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Information on EC 1.1.1.205 - IMP dehydrogenase
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1.1.1.205 IMP dehydrogenaseIUBMB Comments
The enzyme acts on the hydroxy group of the hydrated derivative of the substrate.
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Word Map
- 1.1.1.205
-
mycophenolic
- guanine
- purine
- mofetil
- ribavirin
- leukemia
- tiazofurin
-
rejection
-
salvage
-
cyclosporine
- xmp
-
pharmacodynamic
- hypoxanthine
- mizoribine
-
guanylate
- ribonucleotide
-
prodrugs
- xanthosine
- phosphoribosyltransferase
-
allograft
- adenylosuccinate
- tad
- benzamide
- pigmentosa
- azathioprine
- riboside
- dgtp
- thiopurine
- 6-mercaptopurine
- cryptosporidium
- glucuronide
- calcineurin
-
hypoxanthine-guanine
- tacrolimus
- parvum
- dihydrofolate
- 6-thioguanine
-
amido
- sirolimus
-
interpatient
-
enteric-coated
- pharmacology
- medicine
-
c-nucleoside
- drug development
- diagnostics
- analysis
-
predose
- hgprt
- rbv
- tritrichomonas
The enzyme appears in viruses and cellular organisms
Synonyms
impdh, imp dehydrogenase, inosine monophosphate dehydrogenase, impdh2, impdh1, inosine 5'-monophosphate dehydrogenase, inosine-5'-monophosphate dehydrogenase, impdh ii, imp dh, inosinate dehydrogenase, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
class I IMPDH
class II IMPDH
guaB
guaB2
IMP dehydrogenase
IMP DH
IMP oxidoreductase
IMPDH
IMPDH II
IMPDH2
IMPDHab
IMPDHkp
IMPDHlpp
inosinate dehydrogenase
inosine 5' monophosphate dehydrogenase
inosine 5'-monophosphate dehydrogenase
inosine 5'-phosphate dehydrogenase
-
-
inosine 5-monophosphate dehydrogenase
inosine 5’-monophosphate dehydrogenase 2
inosine monophosphate dehydrogenase
inosine monophosphate oxidoreductase
inosine-5'-monophosphate dehydrogenase
lpg1723
Rv3411c
IMPDH
-
-
inosine monophosphate dehydrogenase
-
-
inosine-5'-monophosphate dehydrogenase
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
IMP + NAD+ + H2O = XMP + NADH + H+
enzyme acts on the hydroxyl group of the hydrated derivative of the substrate, ordered bi-bi mechanism
-
IMP + NAD+ + H2O = XMP + NADH + H+
enzyme acts on the hydroxyl group of the hydrated derivative of the substrate, ordered bi-bi mechanism
-
IMP + NAD+ + H2O = XMP + NADH + H+
IMP and K+ can bind randomly to the free enzyme, while NAD+ does not react unless K+ or both K+ and IMP are present on the enzyme
-
IMP + NAD+ + H2O = XMP + NADH + H+
IMP binds first, followed by NAD+, NADH dissociates from the ternary complex first, then XMP is released
-
IMP + NAD+ + H2O = XMP + NADH + H+
mechanism is partially random
-
IMP + NAD+ + H2O = XMP + NADH + H+
Arg418 is involved in the reaction mechanism as catalytic base
-
IMP + NAD+ + H2O = XMP + NADH + H+
covalent enzyme reaction intermediate, hydrolysis of enzyme-XMP is rate-limiting and requires the adoption of the closed conformation, Arg418 is involved in the reaction mechanism as catalytic base, Thr321 is involved in both hydride transfer and hydrolysis
-
IMP + NAD+ + H2O = XMP + NADH + H+
reaction and kinetic mechanism, an Arg residue is involved in catalysis as general base
-
IMP + NAD+ + H2O = XMP + NADH + H+
reaction and kinetic mechanism, an Arg residue is involved in catalysis as general base, Cys319-linked covalent enzyme intermediate E-XMP
-
IMP + NAD+ + H2O = XMP + NADH + H+
substrate binding and catalytic reaction mechanism, Cys319 is the catalytic residue, NAD+ promotes the nucleophilic attack of Cys319 on IMP
-
IMP + NAD+ + H2O = XMP + NADH + H+
a steady-state ordered Bi Bi kinetic mechanism in which IMP binds first followed by NAD+, and product release is ordered. Hydride transfer appears not to be rate-limiting. The pH-rate profile indicates one deprotonated group essential for catalysis
IMP + NAD+ + H2O = XMP + NADH + H+
reaction in two steps via covalent interemediate state, the catalytic residue is Cys334
IMP + NAD+ + H2O = XMP + NADH + H+
the enzymatic mechanism of IMPDH consists two steps, a dehydrogenase and a hydrolase reaction. Upon binding of IMP and NAD+ cofactor, a thioimidate enzyme-substrate adduct, E-XMP*, is formed via a covalent bond to the catalytic C341 with concurrent production of NADH. Hydride transfer occurs to the pro-S position with the cofactor in the anti-conformation. The cofactor is released and an active site mobile flap moves into the NAD+ site and facilitates E-XMP* hydrolysis with a conserved R443 acting as a general base. The enzyme has two distinct conformations, an open form for the dehydrogenase reaction and a closed form for E-XMP* hydrolysis
IMP + NAD+ + H2O = XMP + NADH + H+
the IMPDH reaction involves two chemical transformations. First, the catalytic Cys attacks IMP, and hydride is transferred to NAD to form the covalent intermediate E-XMP*. In the second step, E-XMP* is hydrolyzed to produce XMP
-
IMP + NAD+ + H2O = XMP + NADH + H+
the IMPDH reaction involves two chemical transformations. First, the catalytic Cys attacks IMP, and hydride is transferred to NAD to form the covalent intermediate E-XMP*. In the second step, E-XMP* is hydrolyzed to produce XMP
-
IMP + NAD+ + H2O = XMP + NADH + H+
the IMPDH reaction involves two chemical transformations. First, the catalytic Cys attacks IMP, and hydride is transferred to NAD to form the covalent intermediate E-XMP*. In the second step, E-XMP* is hydrolyzed to produce XMP
-
IMP + NAD+ + H2O = XMP + NADH + H+
the IMPDH reaction involves two chemical transformations. First, the catalytic Cys attacks IMP, and hydride is transferred to NAD to form the covalent intermediate E-XMP*. In the second step, E-XMP* is hydrolyzed to produce XMP
-
IMP + NAD+ + H2O = XMP + NADH + H+
the enzymatic mechanism of IMPDH consists two steps, a dehydrogenase and a hydrolase reaction. Upon binding of IMP and NAD+ cofactor, a thioimidate enzyme-substrate adduct, E-XMP*, is formed via a covalent bond to the catalytic C341 with concurrent production of NADH. Hydride transfer occurs to the pro-S position with the cofactor in the anti-conformation. The cofactor is released and an active site mobile flap moves into the NAD+ site and facilitates E-XMP* hydrolysis with a conserved R443 acting as a general base. The enzyme has two distinct conformations, an open form for the dehydrogenase reaction and a closed form for E-XMP* hydrolysis
-
IMP + NAD+ + H2O = XMP + NADH + H+
a steady-state ordered Bi Bi kinetic mechanism in which IMP binds first followed by NAD+, and product release is ordered. Hydride transfer appears not to be rate-limiting. The pH-rate profile indicates one deprotonated group essential for catalysis
-
IMP + NAD+ + H2O = XMP + NADH + H+
reaction in two steps via covalent interemediate state, the catalytic residue is Cys334
-
IMP + NAD+ + H2O = XMP + NADH + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
IMP:NAD+ oxidoreductase
The enzyme acts on the hydroxy group of the hydrated derivative of the substrate.
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CAS REGISTRY NUMBER
COMMENTARY
9028-93-7
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
5'-amino-5'-deoxyinosine 5'-N-phosphate + NAD+ + H2O
5'-amino-5'-deoxyxanthosine 5'-N-phosphate + NADH
-
-
-
?
5'-mercapto-5'-deoxyinosine 5'-S-phosphate + NAD+ + H2O
5'-mercapto-5'-deoxyxanthosine 5'-phosphate + NADH
-
-
-
?
6-thioinosine 5'-phosphate + NAD+ + H2O
6-thioxanthosine 5'-phosphate + NADH
-
-
-
?
IMP + thiazole-4-carboxamide adenine dinucleotide + H2O
XMP + reduced thiazole-4-carboxamide adenine dinucleotide + H+
-
-
-
r
inosine + NAD+ + H2O
xanthosine + NADH
-
8% of the rate with inosine 5'-phosphate
-
?
inosine 5'-diphosphate + NAD+ + H2O
xanthosine 5'-diphosphate + NADH
-
-
-
?
inosine 5'-phosphate + 3-acetylpyridine adenine dinucleotide + H2O
xanthosine 5'-phosphate + reduced 3-acetylpyridine adenine dinucleotide
-
-
?
inosine 5'-phosphate + acetylpyridine adenine dinucleotide + H2O
xanthosine 5'-phosphate + reduced acetylpyridine adenine dinucleotide
inosine 5'-phosphorothioate + NAD+ + H2O
xanthosine 5'-phosphorothioate + NADH
-
-
-
?
inosine 5'-triphosphate + NAD+ + H2O
xanthosine 5'-triphosphate + NADH
-
-
-
?
IMP + NAD+ + H2O
XMP + NADH + H+
-
rate-limiting enzyme in the de novo purine biosynthetic pathway leading to the formation of guanine ribonucleotides
-
?
IMP + NAD+ + H2O
XMP + NADH + H+
-
rate-limiting enzyme in the de novo purine biosynthetic pathway leading to the formation of guanine ribonucleotides
-
?
IMP + NAD+ + H2O
XMP + NADH + H+
-
-
?
inosine 5'-diphosphate + NAD+ + H2O
xanthosine 5'-diphosphate + NADH + H+
-
-
?
inosine 5'-diphosphate + NAD+ + H2O
xanthosine 5'-diphosphate + NADH + H+
Q81W29
-
-
?
inosine 5'-diphosphate + NAD+ + H2O
xanthosine 5'-diphosphate + NADH + H+
-
-
-
?
inosine 5'-diphosphate + NAD+ + H2O
xanthosine 5'-diphosphate + NADH + H+
-
-
?
inosine 5'-diphosphate + NAD+ + H2O
xanthosine 5'-diphosphate + NADH + H+
-
xanthosine 5'-diphosphate is the only product
?
inosine 5'-phosphate + acetylpyridine adenine dinucleotide + H2O
xanthosine 5'-phosphate + reduced acetylpyridine adenine dinucleotide
-
-
-
?
inosine 5'-phosphate + acetylpyridine adenine dinucleotide + H2O
xanthosine 5'-phosphate + reduced acetylpyridine adenine dinucleotide
-
-
-
?
inosine 5'-phosphate + NAD+
xanthosine 5'-phosphate + NADH + H+
-
-
?
inosine 5'-phosphate + NAD+
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
subdomain of the enzyme is not required for catalytic activity
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
r
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
r
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
the enzyme is important for the synthesis of guanine nucleotides
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
ir
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
347905, 347912, 347918, 347931, 667473, 667935, 667965, 667976, 667980, 670881, 684706, 689355, 706815, 706817
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
ir
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis
-
ir
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
the enzyme performs the rate-limiting step in guanine nucleotide biosynthesis
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
ir
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
obligatory step in biosynthesis of nucleic acid guanine
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
enzyme is highly specific for both inosine 5'-phosphate and NAD+
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
Parainfluenza virus
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
Parainfluenza virus
-
rate-limiting step of the de novo guanine nucleotide biosynthesis, pathway overview
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
enzyme linked to proliferation and malignancy
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
ir
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
the reaction is irreversible over the range of pH 5.5 to pH 8.8, step in guanylic acid biosynthesis
-
ir
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
the reaction is irreversible over the range of pH 5.5 to pH 8.8
-
ir
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
r
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis, pathway overview
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis, pathway overview
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
IMP oxidation is the predominant metabolic route leading to ureide synthesis
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
IMPDH catalyzes a dehydrogenase reaction and a hydrolysis reaction, a redox step producing NADH and the covalent intermediate E-xanthosine 5'-monophosphate and a hydrolysis step that produces xanthosine 5'-monophosphate. The enzyme toggles between the open conformation required for the dehydrogenase reaction and the closed conformation of the hydrolase reaction by moving a mobile flap into the NAD site. The dehydrogenase and hydrolase reactions display significant differences in the host (Homo sapiens) and parasite (Cryptosporidium parvum) enzymes, in keeping with the phylogenetic and structural divergence of their active sites
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
IMPDH catalyzes a dehydrogenase reaction and a hydrolysis reaction, a redox step producing NADH and the covalent intermediate E-xanthosine 5'-monophosphate* and a hydrolysis step that produces xanthosine 5'-monophosphate. The enzyme toggles between the open conformation required for the dehydrogenase reaction and the closed conformation of the hydrolase reaction by moving a mobile flap into the NAD site. The dehydrogenase and hydrolase reactions display significant differences in the host (Homo sapiens) and parasite (Cryptosporidium parvum) enzymes, in keeping with the phylogenetic and structural divergence of their active sites
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH + H+
-
-
?
additional information
?
-
-
IMP-enzyme binding structure analysis, overview
-
?
additional information
?
-
-
IMP-enzyme binding structure analysis, overview
-
?
additional information
?
-
-
IMP-enzyme binding structure analysis, overview
-
?
additional information
?
-
-
the enzyme binds both RNA and DNA in vitro and in vivo
-
?
additional information
?
-
-
the CBS subdomain of IMPDH coordinately regulates the adenine and guanine nucleotide pool
-
?
additional information
?
-
-
enzyme inhibition by mycophenolic acid impairs maturation and function of dendritic cells due to low GTP levels and reduced expression of CD80, CD40, CD86, CD54, and CD83 in dendritic cells, accompanied by a decreased capacity to stimulate T-lymphocytes
-
?
additional information
?
-
enzyme mutations are involved in autosomal dominant retinitis pigmentosa, pathological mechanism, overview
-
?
additional information
?
-
-
increased activities of IMP DH and GMP synthase and in the elevated concentrations of guanylates in hepatomas and other tumor cells
-
?
additional information
?
-
-
inhibition of the enzyme in K562 cells sensitizes the before resistant cells to methotrexate
-
?
additional information
?
-
-
isozyme IMPDH-1 is essential for T lymphocyte development, enzyme inhibitor mycophenolic acid inhibits tumor-associated angiogenesis
-
?
additional information
?
-
-
the enzyme is rate-limiting in the de novo synthesis of guanine nucleotides
-
?
additional information
?
-
ssDNA and RNA binding of wild-type and mutant IMPDH1s
-
?
additional information
?
-
-
the enzyme binds both RNA and DNA in vitro and in vivo
-
?
additional information
?
-
-
the enzyme interacts with GTP which leads to formation of linear arrays, GTP reverses the enzyme aggregation by inhibitor mycophenolic acid
-
?
additional information
?
-
assay method optimization. XMP detection and quantification by anion exchange chromatography
-
?
additional information
?
-
assay method optimization. XMP detection and quantification by anion exchange chromatography
-
?
additional information
?
-
-
assay method optimization. XMP detection and quantification by anion exchange chromatography
-
?
additional information
?
-
-
increased activities of IMP DH and GMP synthase and in the elevated concentrations of guanylates in hepatomas and other tumor cells
-
?
additional information
?
-
the parasite damages fetuses in utero and threatens immunocompromized individuals
-
?
additional information
?
-
-
the parasite damages fetuses in utero and threatens immunocompromized individuals
-
?
additional information
?
-
-
the enzyme binds both RNA and DNA in vitro and in vivo
-
?
additional information
?
-
-
IMP- and XMP-enzyme binding structure analysis, overview
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
IMP + NAD+ + H2O
XMP + NADH + H+
-
rate-limiting enzyme in the de novo purine biosynthetic pathway leading to the formation of guanine ribonucleotides
-
-
?
IMP + NAD+ + H2O
XMP + NADH + H+
-
rate-limiting enzyme in the de novo purine biosynthetic pathway leading to the formation of guanine ribonucleotides
-
-
?
IMP + NAD+ + H2O
XMP + NADH + H+
-
-
-
?
inosine 5'-diphosphate + NAD+ + H2O
xanthosine 5'-diphosphate + NADH + H+
-
-
-
?
inosine 5'-diphosphate + NAD+ + H2O
xanthosine 5'-diphosphate + NADH + H+
-
xanthosine 5'-diphosphate is the only product
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
subdomain of the enzyme is not required for catalytic activity
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
r
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
r
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
the enzyme is important for the synthesis of guanine nucleotides
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis
-
-
ir
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
the enzyme performs the rate-limiting step in guanine nucleotide biosynthesis
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
obligatory step in biosynthesis of nucleic acid guanine
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
Parainfluenza virus
-
rate-limiting step of the de novo guanine nucleotide biosynthesis, pathway overview
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
enzyme linked to proliferation and malignancy
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
the reaction is irreversible over the range of pH 5.5 to pH 8.8, step in guanylic acid biosynthesis
-
-
ir
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
-
-
-
r
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis, pathway overview
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
rate-limiting step of the de novo guanine nucleotide biosynthesis, pathway overview
-
-
?
inosine 5'-phosphate + NAD+ + H2O
xanthosine 5'-phosphate + NADH
-
IMP oxidation is the predominant metabolic route leading to ureide synthesis
-
-
?
additional information
?
-
-
enzyme inhibition by mycophenolic acid impairs maturation and function of dendritic cells due to low GTP levels and reduced expression of CD80, CD40, CD86, CD54, and CD83 in dendritic cells, accompanied by a decreased capacity to stimulate T-lymphocytes
-
-
?
additional information
?
-
enzyme mutations are involved in autosomal dominant retinitis pigmentosa, pathological mechanism, overview
-
-
?
additional information
?
-
-
increased activities of IMP DH and GMP synthase and in the elevated concentrations of guanylates in hepatomas and other tumor cells
-
-
?
additional information
?
-
-
inhibition of the enzyme in K562 cells sensitizes the before resistant cells to methotrexate
-
-
?
additional information
?
-
-
isozyme IMPDH-1 is essential for T lymphocyte development, enzyme inhibitor mycophenolic acid inhibits tumor-associated angiogenesis
-
-
?
additional information
?
-
-
the enzyme is rate-limiting in the de novo synthesis of guanine nucleotides
-
-
?
additional information
?
-
-
increased activities of IMP DH and GMP synthase and in the elevated concentrations of guanylates in hepatomas and other tumor cells
-
-
?
additional information
?
-
the parasite damages fetuses in utero and threatens immunocompromized individuals
-
-
?
additional information
?
-
-
the parasite damages fetuses in utero and threatens immunocompromized individuals
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3-acetylpyridine adenine dinucleotide
the NAD+ analog 3-acetylpyridine adenine dinucleotide (APAD+) is a substrate for MtIMPDH and the dependence of velocity on increasing concentrations of APAD+ (Fig. 4B) also displayed substrate inhibition
NAD+
-
-
NAD+
-
-
347905, 347912, 347916, 347918, 347931, 667473, 667921, 667935, 667937, 667965, 667980, 668351, 670881, 701583, 702243, 703271, 706815, 706817
NAD+
-
-
NAD+
-
B-sided stereospecificity: 2-3H of IMP is transferred to pro-S position of carbon atom C-4 of the nicotinamide ring in NAD+
NAD+
-
B-sided stereospecificity: 2-3H of IMP is transferred to pro-S position of carbon atom C-4 of the nicotinamide ring in NAD+
NAD+
-
NAD+ promotes the nucleophilic attack of Cys319 on IMP, the NAD+ site may be an exploitable target for the design of antimicrobial drugs
NAD+
-
preferred cofactor, NADP+ shows poor activity, less that 10% compared to NAD+
NAD+
comparison between the NAD+ binding sites of human IMPDHs and Mycobacterium tuberculosis IMPDH
NAD+
-
comparison between the NAD+ binding-sites of human IMPDHs and Mycobacterium tuberculosis IMPDH
NAD+
dependent on, binding structure to CBS domain-deleted enzyme mutant of MtbIMPDH2DELTACBS
NAD+
groups with pK values of 7.5 and 9.0 are important for NAD+ binding
additional information
involvement of three conserved water molecules (W(L), W(M), and W(C)) in the recognition of catalytic residues (R 322, D 364, and N 303) to cofactor
-
additional information
-
involvement of three conserved water molecules (W(L), W(M), and W(C)) in the recognition of catalytic residues (R 322, D 364, and N 303) to cofactor
-
additional information
the enzyme shows a clear preference for NAD+ over NADP+, since it loses more than 95% activity when using the latter as co-substrate
-
additional information
-
the enzyme shows a clear preference for NAD+ over NADP+, since it loses more than 95% activity when using the latter as co-substrate
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Cs+
K+
MgATP2-
Na+
NaCl
-
activity at 2 M NaCl is more than 4fold higher than that in the absence of salt
NH4+
Rb+
Tl+
additional information
K+
-
enhances inosine 5'-phosphate bound at a stoichiometry of four sites per tetramer and the affinity of the type 2 isozyme by 2fold
K+
required, activates, the enzyme contains one K+ per subunit
K+
-
strong activation, the K+ site is observed at the subunit interface, the activation is linked to NAD+
K+
-
activates, Km: 1.6 mM, the activation is competitively inhibited by Mg2+
MgATP2-
Q81W29
has a positive effector of IMPDHpa acting on the maximal rate and on the affinity for IMP. The positive effector binds onto the two CBS modules, with consequences on the global shape
MgATP2-
-
MgATP2- has no effect on the catalytic activity of class II IMPDHsa, but has a role in the modulation of the quaternary structure of class II IMPDHs
MgATP2-
MgATP2- has a drastic impact on the kinetic properties of class I IMPDHs. It increases the thermostability of the enzyme, is a positive effector for the cooperative class I IMPDH IMPDHpp
MgATP2-
a positive effector for the cooperative class I IMPDH IMPDHnm
MgATP2-
allosteric regulation of Pseudomonas aeruginosa IMPDH by MgATP2-
MgATP2-
MgATP2- has no effect on the catalytic activity of class II IMPDHsa, but has a role in the modulation of the quaternary structure of class II IMPDHs
additional information
MgATP has no significant effect on the catalytic activity of IMPDHbt
additional information
-
inosine 5'-phosphate binding is not altered by K+
additional information
the enzyme activity is dependent on the presence of a monovalent cation, preferaby K+. Neither Na+ nor Li+, which have lower ionic radii than K+, activate the MtIMPDH. Divalent cations, such as Mg2+ and Ca2+, do not activate the enzyme even at 200 mM
additional information
influence of various metal ions on enzyme activity
additional information
-
influence of various metal ions on enzyme activity
additional information
-
100-800 mM K+ does not affect the R418A mutant activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(propylcarbamoyl)cyclohexyl (4E)-6-[4-(acetyloxy)-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-4-methylhex-4-enoate
-
(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-[4-(4-methyl-1,3-oxazol-5-yl)phenyl]prop-2-enamide
-
isozyme IMPDH II IC50: 0.002 mM
(2E)-3-{3-[N''-cyano-N'-(4-cyano-3-methoxyphenyl)carbamimidamido]phenyl}prop-2-enoic acid
-
(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-enal
-
(2E)-4-[4-(acetyloxy)-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-2-methylbut-2-enoic acid
-
(2E)-4-{6-methoxy-7-methyl-3-oxo-4-[2-(trimethylsilyl)ethoxy]-1,3-dihydro-2-benzofuran-5-yl}-2-methylbut-2-enal
-
(2E)-N-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)-3-phenylprop-2-enamide
-
(2E)-N-hydroxy-3-[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]prop-2-enamide
-
(2E)-N-hydroxy-3-[4-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]prop-2-enamide
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(2,3-dihydro-1-benzofuran-7-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(2-acetyl-1-methyl-2,3-dihydro-1H-benzimidazol-4-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(2-methoxyquinoxalin-5-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(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
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(2H-1,3-benzodioxol-5-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(3,4-dimethoxybenzene-1-sulfonyl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(3-methoxy-4-methylphenyl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(3-methoxyquinoxalin-5-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(4-cyano-3-methoxyphenyl)carbamoyl]amino}phenyl)ethyl]carbamate
i.e. VX-4997
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(4-methyl-2,3-dihydro-1-benzofuran-6-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(5,6-dihydro-1,4-dioxin-2-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(6,7-dimethoxynaphthalen-1-yl)carbamoyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(E)-1-(3,4-dimethoxyanilino)-2-nitroethenyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[(E)-1-(4-cyano-3-methoxyanilino)-2-nitroethenyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[4-(4-cyano-3-methoxyphenyl)piperazine-1-carbonyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[5-(4-cyano-3-methoxyphenyl)-1H-benzimidazol-2-yl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-(3-{[6-(4-cyano-3-methoxyphenyl)pyrazine-2-carbonyl]amino}phenyl)ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-{3-[2-(3,4-dimethoxyphenoxy)acetamido]phenyl}ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-{3-[2-(4-cyano-3-methoxyphenoxy)acetamido]phenyl}ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-{3-[3-(4-cyano-3-methoxyphenyl)-2,4-dioxoimidazolidin-1-yl]phenyl}ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl [(1S)-1-{3-[N'-(3,4-dimethoxyphenyl)carbamimidamido]phenyl}ethyl]carbamate
-
(2R)-1-cyanobutan-2-yl {(1S)-1-[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]ethyl}carbamate
-
(2R)-1-cyanobutan-2-yl {(1S)-1-[3-({[3-methoxy-4-(morpholin-4-yl)phenyl]carbamoyl}amino)phenyl]ethyl}carbamate
-
(2R)-1-cyanobutan-2-yl {(1S)-1-[3-({[3-methoxy-4-(oxan-4-yl)phenyl]carbamoyl}amino)phenyl]ethyl}carbamate
-
(2R)-1-cyanobutan-2-yl {(1S)-1-[3-({[4-(3,6-dihydro-2H-pyran-4-yl)-3-methoxyphenyl]carbamoyl}amino)phenyl]ethyl}carbamate
-
(2R)-1-cyanobutan-2-yl-[(1S)-1-(3-{[(3,4-dimethoxyphenyl)carbamoyl]amino}phenyl)-ethyl] carbamate
-
(2R)-2-phenyl-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
(2S)-1-cyanobutan-2-yl [(1R)-1-(3-{[(3,4-dimethoxyphenyl)carbamothioyl]amino}phenyl)ethyl]carbamate
-
(2S)-1-cyanobutan-2-yl [(1R)-1-(3-{[(4-cyano-3-methoxyphenyl)carbamothioyl]amino}phenyl)ethyl]carbamate
-
(2S)-1-cyanobutan-2-yl [(1R)-1-{3-[N''-cyano-N'-(4-cyano-3,5-dimethoxyphenyl)carbamimidamido]phenyl}ethyl]carbamate
-
(2S)-1-cyanobutan-2-yl [(1R)-1-{3-[N'-(3,4,5-trimethoxyphenyl)carbamimidamido]phenyl}ethyl]carbamate
-
(2S)-1-cyanobutan-2-yl [(1R)-1-{3-[N'-(4-cyano-3,5-dimethoxyphenyl)carbamimidamido]phenyl}ethyl]carbamate
-
(2S)-2-(2,3-dichlorophenoxy)-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
(2S)-2-(2,3-dichlorophenoxy)-N-[2-(pyridin-4-yl)-1,3-benzoxazol-6-yl]propanamide
-
(2S)-2-(2,3-dimethoxyphenoxy)-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
(2S)-2-(2-chloro-3-nitrophenoxy)-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
(2S)-2-(2-chlorophenoxy)-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
(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
(3aR,4R,6S,7aR)-6-hydroxy-2,2-dimethyl-6-(propylcarbamoyl)hexahydro-2H-1,3-benzodioxol-4-yl (4E)-6-[4-(acetyloxy)-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-4-methylhex-4-enoate
-
(3aR,4R,7S,8aR)-7-hydroxy-2,2-dimethyltetrahydro-2H-4,7-methano[1,3]dioxolo[4,5-c]oxepin-6(4H)-one
-
(3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethyl-N-propylhexahydro-2H-1,3-benzodioxole-5-carboxamide
-
(3S)-oxolan-3-yl {[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]methyl}carbamate
(3S,4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-3,4-dimethylhex-4-enoic acid
-
(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde
-
(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-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-N-(1H-1,2,4-triazol-5-yl)hex-4-enamide
-
(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-N-{[(1-nitro-4a,9a-dihydroacridin-9-yl)amino]methyl}hex-4-enamide
-
(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-N-{[(4-nitro-9-oxo-4a,9,9a,10-tetrahydroacridin-1-yl)amino]methyl}hex-4-enamide
-
(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enal
-
(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enamide
-
(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
-
(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
(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
(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methyl-N-(1,3,4-thiadiazol-2-yl)hex-4-enamide
(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methyl-N-(1H-1,2,4-triazol-5-yl)hex-4-enamide
(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methyl-N-(1H-tetrazol-5-yl)hex-4-enamide
(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methyl-N-(4H-1,2,4-triazol-4-yl)hex-4-enamide
(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methyl-N-(pyridin-2-yl)hex-4-enamide
(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methyl-N-(thiazol-2-yl)hex-4-enamide
(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enethioic S-acid
(E)-N-hydroxy-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enamide
(E)-N-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]-1-(thiophen-2-yl)methanimine
-
(R,E)-7-hydroxy-5-methoxy-4-methyl-6-(3-methyl-6-(oxiran-2-yl)-6-oxohex-2-en-1-yl)isobenzofuran-1(3H)-one
(S,E)-7-hydroxy-5-methoxy-4-methyl-6-(3-methyl-6-(oxiran-2-yl)-6-oxohex-2-en-1-yl)isobenzofuran-1(3H)-one
([[(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
({hydroxy[2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethoxy]phosphoryl}methyl)phosphonic acid
-
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-methyl-6-[(5-phenyl-1,3-oxazol-2-yl)amino]-1H-indole-3-carbonitrile
-
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-[3,4-bis(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl]ethane-1,2-diyl diacetate
-
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
1-{5-O-[hydroxy({hydroxy[2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethoxy]phosphoryl}methyl)phosphoryl]-beta-D-ribofuranosyl}-1H-benzimidazol-4-amine
-
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
2'-methylthiazole-4-carboxamide adenine dinucleotide
-
noncompetitive inhibition, less cytotoxic against K562 tumor cells
2,2,2-trichloroethyl (1-oxo-1,3-dihydro-2-benzofuran-5-yl)carbamate
-
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-2-yl)-1H-indole-3-carbaldehyde
-
2-(1-benzothiophen-3-yl)-6-methoxy-5-(1,3-oxazol-5-yl)-1H-indole-3-carbaldehyde
-
2-(2,4-dichlorophenoxy)-N-[2-(pyridin-2-yl)-1,3-benzoxazol-5-yl]propanamide
-
2-(2-chlorophenoxy)-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
2-(4-methoxyphenoxy)-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
2-(dimethylamino)-7-methoxy-6-(1,3-oxazol-5-yl)quinolin-4(1H)-one
-
isozyme IMPDH II IC50: 200 nM
2-(methyl{2-[(2lambda~5~-triaza-1,2-dien-2-yl)acetyl]phenyl}amino)-2-oxoethyl acetate
-
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 5'-phosphate
-
RTC monophosphate
2-chloro-5-[[(2-[3-[(1Z)-N-hydroxyethanimidoyl]phenyl]propan-2-yl)carbamoyl]amino]-N,N-dimethylbenzamide
-
2-chloro-5-[[(2-[3-[(1Z)-N-hydroxyethanimidoyl]phenyl]propan-2-yl)carbamoyl]amino]benzamide
-
2-chloro-N,N-diethyl-5-[[(2-[3-[(1Z)-N-hydroxyethanimidoyl]phenyl]propan-2-yl)carbamoyl]amino]benzamide
-
2-chloro-N,N-dimethyl-5-[([2-[3-(prop-1-en-2-yl)phenyl]propan-2-yl]carbamoyl)amino]benzamide
noncompetitive inhibitor, that has similar affinity to both E-IMP and E-XMP, enzyme binding structure analysis, overview
2-chloro-N-methyl-5-[[[1-methyl-1-[3-(1-methylethenyl)phenyl]ethyl]amino]carbonyl]aminobenzamide
2-cyano-1-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]-3-phenylguanidine
-
isozyme IMPDH II IC50: 240 nM
2-ethyl-5'-O-[hydroxy({hydroxy[2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethoxy]phosphoryl}methyl)phosphoryl]adenosine
-
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-phenoxy-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]propanamide
-
2-tert-butyl-7-methoxy-6-(1,3-oxazol-5-yl)quinolin-4(1H)-one
-
isozyme IMPDH II IC50: 0.01 mM
2-[(2-{2-[3-methoxy-4-(1,3-oxazol-5-yl)anilino]-1,3-oxazol-5-yl}phenyl)(methyl)amino]-2-oxoethyl acetate
-
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'-[N''-cyano-N'-(4-cyano-3-methoxyphenyl)carbamimidamido][1,1'-biphenyl]-3-carboxylic acid
-
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
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-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-phenyl quinolone derivatives
-
several, isozyme IMPDH II IC50: 5-160 nM, overview
-
3-{3-[N''-cyano-N'-(4-cyano-3-methoxyphenyl)carbamimidamido]phenyl}propanoic acid
-
4-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]amino]-6-phenyl-1,3,5-triazin-2-ol
-
5'-deoxy-5'-[(3-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]amino}-2-oxopropyl)amino]adenosine
-
5'-O-([1-[(2E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-methylbut-2-en-1-yl]-1H-1,2,3-triazol-4-yl]methyl)adenosine
an uncompetitive inhibitor with a strong preference for the E-XMP reaction intermediate, enzyme binding structure analysis, overview
5'-O-({[2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]sulfamoyl}methanesulfonyl)adenosine
-
5'-O-[hydroxy({hydroxy[2-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethoxy]phosphoryl}methyl)phosphoryl]adenosine
-
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-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-{(2E)-4-[4-({[(2S,5R)-5-(6-amino-7,8-dihydro-9H-purin-9-yl)oxolan-2-yl]methoxy}methyl)-1H-1,2,3-triazol-1-yl]-3-methylbut-2-en-1-yl}-7-hydroxy-5-methoxy-4-methyl-2-benzofuran-1(3H)-one
-
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-4-methyl-6-[(2E)-3-methyl-4-(2lambda~5~-triaza-1,2-dien-2-yl)but-2-en-1-yl]-2-benzofuran-1(3H)-one
-
7-hydroxy-5-methoxy-4-methyl-6-{(2E)-3-methyl-6-[(2R)-oxiran-2-yl]-6-oxohex-2-en-1-yl}-2-benzofuran-1(3H)-one
-
7-hydroxy-5-methoxy-4-methyl-6-{(2E)-3-methyl-6-[(2S)-oxiran-2-yl]-6-oxohex-2-en-1-yl}-2-benzofuran-1(3H)-one
-
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-hydroxy-6-[(2E)-6-hydroxy-3-methylocta-2,7-dien-1-yl]-5-methoxy-4-methyl-2-benzofuran-1(3H)-one
-
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)-3-[2-(pyridin-4-yl)ethyl]-2-sulfanylidene-2,3-dihydroquinazolin-4(1H)-one
-
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
APAD+
substrate inhibition, uncompetitive substrate inhibition versus IMP
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
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
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
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 1-{(2Z)-2-[3,4-bis(benzyloxy)-5-oxofuran-2(5H)-ylidene]ethyl}-4,5-dihydro-1H-imidazole-4,5-dicarboxylate
-
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
ethyl (2E)-3-[3-methoxy-4-(1,3-oxazol-5-yl)anilino]-3-phenylprop-2-enoate
-
ethyl (2E)-3-[4-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]prop-2-enoate
-
ethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl carbonate
-
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
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 N-[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]alaninate
-
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 glucuronide
-
80% inhibition at 0.2 mM, human plasma or serum reduces the inhibition
mycophenolic hydroxamic acid
-
comparison with inhibition of histone deacetylase and K562 cell proliferation
N''-cyano-N-(3'-cyano[1,1'-biphenyl]-3-yl)-N'-(4-cyano-3-methoxyphenyl)guanidine
-
N''-cyano-N-(4'-cyano[1,1'-biphenyl]-3-yl)-N'-(4-cyano-3-methoxyphenyl)guanidine
-
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-(2'-fluoro[1,1'-biphenyl]-3-yl)guanidine
-
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-(3'-fluoro[1,1'-biphenyl]-3-yl)guanidine
-
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-(4'-fluoro[1,1'-biphenyl]-3-yl)guanidine
-
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-[3'-(trifluoromethyl)[1,1'-biphenyl]-3-yl]guanidine
-
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-[3-(1-hydroxyethenyl)phenyl]guanidine
-
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-[3-(2-hydroxyprop-2-en-1-yl)phenyl]guanidine
-
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-[3-(2-methyl-2H-tetrazol-5-yl)phenyl]guanidine
-
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-{3-[(1-methyl-1H-tetrazol-5-yl)methyl]phenyl}guanidine
-
N''-cyano-N-(4-cyano-3-methoxyphenyl)-N'-{3-[(2-methyl-2H-tetrazol-5-yl)methyl]phenyl}guanidine
-
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-(2-{2-[3-methoxy-4-(1,3-oxazol-5-yl)anilino]-1,3-oxazol-5-yl}phenyl)-N-methyl-2-(morpholin-4-yl)acetamide
-
N-(2-{3-[(1E)-N-(2-aminoethoxy)ethanimidoyl]phenyl}propan-2-yl)-N'-(4-chloro-3-nitrophenyl)urea
an inhibitor with in vivo anticryptosporidial activity, binding structure determination and analysi, P131 contains two aromatic groups, one of which interacts with the hypoxanthine ring of IMP, while the second interacts with the aromatic ring of a tyrosine in the adjacent subunit. In addition, the amine and NO2 moieties bind in hydrated cavities, forming water-mediated hydrogen bonds to the proteins. The oxime group of P131 lies across the hypoxanthine ring of IMP, while the N5 amine forms hydrogen bonds to the main chain carbonyl O atom of Gly212 and N3 of IMP in all of the subunits
N-(4-chloro-3-methoxyphenyl)-2-(4-oxo[1]benzopyrano[4,3-c]pyrazol-1(4H)-yl)acetamide
-
N-(4-chlorophenyl)-2-phenoxypropanamide
antagonizes ADP binding
N-(4-methoxyphenyl)-2-naphthalen-1-ylacetamide
binds in the nicotinamide subsite and does not interact with ADP
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-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-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-[(4-fluorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]-2-methyl-3-(1,2,4-thiadiazol-5-yl)-1H-indole-6-carboxamide
-
N-[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]alanine
-
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-(morpholine-4-carbonyl)phenyl]-N'-(2-[3-[(1Z)-N-hydroxyethanimidoyl]phenyl]propan-2-yl)urea
-
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
N-{2-[6-(4-ethylpiperazin-1-yl)pyridin-3-yl]propan-2-yl}-2-fluoro-9-oxo-4a,9,9a,10-tetrahydroacridine-3-carboxamide
-
N-{2-[6-(4-ethylpiperazin-1-yl)pyridin-3-yl]propan-2-yl}-2-fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide
-
N1-methyl-N~2~-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethanediamide
-
N2-(2,3-dichlorophenyl)-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]-L-alaninamide
a competitive inhibitor versus NAD+, that has a strong preference for E-IMP, enzyme binding structure analysis, overview
nicotinic acid
-
inhibitory analog of NAD+, non-competitive with respect to IMP and K+
N~1~-hydroxy-N~8~-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]octanediamide
-
N~2~-(2,3-dichlorophenyl)-N-[2-(pyridin-4-yl)-1,3-benzoxazol-5-yl]alaninamide
-
oxolan-3-yl {[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]methyl}carbamate
-
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-(tiazofurin-5'-yl)-P2-(2-aminoadenosin-5'-yl) diphosphate
-
comparison with inhibition of alcohol dehydrogenase, malate dehydrogenase, lactate dehydrogenase and K562 cell proliferation