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Literature summary for 1.1.1.205 extracted from

  • Watkins, W.J.; Chen, J.M.; Cho, A.; Chong, L.; Collins, N.; Fardis, M.; Huang, W.; Hung, M.; Kirschberg, T.; Lee, W.A.; Liu, X.; Thomas, W.; Xu, J.; Zeynalzadegan, A.; Zhang, J.
    Phosphonic acid-containing analogues of mycophenolic acid as inhibitors of IMPDH (2006), Bioorg. Med. Chem. Lett., 16, 3479-3483.
    View publication on PubMed
Search for more literature for 1.1.1.205

Inhibitors

Inhibitors Comment Organism Structure
(2-[acetyl[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]amino]ethyl)phosphonic acid isozyme IMPDH II IC50: 785 nM Homo sapiens
(2-[formyl[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]amino]ethyl)phosphonic acid isozyme IMPDH II IC50: 749 nM Homo sapiens
(2-[[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](methyl)amino]ethyl)phosphonic acid isozyme IMPDH II IC50: above 0.001 mM Homo sapiens
(2-[[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](methylsulfonyl)amino]ethyl)phosphonic acid isozyme IMPDH II IC50: 498 nM Homo sapiens
(2-[[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](sulfamoyl)amino]ethyl)phosphonic acid isozyme IMPDH II IC50: 93 nM Homo sapiens
(2-[[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]amino]ethyl)phosphonic acid isozyme IMPDH II IC50: 499 nM Homo sapiens
(2-[[(2E)-4-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](methyl)amino]ethyl)phosphonic acid isozyme IMPDH II IC50: 132 nM Homo sapiens
(2-[[(2E)-4-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](methylsulfonyl)amino]ethyl)phosphonic acid isozyme IMPDH II IC50: 68 nM Homo sapiens
(2-[[(2E)-4-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](sulfamoyl)amino]ethyl)phosphonic acid isozyme IMPDH II IC50: 24 nM Homo sapiens
(2-[[(2E)-4-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]amino]ethyl)phosphonic acid isozyme IMPDH II IC50: 13 nM Homo sapiens
([[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]oxy]methyl)phosphonic acid isozyme IMPDH II IC50: 246 nM Homo sapiens
([[(2E)-4-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]oxy]methyl)phosphonic acid isozyme IMPDH II IC50: 23 nM Homo sapiens
7-hydroxy-5-methoxy-4-methyl-6-(3-methylbut-2-en-1-yl)-2-benzofuran-1(3H)-one isozyme IMPDH II IC50: 254 nM Homo sapiens
7-hydroxy-5-methoxy-6-[(2E)-4-methoxy-3-methylbut-2-en-1-yl]-4-methyl-2-benzofuran-1(3H)-one isozyme IMPDH II IC50: 273 nM Homo sapiens
dimethyl (2-[[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]amino]ethyl)phosphonate isozyme IMPDH II IC50: above 0.001 mM Homo sapiens
dimethyl [(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]phosphonate isozyme IMPDH II IC50: 289 nM Homo sapiens
additional information synthesis, inhibitory potency, and structure-activity relationship of enzyme with phosphonic acid-containing analogues of mycophenolic acid inhibitors, IC50 values, overview Homo sapiens
Mycophenolic acid isozyme IMPDH II IC50: 11 nM, potent, uncompetitive inhibition, immunosuppressive drug, prodrug is mycophenolate mofetil Homo sapiens
[(1E,3E)-5-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-3-methylpenta-1,3-dien-1-yl]phosphonic acid isozyme IMPDH II IC50: 506 nM Homo sapiens
[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]phosphonic acid isozyme IMPDH II IC50: 168 nM Homo sapiens
[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]phosphoramidic acid isozyme IMPDH II IC50: above 0.001 mM Homo sapiens
[(3E)-5-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-3-methylpent-3-en-1-yl]phosphonic acid isozyme IMPDH II IC50: 96 nM Homo sapiens
[(3E)-5-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-3-methylpent-3-en-1-yl]phosphonic acid isozyme IMPDH II IC50: 20 nM Homo sapiens
[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-en-1-yl]phosphonic acid isozyme IMPDH II IC50: 86 nM Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
inosine 5'-phosphate + NAD+ + H2O Homo sapiens rate-limiting step of the de novo guanine nucleotide biosynthesis xanthosine 5'-phosphate + NADH
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
 type I and type II isozymes
-

Source Tissue

Source Tissue Comment Organism Textmining
lymphocyte
-
 Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
inosine 5'-phosphate + NAD+ + H2O
-
 Homo sapiens xanthosine 5'-phosphate + NADH
-
 ?
inosine 5'-phosphate + NAD+ + H2O rate-limiting step of the de novo guanine nucleotide biosynthesis Homo sapiens xanthosine 5'-phosphate + NADH
-
 ?

Synonyms

Synonyms Comment Organism
IMPDH
-
 Homo sapiens
inosine monophosphate dehydrogenase
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Homo sapiens

Cofactor

Cofactor Comment Organism Structure
NAD+
-
 Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000011
-
 isozyme IMPDH II IC50: 11 nM, potent, uncompetitive inhibition, immunosuppressive drug, prodrug is mycophenolate mofetil Homo sapiens Mycophenolic acid
0.000013
-
 isozyme IMPDH II IC50: 13 nM Homo sapiens (2-[[(2E)-4-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]amino]ethyl)phosphonic acid
0.00002
-
 isozyme IMPDH II IC50: 20 nM Homo sapiens [(3E)-5-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-3-methylpent-3-en-1-yl]phosphonic acid
0.000023
-
 isozyme IMPDH II IC50: 23 nM Homo sapiens ([[(2E)-4-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]oxy]methyl)phosphonic acid
0.000024
-
 isozyme IMPDH II IC50: 24 nM Homo sapiens (2-[[(2E)-4-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](sulfamoyl)amino]ethyl)phosphonic acid
0.000068
-
 isozyme IMPDH II IC50: 68 nM Homo sapiens (2-[[(2E)-4-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](methylsulfonyl)amino]ethyl)phosphonic acid
0.000086
-
 isozyme IMPDH II IC50: 86 nM Homo sapiens [(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-en-1-yl]phosphonic acid
0.000093
-
 isozyme IMPDH II IC50: 93 nM Homo sapiens (2-[[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](sulfamoyl)amino]ethyl)phosphonic acid
0.000096
-
 isozyme IMPDH II IC50: 96 nM Homo sapiens [(3E)-5-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-3-methylpent-3-en-1-yl]phosphonic acid
0.000132
-
 isozyme IMPDH II IC50: 132 nM Homo sapiens (2-[[(2E)-4-(6-ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](methyl)amino]ethyl)phosphonic acid
0.000168
-
 isozyme IMPDH II IC50: 168 nM Homo sapiens [(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]phosphonic acid
0.000246
-
 isozyme IMPDH II IC50: 246 nM Homo sapiens ([[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]oxy]methyl)phosphonic acid
0.000254
-
 isozyme IMPDH II IC50: 254 nM Homo sapiens 7-hydroxy-5-methoxy-4-methyl-6-(3-methylbut-2-en-1-yl)-2-benzofuran-1(3H)-one
0.000273
-
 isozyme IMPDH II IC50: 273 nM Homo sapiens 7-hydroxy-5-methoxy-6-[(2E)-4-methoxy-3-methylbut-2-en-1-yl]-4-methyl-2-benzofuran-1(3H)-one
0.000289
-
 isozyme IMPDH II IC50: 289 nM Homo sapiens dimethyl [(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]phosphonate
0.000498
-
 isozyme IMPDH II IC50: 498 nM Homo sapiens (2-[[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](methylsulfonyl)amino]ethyl)phosphonic acid
0.000499
-
 isozyme IMPDH II IC50: 499 nM Homo sapiens (2-[[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]amino]ethyl)phosphonic acid
0.000506
-
 isozyme IMPDH II IC50: 506 nM Homo sapiens [(1E,3E)-5-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-3-methylpenta-1,3-dien-1-yl]phosphonic acid
0.000749
-
 isozyme IMPDH II IC50: 749 nM Homo sapiens (2-[formyl[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]amino]ethyl)phosphonic acid
0.000785
-
 isozyme IMPDH II IC50: 785 nM Homo sapiens (2-[acetyl[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]amino]ethyl)phosphonic acid
0.001
-
 isozyme IMPDH II IC50: above 0.001 mM Homo sapiens [(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]phosphoramidic acid
0.001
-
 isozyme IMPDH II IC50: above 0.001 mM Homo sapiens dimethyl (2-[[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]amino]ethyl)phosphonate
0.001
-
 isozyme IMPDH II IC50: above 0.001 mM Homo sapiens (2-[[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl](methyl)amino]ethyl)phosphonic acid