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3.5.4.10: IMP cyclohydrolase

This is an abbreviated version!
For detailed information about IMP cyclohydrolase, go to the full flat file.

Word Map on EC 3.5.4.10

Reaction

IMP
+
H2O
=
5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide

Synonyms

5-aminoimidazole-4-carboxamide ribonucleotide formyltransferase/IMP cyclohydrolase, 5-aminoimidazole-4-carboxamide ribonucleotide tranformylase/IMP cyclohydrolase, AF1811, AICAR tranformylase/IMP cyclohydrolase, AICAR transformylase/IMP cyclohydrolase, AICAR transformylase/inosine 5'-monophosphate cyclohydrolase, AICAR-FT/IMP-CHase, AICAR-transformylase/IMP cyclohydrolase, ATIC, atic-1, IMP synthetase, IMPCH, IMPCHase, inosinate cyclohydrolase, inosine 5'-monophosphate cyclohydrolase, inosine monophosphate cyclohydrolase, inosinicase, ITGA2, MjPurO, MthPurO, PurH, PurH2, PurH2-type IMP cyclohydrolase, PurO, PurO-type IMP cyclohydrolase, TK0430

ECTree

     3 Hydrolases
         3.5 Acting on carbon-nitrogen bonds, other than peptide bonds
             3.5.4 In cyclic amidines
                3.5.4.10 IMP cyclohydrolase

Inhibitors

Inhibitors on EC 3.5.4.10 - IMP cyclohydrolase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2'-deoxy-AMP
-
decreased IMP cyclohydrolase activity by 10-50%
2,2-dioxo-1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4(3H)-one
construction of 1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxide, the corresponding nucleoside, and the nucleoside monophosphate, as mimics of the tetrahedral intermediate in the cyclization reaction. All compounds are competitive inhibitors against IMPCH, but the simpler heterocycle has a completely different IMPCH binding mode, compared to the nucleosides, and is relocated to the phosphate binding pocket, the aromatic imidazole ring interacts with a helix dipole, inhibitor synthesis, binding structure, and mechanism of inhibition, overview
2-chloroinosine 5'-monophosphate
-
potent inhibitor
2-flouroinosine 5'-monophosphate
-
IC50-value in cell culture 0.0049 mM; potent inhibitor
2-fluoroadenine arabinoside 5'-monophosphate
2-mercaptoinosine 5'-monophosphate
-
most potent competitive inhibitor, precursor of GMP in the purine pathway
5-aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside
-
decreased IMP cyclohydrolase activity by 10-50%
6-mercaptopurine riboside 5'-monophosphate
7-(3,4-dihydroxy-5-hydroxymethyltetrahydrofuran-2-yl)-2,2-dioxo-1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4(3H)-one
construction of 1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxide, the corresponding nucleoside, and the nucleoside monophosphate, as mimics of the tetrahedral intermediate in the cyclization reaction. All compounds are competitive inhibitors against IMPCH, but the simpler heterocycle has a completely different IMPCH binding mode, compared to the nucleosides, and is relocated to the phosphate binding pocket, the aromatic imidazole ring interacts with a helix dipole, inhibitor synthesis, binding structure, and mechanism of inhibition, overview
adenosine N1-oxide 5'-monophosphate
AMP
-
decreased IMP cyclohydrolase activity by 10-50%
GMP
-
decreased IMP cyclohydrolase activity by 10-50%
N-succino-AMP
-
decreased IMP cyclohydrolase activity by 10-50%
N2-acetyl-2'deoxyguanosine 5'-monophosphate
-
decreased IMP cyclohydrolase activity by 10-50%
N6-(carboxymethyl)adenosine 5'-monophosphate
-
strong competitive inhibitor
phosphoric acid mono-[3,4-dihydroxy-5-(2,2,4-trioxo-1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-7-yl)tetrahydrofuran-2-yl]methyl ester
construction of 1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxide, the corresponding nucleoside, and the nucleoside monophosphate, as mimics of the tetrahedral intermediate in the cyclization reaction. All compounds are competitive inhibitors against IMPCH, but the simpler heterocycle has a completely different IMPCH binding mode, compared to the nucleosides, and is relocated to the phosphate binding pocket, the aromatic imidazole ring interacts with a helix dipole, inhibitor synthesis, binding structure, and mechanism of inhibition, overview
xanthosine 5'-monophosphate
-
strong competitive inhibitor
additional information
-