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Literature summary for 1.1.1.205 extracted from

  • Dunkern, T.; Chavan, S.; Bankar, D.; Patil, A.; Kulkarni, P.; Kharkar, P.S.; Prabhu, A.; Goebel, H.; Rolser, E.; Burckhard-Boer, W.; Arumugam, P.; Makhija, M.T.
    Design, synthesis and biological evaluation of novel inosine 5-monophosphate dehydrogenase (IMPDH) inhibitors (2014), J. Enzyme Inhib. Med. Chem., 29, 408-419.
    View publication on PubMed
Search for more literature for 1.1.1.205

Application

Application Comment Organism
drug development the inhibition of IMPDH (leading to reduced cellular levels of guanine nucleotides) is an important strategy for antiproliferative, antiviral and antiparasitic effects. It is also a useful strategy for producing immunosuppression as IMPDH-dependent de novo synthesis of guanine nucleotides is responsible for maintaining the growth and differentiation of human B and T lymphocytes Homo sapiens

Cloned(Commentary)

Cloned (Comment) Organism
gene IMPDH2, recombinant expression in Escherichia coli strain BL21(DE3), subcloning in Escherichia coli strain DH5alpha Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(2E)-3-{3-[N''-cyano-N'-(4-cyano-3-methoxyphenyl)carbamimidamido]phenyl}prop-2-enoic acid
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(2,3-dihydro-1-benzofuran-7-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(2-acetyl-1-methyl-2,3-dihydro-1H-benzimidazol-4-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(2-methoxyquinoxalin-5-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(2H-1,3-benzodioxol-5-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(3,4-dimethoxybenzene-1-sulfonyl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(3-methoxy-4-methylphenyl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(3-methoxyquinoxalin-5-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(4-cyano-3-methoxyphenyl)carbamoyl]amino}phenyl)ethyl]carbamate i.e. VX-4997 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(4-methyl-2,3-dihydro-1-benzofuran-6-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(5,6-dihydro-1,4-dioxin-2-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(6,7-dimethoxynaphthalen-1-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(E)-1-(3,4-dimethoxyanilino)-2-nitroethenyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(E)-1-(4-cyano-3-methoxyanilino)-2-nitroethenyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[4-(4-cyano-3-methoxyphenyl)piperazine-1-carbonyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[5-(4-cyano-3-methoxyphenyl)-1H-benzimidazol-2-yl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[6-(4-cyano-3-methoxyphenyl)pyrazine-2-carbonyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-{3-[2-(3,4-dimethoxyphenoxy)acetamido]phenyl}ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-{3-[2-(4-cyano-3-methoxyphenoxy)acetamido]phenyl}ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-{3-[3-(4-cyano-3-methoxyphenyl)-2,4-dioxoimidazolidin-1-yl]phenyl}ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl [(1S)-1-{3-[N'-(3,4-dimethoxyphenyl)carbamimidamido]phenyl}ethyl]carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl {(1S)-1-[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]ethyl}carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl {(1S)-1-[3-({[3-methoxy-4-(morpholin-4-yl)phenyl]carbamoyl}amino)phenyl]ethyl}carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl {(1S)-1-[3-({[3-methoxy-4-(oxan-4-yl)phenyl]carbamoyl}amino)phenyl]ethyl}carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl {(1S)-1-[3-({[4-(3,6-dihydro-2H-pyran-4-yl)-3-methoxyphenyl]carbamoyl}amino)phenyl]ethyl}carbamate
-
 Homo sapiens
(2R)-1-cyanobutan-2-yl-[(1S)-1-(3-{[(3,4-dimethoxyphenyl)carbamoyl]amino}phenyl)-ethyl] carbamate
-
 Homo sapiens
(2S)-1-cyanobutan-2-yl [(1R)-1-(3-{[(3,4-dimethoxyphenyl)carbamothioyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2S)-1-cyanobutan-2-yl [(1R)-1-(3-{[(4-cyano-3-methoxyphenyl)carbamothioyl]amino}phenyl)ethyl]carbamate
-
 Homo sapiens
(2S)-1-cyanobutan-2-yl [(1R)-1-{3-[N''-cyano-N'-(4-cyano-3,5-dimethoxyphenyl)carbamimidamido]phenyl}ethyl]carbamate
-
 Homo sapiens
(2S)-1-cyanobutan-2-yl [(1R)-1-{3-[N'-(3,4,5-trimethoxyphenyl)carbamimidamido]phenyl}ethyl]carbamate
-
 Homo sapiens
(2S)-1-cyanobutan-2-yl [(1R)-1-{3-[N'-(4-cyano-3,5-dimethoxyphenyl)carbamimidamido]phenyl}ethyl]carbamate
-
 Homo sapiens
(3S)-oxolan-3-yl {[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]methyl}carbamate i.e. VX-148, structure-activity relationship analysis, overview Homo sapiens
2-(1-benzothiophen-3-yl)-6-methoxy-5-(1,3-oxazol-2-yl)-1H-indole-3-carbaldehyde
-
 Homo sapiens
3'-[N''-cyano-N'-(4-cyano-3-methoxyphenyl)carbamimidamido][1,1'-biphenyl]-3-carboxylic acid
-
 Homo sapiens
3-(2-{2-[3-methoxy-4-(1,3-oxazol-5-yl)anilino]-1,3-oxazol-5-yl}phenyl)-1-(morpholin-4-yl)butan-2-one i.e. BMS-337197 Homo sapiens
3-{3-[N''-cyano-N'-(4-cyano-3-methoxyphenyl)carbamimidamido]phenyl}propanoic acid
-
 Homo sapiens
4-isothiocyanato-1,2-dimethoxybenzene
-
 Homo sapiens
4-isothiocyanato-2-methoxybenzonitrile
-
 Homo sapiens
7-methoxy-6-(1,3-oxazol-2-yl)-2-phenylquinolin-4(1H)-one
-
 Homo sapiens
7-methoxy-6-(1,3-oxazol-5-yl)-3-[2-(pyridin-4-yl)ethyl]-2-sulfanylidene-2,3-dihydroquinazolin-4(1H)-one
-
 Homo sapiens
GMP
-
 Homo sapiens
additional information structure- and ligand-based IMPDH inhibitor development, molecular modeling studies, overview Homo sapiens
Mycophenolic acid a natural product and a reversible, potent and uncompetitive inhibitor of IMPDH Homo sapiens
N''-cyano-N-(3'-cyano[1,1'-biphenyl]-3-yl)-N'-(4-cyano-3-methoxyphenyl)guanidine
-
 Homo sapiens
N''-cyano-N-(4'-cyano[1,1'-biphenyl]-3-yl)-N'-(4-cyano-3-methoxyphenyl)guanidine
-
 Homo sapiens
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-(2'-fluoro[1,1'-biphenyl]-3-yl)guanidine
-
 Homo sapiens
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-(3'-fluoro[1,1'-biphenyl]-3-yl)guanidine
-
 Homo sapiens
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-(4'-fluoro[1,1'-biphenyl]-3-yl)guanidine
-
 Homo sapiens
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-[3'-(trifluoromethyl)[1,1'-biphenyl]-3-yl]guanidine
-
 Homo sapiens
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-[3-(1-hydroxyethenyl)phenyl]guanidine
-
 Homo sapiens
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-[3-(2-hydroxyprop-2-en-1-yl)phenyl]guanidine
-
 Homo sapiens
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-[3-(2-methyl-2H-tetrazol-5-yl)phenyl]guanidine
-
 Homo sapiens
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-{3-[(1-methyl-1H-tetrazol-5-yl)methyl]phenyl}guanidine
-
 Homo sapiens
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-{3-[(2-methyl-2H-tetrazol-5-yl)methyl]phenyl}guanidine
-
 Homo sapiens
N-{2-[6-(4-ethylpiperazin-1-yl)pyridin-3-yl]propan-2-yl}-2-fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide
-
 Homo sapiens
propan-2-yl {3-[N''-cyano-N'-(4-cyano-3-methoxyphenyl)carbamimidamido]phenoxy}acetate
-
 Homo sapiens
{3-[N''-cyano-N'-(4-cyano-3-methoxyphenyl)carbamimidamido]phenoxy}acetic acid
-
 Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
IMP + NAD+ Homo sapiens
-
 XMP + NADH + H+
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens P12268
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
IMP + NAD+
-
 Homo sapiens XMP + NADH + H+
-
 ?

Synonyms

Synonyms Comment Organism
IMPDH
-
 Homo sapiens
IMPDH II
-
 Homo sapiens
IMPDH2
-
 Homo sapiens
inosine 5-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

General Information

General Information Comment Organism
physiological function the enzyme catalyzes a crucial step in the de novo synthesis of guanine nucleotides. It oxidizes inosine 5'-monophosphate (IMP) to xanthosine 5'-monophosphate (XMP) in a nicotinamide adenine dinucleotide (NAD+)-dependent manner. The enzyme has a critical position in the purine biosynthesis pathway Homo sapiens