthalimido)butanol
-
 Mycobacterium avium
ethyl 3-phenoxybenzyl butylphosphonate IC50: 0.002 mM Mycobacterium avium
ethyl 3-phenoxybenzyl heptylphosphonate IC50: 0.021 mM Mycobacterium avium
ethyl 3-phenoxybenzyl hexylphosphonate IC50: 0.0426 mM Mycobacterium avium
ethyl 3-phenoxybenzyl nonylphosphonate IC50: 0.0148 mM Mycobacterium avium
ethyl 3-phenoxybenzyl tetradecylphosphonate IC50: 0.862 mM Mycobacterium avium
ethyl hydrogen 2-phenylethyl phosphonate IC50: 0.225 mM Mycobacterium avium
ethyl hydrogen 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butylphosphonate IC50: 0.110 mM Mycobacterium avium
ethyl hydrogen butylphosphonate IC50: 0.431 mM Mycobacterium avium
ethyl hydrogen heptylphosphonate IC50: 0.0011 mM Mycobacterium avium
ethyl hydrogen hexylphosphonate IC50: 0.0036 mM Mycobacterium avium
ethyl hydrogen nonylphosphonate IC50: 0.471 mM Mycobacterium avium
additional information design of mechanism-based inhibitors, growth inhibition assay, molecular docking, overview Mycobacterium avium
N-(omega-hydroxyalky)phthalimide
-
 Mycobacterium avium

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
alpha,alpha-trehalose 6-mycolate Mycobacterium avium
-
 alpha,alpha-trehalose + alpha,alpha-trehalose 6,6'-bismycolate
-
 ?

Organism

Organism UniProt Comment Textmining
Mycobacterium avium
-
-
-

Reaction

Reaction Comment Organism Reaction ID
2 alpha,alpha-trehalose 6-mycolate = alpha,alpha-trehalose + alpha,alpha-trehalose 6,6'-bismycolate reaction mechanism via enzyme complexed with the tetrahedral transition state and mycolic acid covalently attached to the enzyme, the catalytic triad is formed by Ser124, Glu228 and His260 Mycobacterium avium
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
alpha,alpha-trehalose 6-mycolate
-
 Mycobacterium avium alpha,alpha-trehalose + alpha,alpha-trehalose 6,6'-bismycolate
-
 ?

Synonyms

Synonyms Comment Organism
ag85C
-
 Mycobacterium avium
antigen 85C
-
 Mycobacterium avium
mycolyltransferase
-
 Mycobacterium avium

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Mycobacterium avium

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Mycobacterium avium

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0011
-
 IC50: 0.0011 mM Mycobacterium avium ethyl hydrogen heptylphosphonate
0.0013
-
 IC50: 0.0013 mM Mycobacterium avium (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl ethyl heptylphosphonate
0.002
-
 IC50: 0.002 mM Mycobacterium avium ethyl 3-phenoxybenzyl butylphosphonate
0.0036
-
 IC50: 0.0036 mM Mycobacterium avium ethyl hydrogen hexylphosphonate
0.01
-
 IC50: 0.010 mM Mycobacterium avium (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-methyl ethyl butylphosphonate
0.0148
-
 IC50: 0.0148 mM Mycobacterium avium ethyl 3-phenoxybenzyl nonylphosphonate
0.021
-
 IC50: 0.021 mM Mycobacterium avium ethyl 3-phenoxybenzyl heptylphosphonate
0.0257
-
 IC50: 0.0257 mM Mycobacterium avium 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-ethyl ethyl nonylphosphonate
0.041
-
 IC50: 0.0410 mM Mycobacterium avium (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-methyl ethyl tetradecylphosphonate
0.0426
-
 IC50: 0.0426 mM Mycobacterium avium ethyl 3-phenoxybenzyl hexylphosphonate
0.0507
-
 IC50: 0.0507 mM Mycobacterium avium 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-ethyl ethyl butylphosphonate
0.0871
-
 IC50: 0.0871 mM Mycobacterium avium (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl ethyl nonylphosphonate
0.102
-
 IC50: 0.102 mM Mycobacterium avium 3,4,5-trimethoxybenzylphosphonate
0.11
-
 IC50: 0.110 mM Mycobacterium avium ethyl hydrogen 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butylphosphonate
0.225
-
 IC50: 0.225 mM Mycobacterium avium ethyl hydrogen 2-phenylethyl phosphonate
0.431
-
 IC50: 0.431 mM Mycobacterium avium ethyl hydrogen butylphosphonate
0.471
-
 IC50: 0.471 mM Mycobacterium avium ethyl hydrogen nonylphosphonate
0.862
-
 IC50: 0.862 mM Mycobacterium avium ethyl 3-phenoxybenzyl tetradecylphosphonate