1.1.1.205: IMP dehydrogenase

This is an abbreviated version, for detailed information about IMP dehydrogenase, go to the full flat file.

Reaction

IMP
+
NAD+
+
H2O
=
XMP
+
NADH
+
H+

Synonyms

dehydrogenase, inosinate, EC 1.2.1.14, guaB2, IMD2, IMD3, IMD4, IMP dehydrogenase, IMP DH, IMP oxidoreductase, IMP-DH, IMP:NAD oxidoreductase, IMP:NAD+ oxidoreductase, IMPD, IMPDH, IMPDH II, IMPDH-1, IMPDH-B, IMPDH-S, IMPDH1, IMPDH2, inosinate dehydrogenase, inosine 5' monophosphate dehydrogenase, inosine 5'-monophosphate dehydrogenase, inosine 5'-monophosphate dehydrogenase 2, inosine 5'-phosphate dehydrogenase, inosine 5-monophosphate dehydrogenase, inosine 5-monophosphate dehydrogenase type I, inosine 5’ -monophosphate dehydrogenase, inosine monophosphate dehydrogenase, inosine monophosphate oxidoreductase, inosine-5'-monophosphate dehydrogenase, inosine-5'-phosphate dehydrogenase, inosinic acid 5’-monophosphate dehydrogenase, inosinic acid dehydrogenase, mpaF, Raspberry protein, SOI12, Superoxide-inducible protein 12, type 1 inosine monophosphate, type 2 inosine monophosphate dehydrogenase

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.205 IMP dehydrogenase

Inhibitors

Inhibitors on EC 1.1.1.205 - IMP dehydrogenase

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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(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
(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
(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
(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
(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
(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
(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
(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
(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
(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
(2E)-3-furan-2-yl-N-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]prop-2-enamide
(2E)-3-furan-2-yl-N-[4-(4-methyl-1,3-oxazol-5-yl)phenyl]prop-2-enamide
-
isozyme IMPDH II IC50: 0.002 mM
(2S)-2-[(1-naphthyl)amino]-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
competitive versus NAD+
(2S)-2-[(3,4-dichlorophenyl)amino]-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
competitive versus NAD+, displays excellent IMPDH inhibitory activity and moderate stability in mouse liver microsomes
(4E)-6-(4,6-dihydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
derivative of mycophenolic acid. IC50 value for K562 cells proliferation 8.2 microM; derivative of mycophenolic acid. IC50 value for K562 cells proliferation 8.2 microM
(4E)-6-[4-(acetyloxy)-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-4-methylhex-4-enoic acid
derivative of mycophenolic acid. IC50 value for K562 cells proliferation 0.59 microM; derivative of mycophenolic acid. IC50 value for K562 cells proliferation 0.59 microM
(4E)-N-hydroxy-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enamide
derivative of mycophenolic acid. IC50 value for K562 cells proliferation 2.1 microM; derivative of mycophenolic acid. IC50 value for K562 cells proliferation 2.1 microM
(5E)-N-hydroxy-7-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-5-methylhept-5-enamide
-
comparison with inhibition of histone deacetylase and K562 cell proliferation
([[(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
([[(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
1,4-dimethyl-6-nitro-2H-cyclopenta[d]pyridazine
-
;
1-(2,2-dimethylpropanoyl)-7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-1'H-spiro[pyrrolidine-3,2'-quinazolin]-4'(3'H)-one
-
IC50: 0.094 mM, isozyme IMPDH II
1-(2-[3-[(1E)-N-hydroxyethanimidoyl]phenyl]propan-2-yl)-3-quinolin-7-ylurea
-
displays high potency against Cryptosporidium parvum IMPDH, more than 1000fold selectivity versus human IMPDH type 2 and good stability in mouse liver microsomes
1-(3-methylphenyl)-3-[4-(1,3-oxazol-5-yl)phenyl]urea
-
isozyme IMPDH II IC50: 640 nM
1-(4-chloro-5-nitrocyclohexa-1,5-dien-1-yl)-3-(2-[3-[(1E)-N-hydroxyethanimidoyl]phenyl]propan-2-yl)urea
-
displays high potency against Cryptosporidium parvum IMPDH, more than 1000fold selectivity versus human IMPDH type 2 and good stability in mouse liver microsomes
1-(benzyloxy)-3-(3-pyridin-4-yl-1H-indol-6-yl)urea
-
;
1-methyl-6-[(5-phenyl-1,3-oxazol-2-yl)amino]-1H-indole-3-carbonitrile
-
;
1-phenylsulfonylindol-3-yl boronic acid
-
-
1-tert-butyl 5-methyl (3R,5R)-7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1,5-dicarboxylate
-
IC50: 35 nM, isozyme IMPDH II
1-tert-butyl 5-methyl (3R,5S)-7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1,5-dicarboxylate
-
IC50: 948 nM, isozyme IMPDH II
1-tert-butyl 5-methyl (3S,5R)-7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1,5-dicarboxylate
-
IC50: 35 nM, isozyme IMPDH II
1-tert-butyl 5-methyl (3S,5S)-7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1,5-dicarboxylate
-
26% inhibition at 10 micromol, isozyme IMPDH II
1-[2-[3-(prop-1-en-2-yl)phenyl]propan-2-yl]-3-quinolin-7-ylurea
-
displays high potency against Cryptosporidium parvum IMPDH, more than 1000fold selectivity versus human IMPDH type 2 and good stability in mouse liver microsomes
1-[3-chloro-4-(1,3-oxazol-5-yl)phenyl]-3-(3-methylphenyl)urea
-
isozyme IMPDH II IC50: 43 nM
1-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]-3-(3-methylphenyl)urea
-
isozyme IMPDH II IC50: 19 nM
1-[4-(4-methyl-1,3-oxazol-5-yl)phenyl]-3-(3-methylphenyl)urea
-
isozyme IMPDH II IC50: 500 nM
14,16-dihydroxy-3,8-dimethyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione
inhibition of leukemia K562 cells proliferation, IC50 of 71.3 microM
1H-naphtho[2,3-d]imidazol-2-ylmethyl 4-aminobenzoate
2'-deoxy-ATP
-
18% inhibition at 0.5 mM
2'-deoxy-GDP
-
12% inhibition at 0.5 mM
2'-deoxy-GTP
-
21% inhibition at 0.5 mM
2'-methylthiazole-4-carboxamide adenine dinucleotide
-
noncompetitive inhibition, less cytotoxic against K562 tumor cells
2-(1,3-oxazol-5-yl)-5-[(5-phenyl-1,3-oxazol-2-yl)amino]phenol
-
isozyme IMPDH II IC50: 0.0016 mM
2-(1-benzothiophen-3-yl)-6-methoxy-5-(1,3-oxazol-5-yl)-1H-indole-3-carbaldehyde
-
;
2-(dimethylamino)-7-methoxy-6-(1,3-oxazol-5-yl)quinolin-4(1H)-one
-
isozyme IMPDH II IC50: 200 nM
2-amino-oxazole-cyanoindoles
-
-
-
2-benzyl-7-methoxy-6-(1,3-oxazol-5-yl)quinolin-4(1H)-one
-
isozyme IMPDH II IC50: 180 nM
2-beta-D-ribofuranosylthiazole-4-carboxamide
-
NSC 286193, RTC
2-beta-D-ribofuranosylthiazole-4-carboxamide 5'-phosphate
-
RTC monophosphate
2-cyano-1-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]-3-phenylguanidine
-
isozyme IMPDH II IC50: 240 nM
2-ethyl-9-[5-O-[hydroxy(2-[hydroxy[2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethoxy]phosphoryl]ethyl)phosphoryl]-beta-L-ribofuranosyl]-9H-purin-6-amine
inhibition of leukemia K562 cells proliferation, IC50 of 4.0 microM; inhibition of leukemia K562 cells proliferation, IC50 of 4.0 microM
2-furan-3-yl-7-methoxy-6-(1,3-oxazol-5-yl)quinolin-4(1H)-one
-
isozyme IMPDH II IC50: 32 nM
2-hydroxy-N-[2-(2-[[3-methoxy-4-(1,3-oxazol-4-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-N-methylacetamide
-
isozyme IMPDH II IC50: 41 nM
2-mercaptoethanol
-
inhibits above 2 mM
2-methyl-3-(pyrid-4-yl)indole
-
IC50: 343 nM
2-tert-butyl-7-methoxy-6-(1,3-oxazol-5-yl)quinolin-4(1H)-one
-
isozyme IMPDH II IC50: 0.01 mM
2-[(3,4-dichlorophenyl)amino]-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
racemic variant, competitive versus NAD+. Compound displays good antiparasitic activity in a Toxoplasma gondii strain that relies on Cryptosporidium parvum IMPDH, EC50 20 nM. No toxicity is observed against four mammalian cells lines
2-[(3-ethyl-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl)sulfanyl]-N-(4-methoxyphenyl)acetamide
2-[2-(Z)-fluorovinyl]-inosine 5'-phosphate
-
is a time-dependent inactivator
2-[methyl[2-(2-[[3-(1,3-oxazol-5-yl)-1H-indol-6-yl]amino]-1,3-oxazol-5-yl)phenyl]amino]-2-oxoethyl acetate
-
;
2264A
-
inhibits lymphocyte proliferation; inhibits lymphocyte proliferation
2264B
-
inhibits lymphocyte proliferation; inhibits lymphocyte proliferation
3'-methylthiazole-4-carboxamide adenine dinucleotide
-
noncompetitive inhibition, less cytotoxic against K562 tumor cells
3-(1H-naphtho[2,3-d]imidazol-2-yl)propyl 4-aminobenzoate
3-(pyrid-4-yl)indole
-
-
3-carbamoylindole
-
-
3-cyanoindole
-
inhibits isozyme IMPDH II at 0.03 mM
3-cyanoindole-based inhibitors
-
synthesis and initial structure–activity relationships of 3-cyanoindole-based inhibitors with isozyme IMPDH II, IC50: 33-420 nM, comparison to other inhibitor structural classes, overview
-
3-formyl-1-methylindole
-
-
3-formylindole
-
-
3-hydrogenkwadaphnin
-
;
3-hydroxy-N-methyl-N-[2-(2-[[3-methyl-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]propanamide
-
isozyme IMPDH II IC50: 100 nM
3-hydroxy-N-[2-(2-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-N-methylpropanamide
-
isozyme IMPDH II IC50: 21 nM
3-methoxy-4-(oxazol-5-yl)aniline
-
-
3-phenyl quinolone derivatives
-
several, isozyme IMPDH II IC50: 5-160 nM, overview
-
4-pyridylindole
-
IC50: 0.00115 mM
4-[(1R)-1-[1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl]ethoxy]quinoline 1-oxide
4-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]amino]-6-phenyl-1,3,5-triazin-2-ol
-
;
5'-thio-IMP
-
competitive inhibitor
5,5'-dithiobis(2-nitrobenzoate)
-
-
5-bromoisoquinolin-6-amine
-
;
5-chloro-1,4-dimethyl-2H-cyclopenta[d]pyridazine-6-carbonitrile
-
;
6,6'-oxydi(1,4-dihydroquinoxaline-2,3-dione)
-
binds in the nicotinamide subsite and does not interact with ADP
6-((E)-4-(((1-(50-deoxy-adenosin-50-yl)-1H-1,2,3-triazol-4-yl)-methyl)amino)-3-methylbut-2-en-1-yl)-7-hydroxy-5-methoxy-4-methylisobenzofuran-1(3H)-one
;
6-((E)-4-(4-(adenosin-50-yl)methyl-1H-1,2,3-triazol-1-yl)-3-methylbut-2-en-1-yl)-7-hydroxy-5-methoxy-4-methylisobenzofuran-1(3H)-one
6-Chloro-9-beta-D-ribofuranosylpurine 5 '-phosphate
6-chloroinosine 5'-phosphate
6-Chloropurine
-
irreversible inhibitor
6-Chloropurine ribonucleoside 5'-phosphate
6-mercaptopurine ribonucleotide
-
-
6-thio-IMP
-
-
6-thioguanosine
-
expression of isoform IMPDH2 increases modestly in response to 6-thioguanosine exposure. However, the basal enzyme activity decreases when the cells are exposed to a proliferation-blocking 6-thioguanosine concentration
6-thioinosine 5'-phosphate
7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-1'H-spiro[cyclopentane-1,2'-quinazolin]-4'(3'H)-one
-
IC50: 328 nM, isozyme IMPDH II
7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-1-(piperidin-1-ylcarbonyl)-1'H-spiro[pyrrolidine-3,2'-quinazolin]-4'(3'H)-one
-
IC50: 0.068 mM, isozyme IMPDH II
7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-2,3,5,6-tetrahydro-1'H-spiro[pyran-4,2'-quinazolin]-4'(3'H)-one
-
IC50: 526 nM, isozyme IMPDH II
7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-N-phenyl-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1-carboxamide
-
IC50: 0.393 mM, isozyme IMPDH II
7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4,6-dihydro-1'H-spiro[cyclopenta[b]thiophene-5,2'-quinazolin]-4'(3'H)-one
-
IC50: 96 nM, isozyme IMPDH II
7'-methoxy-3'-methyl-N,N-bis(1-methylethyl)-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1-carboxamide
-
IC50: 0.071 mM, isozyme IMPDH II
7'-methoxy-N,3'-dimethyl-6'-(1,3-oxazol-5-yl)-4'-oxo-N-phenyl-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1-carboxamide
-
IC50: 0.064 mM, isozyme IMPDH II
7-hydroxy-5-methoxy-4-methyl-6-(3-methylbut-2-en-1-yl)-2-benzofuran-1(3H)-one
-
isozyme IMPDH II IC50: 254 nM
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
7-methoxy-2,2,3-trimethyl-6-(1,3-oxazol-5-yl)-2,3-dihydroquinazolin-4(1H)-one
-
IC50: 192 nM, isozyme IMPDH II
7-methoxy-2,2-dimethyl-6-(1,3-oxazol-5-yl)-3-(2-pyridin-4-ylethyl)-2,3-dihydroquinazolin-4(1H)-one
-
IC50: 300 nM, isozyme IMPDH II
7-methoxy-2,3-dimethyl-6-(1,3-oxazol-5-yl)-2-[(E)-2-phenylethenyl]-2,3-dihydroquinazolin-4(1H)-one
-
IC50: 49 nM, isozyme IMPDH II
7-methoxy-2-(3-methylphenyl)-6-(1,3-oxazol-5-yl)quinolin-4(1H)-one
-
;
7-methoxy-2-(methylamino)-6-(1,3-oxazol-5-yl)quinolin-4(1H)-one
-
isozyme IMPDH II IC50: 220 nM
7-methoxy-2-methyl-6-(1,3-oxazol-5-yl)quinolin-4(1H)-one
-
isozyme IMPDH II IC50: 110 nM
7-methoxy-3-methyl-6-(1,3-oxazol-5-yl)-2-phenylquinolin-4(1H)-one
-
isozyme IMPDH II IC50: 65 nM
7-methoxy-3-methyl-6-(1,3-oxazol-5-yl)quinazoline-2,4(1H,3H)-dione
-
IC50: 104 nM, isozyme IMPDH II
7-methoxy-6-(1,3-oxazol-4-yl)-2-phenylquinolin-4(1H)-one
-
isozyme IMPDH II IC50: 210 nM
7-methoxy-6-(1,3-oxazol-5-yl)-2-(1,3-thiazol-4-yl)quinolin-4(1H)-one
-
isozyme IMPDH II IC50: 34 nM
7-methoxy-6-(1,3-oxazol-5-yl)-2-phenoxyquinolin-4(1H)-one
-
isozyme IMPDH II IC50: 8 nM
7-methoxy-6-(1,3-oxazol-5-yl)-2-phenylquinolin-4(1H)-one
-
isozyme IMPDH II IC50: 8 nM
7-methoxy-6-(1,3-oxazol-5-yl)-2-pyridin-2-ylquinolin-4(1H)-one
-
isozyme IMPDH II IC50: 43 nM
7-methoxy-6-(1,3-oxazol-5-yl)-2-pyridin-3-ylquinolin-4(1H)-one
-
isozyme IMPDH II IC50: 70 nM
7-methoxy-6-(1,3-oxazol-5-yl)-2-pyridin-4-ylquinolin-4(1H)-one
-
isozyme IMPDH II IC50: 46 nM
7-methoxy-6-(1,3-oxazol-5-yl)-2-thiophen-2-ylquinolin-4(1H)-one
-
isozyme IMPDH II IC50: 63 nM
7-methoxy-6-(1,3-oxazol-5-yl)-2-thiophen-3-ylquinolin-4(1H)-one
-
isozyme IMPDH II IC50: 9 nM
7-methoxy-6-(1,3-oxazol-5-yl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
-
IC50: 303 nM
7-methoxy-6-(1,3-oxazol-5-yl)-3-(2-pyridin-4-ylethyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
-
;
7-methoxy-6-(1,3-oxazol-5-yl)quinolin-4(1H)-one
-
isozyme IMPDH II IC50: 300 nM
9-(5-deoxy-5-([(([2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethoxy]sulfonyl)methyl)sulfonyl]amino)-b-L-ribofuranosyl)-2-ethyl-9H-purin-6-amine
-
-
9-(5-deoxy-5-([(([2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethoxy]sulfonyl)methyl)sulfonyl]amino)-b-L-ribofuranosyl)-2-ethynyl-9H-purin-6-amine
-
-
9-(5-deoxy-5-([(([2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethoxy]sulfonyl)methyl)sulfonyl]amino)-b-L-ribofuranosyl)-2-phenyl-9H-purin-6-amine
-
-
9-(5-deoxy-5-([(([2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethoxy]sulfonyl)methyl)sulfonyl]amino)-b-L-ribofuranosyl)-9H-purin-6-amine
-
-
9-(5-O-[hydroxy[([hydroxy[2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethoxy]phosphoryl]oxy)methyl]phosphoryl]-beta-L-ribofuranosyl)-9H-purin-6-amine
allopurinol ribonucleotide
-
-
AVN944
-
induces caspase-independent apoptosis in multiple myeloma cell lines and displays antiproliferative activity against both androgen-dependent and androgen-independent prostate cancer cell lines; induces caspase-independent apoptosis in multiple myeloma cell lines and displays antiproliferative activity against both androgen-dependent and androgen-independent prostate cancer cell lines
benzamide riboside
beta-difluoromethylene-tiazofurin
-
;
beta-methylene thiazole 4-carboxamide adenine dinucleotide
beta-methylene-TAD
-
noncompetitive inhibition
beta-methylene-thiazole-4-carboxamide adenine dinucleotide
-
i.e. beta-Me-TAD, enzyme binding structure analysis, the enzyme active site loop is ordered in this complex, and the catalytic Cys319 is 3.6 A from IMP, in the same plane as the hypoxanthine ring, the active site loop forms hydrogen bonds to the carboxamide of beta-Me-TAD, overview
beta-methylene-thiazole-4-carboxyamide-adenine dinucleotide
-
-
beta-methylene-tiazofurin
-
;
blastadin 11
-
;
BMS-337197
C2-mycophenolic adenine dinucleotide
C4-mycophenolic adenine dinucleotide
-
methylenephosphophosphonate analogue of mycophenolic adenine dinucleotide
CH2-SAD
i.e. 4-carboxamido-2-beta-D-ribofuranosylselenazolyl adenosine methylenediphosphonic acid, an adenine dinucleotide analogue nonhydrolyzable beta-methylene derivative
CH2-TAD
i.e. 4-carboxamido-2-beta-D-ribofuranosylthiazolyl adenosine methylenediphosphonic acid, an adenine dinucleotide analogue nonhydrolyzable beta-methylene derivative
chlorogenic acid
0.1 mM, 30% inhibition
CMP
-
25% inhibition at 0.6 mM
curcumin
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
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
dithioerythrol
-
inhibits above 1 mM
EICARMP
eicosadienoic acid
ellagic acid
0.1 mM, 27% inhibition
epigallocatechin gallate
0.1 mM, 47% inhibition
ethyl 7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1-carboxylate
-
IC50: 0.08 mM, isozyme IMPDH II
ethyl 9-oxo-9,10-dihydroacridine-1-carboxylate
-
;
Fe3+
-
11% inhibition at 1 nM
FFAD
-
;
glutathione
-
above 4 mM
halicyclamine A
-
;
helenalin
-
;
HgCl2
-
complete inactivation at 0.5 mM
imidazo[4,5-e][1,4]diazapine
Inosine
-
very weak, non-competitive
Inosine 5'-methylphosphonate
-
very weak, non-competitive
inosine 5'-phosphate
-
Inosine 5'-phosphite
-
very weak, non-competitive
Inosine 5'-phosphofluoridate
-
very weak, non-competitive
iodoacetamide
-
-
iodoacetate
K+
-
above 0.1 M
linoleic acid
merimepodib
-
has immunosuppressive activity; has immunosuppressive activity
methyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate
derivative of mycophenolic acid. IC50 value for K562 cells proliferation 0.73 microM; derivative of mycophenolic acid. IC50 value for K562 cells proliferation 0.73 microM
methyl 3-methyl-2-oxo-1,2-dihydroquinoline-4-carboxylate
methyl methanethiosulfonate
-
-
mizobirine 5'-monophosphate
-
-
mizoribine
mizoribine 5'-monophosphate
-
mizoribine 5'-phosphate
mizoribine monophosphate
mycophenolate mofetil
mycophenolic 2-ethyladenosin-5'-yl-difluoromethylenebis(phosphonate)
potent, sub-micromolar inhibitor of leukemia K562 cells proliferation, IC50 of 0.45 microM; potent, sub-micromolar inhibitor of leukemia K562 cells proliferation, IC50 of 0.45 microM
mycophenolic 2-ethyladenosin-5'-yl-methylenebis(phosphonate)
inhibition of leukemia K562 cells proliferation, IC50 of 1.0 microM; inhibition of leukemia K562 cells proliferation, IC50 of 1.0 microM
Mycophenolic acid
mycophenolic acid glucuronide
-
80% inhibition at 0.2 mM, human plasma or serum reduces the inhibition
mycophenolic acid-acyl-glucuronide
mycophenolic adenine dinucleotide
-
-
mycophenolic hydroxamic acid
-
comparison with inhibition of histone deacetylase and K562 cell proliferation
N,7'-dimethoxy-N,3'-dimethyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1-carboxamide
-
IC50: 0.079 mM, isozyme IMPDH II
N,N-diethyl-7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1-carboxamide
-
IC50: 0.045 mM, isozyme IMPDH II
N-(2,3-dichlorophenyl)-2-[2-(1,3-thiazol-2-yl)-1H-benzimidazol-1-yl]acetamide
-
poor inhibition of human IMPDH2
N-(2,4-difluorophenyl)-7'-methoxy-N,3'-dimethyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1-carboxamide
-
IC50: 0.051 mM, isozyme IMPDH II
N-(4-bromophenyl)-2-[2-(1,3-thiazol-2-yl)-1H-benzimidazol-1-yl]acetamide
-
crystallization data. Poor inhibition of human IMPDH2
N-(4-chlorophenyl)-2-phenoxypropanamide
-
antagonizes ADP binding
N-(4-methoxyphenyl)-2-(3-methyl-4-oxo-3,4-dihydrophthalazin-1-yl)acetamide
N-(4-methoxyphenyl)-2-naphthalen-1-ylacetamide
-
binds in the nicotinamide subsite and does not interact with ADP
N-(4-methoxyphenyl)-2-[2-(1,3-thiazol-4-yl)-1H-benzimidazol-1-yl]acetamide
N-(5-phenyl-1,3-oxazol-2-yl)isoquinolin-6-amine
-
;
N-(naphthalen-2-yl)-2-[2-(1,3-thiazol-2-yl)-1H-benzimidazol-1-yl]acetamide
-
poor inhibition of human IMPDH2
N-(naphthalen-2-yl)-2-[2-(1,3-thiazol-4-yl)-1H-benzimidazol-1-yl]acetamide
-
poor inhibition of human IMPDH2
N-(naphthalen-2-yl)-2-[2-(pyridin-2-yl)-1H-benzimidazol-1-yl]acetamide
N-(naphthalen-2-yl)-2-[2-(pyridin-2-yl)-5,6-dihydro-1H-benzimidazol-1-yl]acetamide
N-ethyl-7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1-carboxamide
-
IC50: 0.119 mM, isozyme IMPDH II
N-ethylmaleimide
-
100% inhibition at 1 mM
N-hydroxy-N'-[3-methoxy-4-(1,3-oxazol-2-yl)phenyl]octanediamide
-
comparison with inhibition of histone deacetylase and K562 cell proliferation
N-methyl-N'-[4-(1,3-oxazol-5-yl)phenyl]-6-phenyl-1,3,5-triazine-2,4-diamine
-
isozyme IMPDH II IC50: 0.005 mM
N-methyl-N'-[4-(4-methyl-1,3-oxazol-5-yl)phenyl]-6-phenyl-1,3,5-triazine-2,4-diamine
-
isozyme IMPDH II IC50: 0.005 mM
N-methyl-N-[2-(2-[[3-methyl-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-3-morpholin-4-ylpropanamide
-
isozyme IMPDH II IC50: 45 nM
N-tert-butyl-N'-[3-chloro-4-(1,3-oxazol-5-yl)phenyl]ethanediamide
-
isozyme IMPDH II IC50: 55 nM
N-tert-butyl-N'-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]ethanediamide
-
isozyme IMPDH II IC50: 10 nM
N-tert-butyl-N'-[4-(1,3-oxazol-5-yl)phenyl]ethanediamide
-
isozyme IMPDH II IC50: 0.005 mM
N-tert-butyl-N'-[4-(4-methyl-1,3-oxazol-5-yl)phenyl]ethanediamide
-
isozyme IMPDH II IC50: 0.005 mM
N-[(Z)-(pyridin-3-ylimino)methyl]-2,3-dihydro-1,4-benzodioxine-2-carboxamide
-
-
N-[1-[6-(4-ethylpiperazin-1-yl)pyridin-3-yl]-1-methylethyl]-2-fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide
-
;
N-[2-(2-[[3-(chloromethyl)-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-N-methyl-3-morpholin-4-ylpropanamide
-
isozyme IMPDH II IC50: 47 nM
N-[2-(2-[[3-bromo-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-3-hydroxy-N-methylpropanamide
-
isozyme IMPDH II IC50: 28 nM
N-[2-(2-[[3-bromo-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-N-methyl-3-morpholin-4-ylpropanamide
-
isozyme IMPDH II IC50: 21 nM
N-[2-(2-[[3-chloro-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-3-hydroxy-N-methylpropanamide
-
isozyme IMPDH II IC50: 48 nM
N-[2-(2-[[3-ethyl-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-3-hydroxy-N-methylpropanamide
-
isozyme IMPDH II IC50: 310 nM
N-[2-(2-[[3-ethyl-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-N-methyl-3-morpholin-4-ylpropanamide
-
isozyme IMPDH II IC50: 21 nM
N-[2-(2-[[3-methoxy-4-(1,3-oxazol-4-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-N-methyl-2-morpholin-4-ylacetamide
-
isozyme IMPDH II IC50: 91 nM
N-[2-(2-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-N-methyl-2-morpholin-4-ylacetamide
-
;
N-[2-(2-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]amino]-1,3-oxazol-5-yl)phenyl]-N-methyl-3-morpholin-4-ylpropanamide
-
isozyme IMPDH II IC50: 16 nM
N-[2-(hydroxymethyl)cyclopentyl]-N'-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]propanediamide
-
;
N-[2-chloro-3-methoxy-4-(1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.005 mM
N-[2-chloro-5-methoxy-4-(1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.0016 mM
N-[2-fluoro-5-methoxy-4-(1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.005 mM
N-[3-bromo-4-(1,3-oxazol-5-yl)phenyl]-N'-tert-butylethanediamide
-
isozyme IMPDH II IC50: 50 nM
N-[3-chloro-4-(1,3-oxazol-4-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.005 mM
N-[3-chloro-4-(1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 88 nM
N-[3-chloro-4-(1,3-oxazol-5-yl)phenyl]-N'-methyl-6-phenyl-1,3,5-triazine-2,4-diamine
-
isozyme IMPDH II IC50: 340 nM
N-[3-ethoxy-4-(1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.010 mM
N-[3-methoxy-4-(1,3-oxazol-2-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 190 nM
N-[3-methoxy-4-(1,3-oxazol-4-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 57 nM
N-[3-methoxy-4-(1,3-oxazol-4-yl)phenyl]-N'-methyl-6-phenyl-1,3,5-triazine-2,4-diamine
-
isozyme IMPDH II IC50: 0.0016 mM
N-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 20 nM
N-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]-N'-methyl-6-phenyl-1,3,5-triazine-2,4-diamine
-
isozyme IMPDH II IC50: 76 nM
N-[3-methoxy-4-(1H-1,2,4-triazol-1-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 410 nM
N-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.002 mM
N-[3-methoxy-4-(4-methyl-1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.005 mM
N-[3-methyl-4-(1,3-oxazol-4-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.005 mM
N-[4-(1,3-oxazol-4-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.005 mM
N-[4-(1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.005 mM
N-[4-(2,4-dimethyl-1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.002 mM
N-[4-(4-methyl-1,3-oxazol-5-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine
-
isozyme IMPDH II IC50: 0.005 mM
N-[4-chloro-3-(trifluoromethyl)phenyl]-2-(3-methyl-4-oxo-3,4-dihydrophthalazin-1-yl)acetamide
-
noncompetitive with respect to NAD+, displays submicromolar activity in a Toxoplasma gondii model of Cryptosporidium parvum infection and displays good stability in mouse liver microsome. No antiparasitic activity is observed in mouse with once per day oral dosing of 250 mg/kg for 7 days
NADPH
-
50% inhibition at 0.14 mM
NH4+
-
25% inhibition at 2.12 M
nicotinic acid
-
inhibitory analog of NAD+, non-competitive with respect to IMP and K+
p-chloromercuribenzoate
p-hydroxymercuribenzoate
-
97% inactivation at 1 mM
P1-(7-hydroxy-6-(ethyl-2-yl)-5-methoxy-4-methylphthalan-1-one)methylenephospho-P2-(adenosin-5'-yl)phosphonate
-
-
P1-(adenosine-5'-yl)methylenephospho-P2-(7-hydroxy-6-(ethyl-2-yl)-5-methoxy-4-methylphthalan-1-one)phosphonate
-
-
P1-(thiazofurin-5'-yl)-P2-(adenosyl-5'-yl)-alpha,beta-methylene diphosphate
P1-(tiazofurin-5'-yl)-P2-(2-aminoadenosin-5'-yl) diphosphate
-
comparison with inhibition of alcohol dehydrogenase, malate dehydrogenase, lactate dehydrogenase and K562 cell proliferation
P1-(tiazofurin-5'-yl)-P2-(2-ethyladenosin-5'-yl) diphosphate
-
comparison with inhibition of alcohol dehydrogenase, malate dehydrogenase, lactate dehydrogenase and K562 cell proliferation
P1-(tiazofurin-5'-yl)-P2-(2-ethynyladenosin-5'-yl) diphosphate
-
comparison with inhibition of alcohol dehydrogenase, malate dehydrogenase, lactate dehydrogenase and K562 cell proliferation
P1-(tiazofurin-5'-yl)-P2-(2-iodoadenosin-5'-yl) diphosphate
-
comparison with inhibition of alcohol dehydrogenase, malate dehydrogenase, lactate dehydrogenase and K562 cell proliferation
P1-(tiazofurin-5'-yl)-P2-(2-phenyladenosin-5'-yl) diphosphate
-
comparison with inhibition of alcohol dehydrogenase, malate dehydrogenase, lactate dehydrogenase and K562 cell proliferation
P1-(tiazofurin-5'-yl)-P2-(adenosin-5'-yl) diphosphate
-
comparison with inhibition of alcohol dehydrogenase, malate dehydrogenase, lactate dehydrogenase and K562 cell proliferation
P1-[7-hydroxy-6-(hydroxyethyl)-5-methoxy-4-methylphthtalan-1-one-2-yl]-P2-(2-ethyladenosin-5'-yl)methylenebis(phosphonate)
-
-
P1-[7-hydroxy-6-(hydroxyethyl)-5-methoxy-4-methylphthtalan-1-one-2-yl]-P2-(2-phenyladenosin-5'-yl)methylenebis(phosphonate)
-
-
P1-[7-hydroxy-6-(hydroxyethyl)-5-methoxy-4-methylphthtalan-1-one-2-yl]-P2-(adenosin-5'-yl)methylenebis(phosphonate)
-
-
pellynic acid
-
;
phenyl N'-cyano-N-(3-[cyano[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamimidamido]benzyl)imidocarbamate
-
;
phosphate
-
mixed inhibition kinetics
quinazolinedione derivatives
-
several derivatives, synthesis and inhibitory values, overview
-
quinazolinethione derivatives
-
several derivatives, synthesis and inhibitory values, overview
-
ribavirin
ribavirin 5'-monophosphate
ribavirin 5'-phosphate
ribavirin monophosphate
ribose 5-phosphate
-
non-competitive
SAD
i.e. selenazole-4-carboxamido adenine diphosphonic acid, an adenine dinucleotide analogue
Selenazofurin
selenazole adenine dinucleotide
-
-
selenazole-4-carboxyamide-adenine dinucleotide
-
;
Sesquiterpene lactones
-
a class of anti-neoplastic drugs, overview
-
SFAD
-
;
TAD
i.e. thiazole-4-carboxamide adenine dinucleotide, an adenine dinucleotide analogue
tert-butyl 7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1H,1'H-spiro[pyrrolidine-3,2'-quinazoline]-1-carboxylate
-
IC50: 104 nM, isozyme IMPDH II
tert-butyl methyl (1S,4S)-7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1'H-spiro[cyclopentane-1,2'-quinazoline]-3,4-dicarboxylate
-
;
TFAD
-
;
thiazofurin-5'-yl-2-ethyladenosin-5'-yl-difluromethylene bis(phosphonate)
inhibition of leukemia K562 cells proliferation, IC50 of 4.7 microM; inhibition of leukemia K562 cells proliferation, IC50 of 4.7 microM
thiazole-4-carboxamide 2-ethyladenine dinucleotide
;
thiazole-4-carboxamide adenine dinucleotide
tiazofurin
TMP
-
25% inhibition at 0.6 mM
UMP
-
25% inhibition at 0.6 mM
Urea
-
inactive at 3 M but regains activity after dialysis
VX-148
VX-497
xanthosine 5'-phosphate
Zn2+
-
complete inhibition at 1 nM
[(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
[(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
[(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
[(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
[(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
[(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
additional information
-