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Escherichia coli K-12 substr. MG1655 Compound: IMP

Synonyms: 5'-IMP, ribosylhypoxanthine monophosphate, inosinate, inosine monophosphate, inosine 5'-monophosphate, inosine 5'-phosphate, 5'-inosinate, 5'-inosinic acid, 5'-inosine monophosphate

Superclasses: a nucleic acid component a nucleotide a nucleoside 5'-monophosphate a ribonucleoside 5'-monophosphate a purine ribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a purine nucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a ribonucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a ribonucleotide a ribonucleoside 5'-monophosphate a purine ribonucleoside 5'-monophosphate
a nucleic acid component
an organic heterocyclic compound an organic heterobicyclic compound a purine a purine nucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a purine a purine nucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate

Chemical Formula: C10H11N4O8P

Molecular Weight: 346.19 Daltons

Monoisotopic Molecular Weight: 348.04709992489995 Daltons

SMILES: C(OP(=O)([O-])[O-])C1(OC(C(O)C(O)1)N3(C=NC2(C(=O)NC=NC=23)))

InChI: InChI=1S/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/p-2/t4-,6-,7-,10-/m1/s1

InChIKey: InChIKey=GRSZFWQUAKGDAV-KQYNXXCUSA-L

Unification Links: CAS:131-99-7 , ChEBI:58053 , ChemSpider:5482599 , HMDB:HMDB00175 , IAF1260:33960 , KEGG:C00130 , MetaboLights:MTBLC58053 , PubChem:7140378

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -356.039

Reactions known to consume the compound:

adenosine ribonucleotides de novo biosynthesis :
L-aspartate + IMP + GTP → adenylo-succinate + GDP + phosphate + 2 H+

guanosine ribonucleotides de novo biosynthesis :
IMP + NAD+ + H2O → XMP + NADH + H+

Not in pathways:
IMP + H2O → inosine + phosphate


a ribonucleoside 5'-monophosphate + H2O → a ribonucleoside + phosphate


a nucleoside 5'-monophosphate[periplasmic space] + H2O[periplasmic space] → a nucleoside[periplasmic space] + phosphate[periplasmic space]

Reactions known to produce the compound:

adenine and adenosine salvage III :
IMP + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + hypoxanthine

adenine and adenosine salvage V :
inosine + ATP → IMP + ADP + H+

Not in pathways:
ITP + H2O → IMP + diphosphate + H+
ammonium + IMP + NADP+ ← GMP + NADPH + 2 H+

tRNA processing :
a tRNA precursor with a 5' extension and a long 3' trailer + H2O → a tRNA precursor with a 5' extension + a ribonucleoside 5'-monophosphate
a tRNA precursor with a 5' extension and a short 3' extension → a tRNA precursor with a 5' extension + a ribonucleoside 5'-monophosphate


a single stranded DNA + H2O → a ribonucleoside 5'-monophosphate + a single-stranded oligodeoxyribonucleotide

tRNA processing :
a tRNA precursor with a 5' extension and a long 3' trailer + n H2O → a tRNA precursor with a 5' extension and a short 3' extension + n a nucleoside 5'-monophosphate
a tRNA precursor with a short 3' extension → an uncharged tRNA + n a nucleoside 5'-monophosphate


a tRNA precursor + H2O → a tRNA + a nucleoside 5'-monophosphate
RNase R degradation substrate RNA + n-1 H2O → n-2 a nucleoside 5'-monophosphate + a diribonucleotide
an oligonucleotide + H2O → n a nucleoside 5'-monophosphate
RNA + n H2O → n a nucleoside 5'-monophosphate
DNAn + n H2O → n a nucleoside 5'-monophosphate
a nucleoside diphosphate + H2O → a nucleoside 5'-monophosphate + phosphate + H+
a RNA-DNA hybrid + n H2O → DNA + n a nucleoside 5'-monophosphate
a nucleoside triphosphate + H2O → a nucleoside 5'-monophosphate + diphosphate + H+
RNase II degradation substrate mRNA + n H2O → n a nucleoside 5'-monophosphate
mutated tRNA + n H2O → n a nucleoside 5'-monophosphate
(deoxynucleotides)(n) + H2O → (deoxynucleotides)(n-1) + a nucleoside 5'-monophosphate

Reactions known to both consume and produce the compound:

inosine-5'-phosphate biosynthesis I :
IMP + H2O ↔ 5-formamido-1-(5-phospho-D-ribosyl)-imidazole-4-carboxamide

In Transport reactions:
IMP[cytosol]IMP[periplasmic space]

Enzymes activated by IMP, sorted by the type of activation, are:

Activator (Allosteric) of: carbamoyl phosphate synthetase [Anderson77, Trotta74]

Enzymes inhibited by IMP, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: phosphoribosylaminoimidazole-succinocarboxamide synthase [Nelson05]

Inhibitor (Mechanism unknown) of: amidophosphoribosyl transferase [Messenger79] , guanylate kinase [Oeschger66] , xanthine phosphoribosyltransferase [Liu83, Comment 1] , methylenetetrahydrofolate dehydrogenase [Dev78] , hypoxanthine phosphoribosyltransferase [Hochstadt78, Guddat02]


References

Anderson77: Anderson PM (1977). "Binding of allosteric effectors to carbamyl-phosphate synthetase from Escherichia coli." Biochemistry 1977;16(4);587-93. PMID: 189806

Dev78: Dev IK, Harvey RJ (1978). "A complex of N5,N10-methylenetetrahydrofolate dehydrogenase and N5,N10-methenyltetrahydrofolate cyclohydrolase in Escherichia coli. Purification, subunit structure, and allosteric inhibition by N10-formyltetrahydrofolate." J Biol Chem 1978;253(12);4245-53. PMID: 350870

Guddat02: Guddat LW, Vos S, Martin JL, Keough DT, de Jersey J (2002). "Crystal structures of free, IMP-, and GMP-bound Escherichia coli hypoxanthine phosphoribosyltransferase." Protein Sci 11(7);1626-38. PMID: 12070315

Hochstadt78: Hochstadt J (1978). "Hypoxanthine phosphoribosyltransferase and guanine phosphoribosyltransferase from enteric bacteria." Methods Enzymol 1978;51;549-58. PMID: 692401

Liu83: Liu SW, Milman G (1983). "Purification and characterization of Escherichia coli guanine-xanthine phosphoribosyltransferase produced by a high efficiency expression plasmid utilizing a lambda PL promoter and CI857 temperature-sensitive repressor." J Biol Chem 1983;258(12);7469-75. PMID: 6305942

Messenger79: Messenger LJ, Zalkin H (1979). "Glutamine phosphoribosylpyrophosphate amidotransferase from Escherichia coli. Purification and properties." J Biol Chem 1979;254(9);3382-92. PMID: 372191

Nelson05: Nelson SW, Binkowski DJ, Honzatko RB, Fromm HJ (2005). "Mechanism of action of Escherichia coli phosphoribosylaminoimidazolesuccinocarboxamide synthetase." Biochemistry 44(2);766-74. PMID: 15641804

Oeschger66: Oeschger MP, Bessman MJ (1966). "Purification and properties of guanylate kinase from Escherichia coli." J Biol Chem 1966;241(22);5452-60. PMID: 5333666

Trotta74: Trotta PP, Pinkus LM, Haschemeyer RH, Meister A (1974). "Reversible dissociation of the monomer of glutamine-dependent carbamyl phosphate synthetase into catalytically active heavy and light subunits." J Biol Chem 1974;249(2);492-9. PMID: 4358555


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Fri Dec 19, 2014, biocyc14.