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MetaCyc Compound: GMP

Synonyms: guanylate, G, guanylic acid, guanosine phosphate, guanosine 5'-phosphate, guanosine monophosphate, guanosine-5'-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: C10H12N5O8P

Molecular Weight: 361.21 Daltons

Monoisotopic Molecular Weight: 363.0579989622 Daltons

GMP compound structure

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

InChI: InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/p-2/t3-,5-,6-,9-/m1/s1

InChIKey: InChIKey=RQFCJASXJCIDSX-UUOKFMHZSA-L

Unification Links: CAS:85-32-5 , ChEBI:58115 , ChemSpider:1413162 , HMDB:HMDB01397 , IAF1260:34024 , KEGG:C00144 , MetaboLights:MTBLC58115 , PubChem:1807035

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -229.97382 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

guanosine nucleotides degradation I , guanosine nucleotides degradation II , guanosine nucleotides degradation III :
GMP + H2O → guanosine + phosphate

guanosine ribonucleotides de novo biosynthesis :
ATP + GMP → ADP + GDP

Not in pathways:
ammonium + IMP + NADP+GMP + NADPH + 2 H+

Not in pathways:
a ribonucleoside 5'-monophosphate + H2O → a ribonucleoside + phosphate

Not in pathways:
ribonucleotiden + ribonucleotiden + ATP → ribonucleotidem+n + AMP + diphosphate

Not in pathways:
a nucleoside 5'-monophosphate[periplasmic space] + H2O[periplasmic space] → a nucleoside[periplasmic space] + phosphate[periplasmic space]
a nucleoside 5'-monophosphate + ATP → a nucleoside diphosphate + ADP

Not in pathways:
a nucleotide + H2O → a nucleoside + phosphate

Reactions known to produce the compound:

adenosylcobalamin biosynthesis from cobyrinate a,c-diamide I , adenosylcobalamin salvage from cobinamide I , adenosylcobalamin salvage from cobinamide II :
adenosylcobinamide-GDP + α-ribazole 5'-phosphate → adenosylcobalamin 5'-phosphate + GMP + H+

factor 420 biosynthesis :
(2S)-lactyl-2-diphospho-5'-guanosine + 7,8-didemethyl-8-hydroxy-5-deazariboflavin → oxidized coenzyme F420-0 + GMP + H+

guanine and guanosine salvage III :
guanosine + ATP → GMP + ADP + H+

guanosine ribonucleotides de novo biosynthesis :
XMP + L-glutamine + ATP + H2O → L-glutamate + GMP + AMP + diphosphate + 2 H+

Not in pathways:
GDP + H2O → GMP + phosphate + H+
cyclic-GMP + H2O → GMP + H+
GMP-N-ε-(N-α-acetyl lysine methyl ester) 5'-phosphoramidate + H2O → GMP + N-α-acetyl lysine methyl ester
GDP-α-D-mannose + H2O → GMP + α-D-mannose 1-phosphate + 2 H+
an RNA terminal-2',3'-cyclic-phosphate + a 5'-hydroxyl terminated RNA + GTP → a ligated RNA + GMP + diphosphate
GTP + H2O → GMP + diphosphate + H+
XMP + ammonium + ATP → GMP + AMP + diphosphate + 2 H+
an RNA 3'-terminal-phosphate + GTP → an RNA terminal-2',3'-cyclic-phosphate + GMP + diphosphate
GTP + 2 H2O → GMP + 2 phosphate + 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

Not in pathways:
a single stranded DNA + H2O → a ribonucleoside 5'-monophosphate + a single-stranded oligodeoxyribonucleotide
a single-stranded RNA + n H2O → n a ribonucleoside 5'-monophosphate

Not in pathways:
a tRNA precursor + H2O → a tRNA + a ribonucleotide

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

Not in pathways:
a nucleoside 3',5'-bisphosphate + H2O → a nucleoside 5'-monophosphate + phosphate
a nucleoside triphosphate + 2 H2O → a nucleoside 5'-monophosphate + 2 phosphate + 2 H+
a tRNA precursor + H2O → a tRNA + a nucleoside 5'-monophosphate
RNase II degradation substrate mRNA + n H2O → n a nucleoside 5'-monophosphate
mutated tRNA + n H2O → n a nucleoside 5'-monophosphate

Reactions known to both consume and produce the compound:

adenosylcobalamin biosynthesis from cobyrinate a,c-diamide II :
adenosylcobinamide-GDP + α-ribazole ↔ coenzyme B12 + GMP + H+

guanine and guanosine salvage , guanine and guanosine salvage II :
GMP + diphosphate ↔ guanine + 5-phospho-α-D-ribose 1-diphosphate

In Reactions of unknown directionality:

Not in pathways:
P1,P4-bis(5'-guanosyl) tetraphosphate + H2O = GTP + GMP + 2 H+
phosphomannan(n) + GDP-α-D-mannose = phosphomannan(n+1) + GMP
(deoxynucleotides)(m) + GTP + (deoxynucleotides)(n) = (deoxynucleotides)(n+m) + GMP + diphosphate

Not in pathways:
a purine ribonucleoside + diphosphate = a purine ribonucleoside 5'-monophosphate + phosphate + H+

Not in pathways:
a nucleoside 5'-monophosphate + ATP = a 5'-phosphonucleoside 3'-diphosphate + AMP + H+
a lipopolysaccharide + a nucleoside diphosphocholine = a phosphorylcholine-6-O-hexose-lipopolysaccharide + a nucleoside 5'-monophosphate + H+
a dinucleotide (nucleic acid) + H2O = 2 a nucleoside 5'-monophosphate + 2 H+
a nucleoside diphosphate + H2O = a nucleoside 5'-monophosphate + phosphate + H+
a p-nitrophenyl 5'-nucleotide + H2O = a nucleoside 5'-monophosphate + 4-nitrophenol + 2 H+

Not in pathways:
a nucleotide + a 2'-deoxynucleoside = a nucleoside + a 2'-deoxyribonucleoside 5'-monophosphate

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

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

Activator (Mechanism unknown) of: pyruvate kinase [Singh98]

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

Inhibitor (Competitive) of: amidophosphoribosyl transferase [Messenger79] , IMP dehydrogenase [Gilbert79, Comment 1] , guanosine kinase [Comment 2] , adenylosuccinate synthetase [Comment 3]

Inhibitor (Allosteric) of: amidophosphoribosyl transferase [Messenger79, Zhou94]

Inhibitor (Mechanism unknown) of: hypoxanthine phosphoribosyltransferase [Guddat02] , guanine phosphoribosyltransferase [Deo85] , xanthine phosphoribosyltransferase [Liu83, Deo85] , chitobiosyldiphosphodolichol β-mannosyltransferase [Sharma82] , inosine kinase [Combes89] , guanosine kinase [Combes89] , glutamine:fructose-6-phosphate amidotransferase [Broschat02]

This compound has been characterized as an alternative substrate of the following enzymes: alkaline phosphatase , farnesyl diphosphate phosphatase , deoxyribonucleoside 5'-monophosphate phosphatase , AMP 5'-nucleotidase , IMP 5'-nucleotidase , 5'-nucleotidase


References

Broschat02: Broschat KO, Gorka C, Page JD, Martin-Berger CL, Davies MS, Huang Hc HC, Gulve EA, Salsgiver WJ, Kasten TP (2002). "Kinetic characterization of human glutamine-fructose-6-phosphate amidotransferase I: potent feedback inhibition by glucosamine 6-phosphate." J Biol Chem 277(17);14764-70. PMID: 11842094

Combes89: Combes, Agnes, Lafleuriel, Jacqueline, Le Floc'h, Francois (1989). "The inosine-guanosine kinase activity of mitochondria in tubers of Jerusalem artichoke." Plant Physiol. Biochem. 27(5):729-736.

Deo85: Deo SS, Tseng WC, Saini R, Coles RS, Athwal RS (1985). "Purification and characterization of Escherichia coli xanthine-guanine phosphoribosyltransferase produced by plasmid pSV2gpt." Biochim Biophys Acta 839(3);233-9. PMID: 3886014

Gilbert79: Gilbert HJ, Lowe CR, Drabble WT (1979). "Inosine 5'-monophosphate dehydrogenase of Escherichia coli. Purification by affinity chromatography, subunit structure and inhibition by guanosine 5'-monophosphate." Biochem J 1979;183(3);481-94. PMID: 44191

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

Kawasaki00: Kawasaki H, Shimaoka M, Usuda Y, Utagawa T (2000). "End-product regulation and kinetic mechanism of guanosine-inosine kinase from Escherichia coli." Biosci Biotechnol Biochem 2000;64(5);972-9. PMID: 10879466

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lipps99: Lipps G, Krauss G (1999). "Adenylosuccinate synthase from Saccharomyces cerevisiae: homologous overexpression, purification and characterization of the recombinant protein." Biochem J 1999;341 ( Pt 3);537-43. PMID: 10417315

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

Ryzhova98: Ryzhova TA, Andreichuk YV, Domkin VD (1998). "Adenylosuccinate synthetase of the yeast Saccharomyces cerevisiae: purification and properties." Biochemistry (Mosc) 1998;63(6);650-6. PMID: 9668204

Sharma82: Sharma CB, Lehle L, Tanner W (1982). "Solubilization and characterization of the initial enzymes of the dolichol pathway from yeast." Eur J Biochem 126(2);319-25. PMID: 6215245

Singh98: Singh DK, Malhotra SP, Singh R (1998). "Purification and characterizaton of plastidic pyruvate kinase from developing seeds of Brassica campestris L." Indian J Biochem Biophys 35(6);346-52. PMID: 10412228

Tiedeman85: Tiedeman AA, Smith JM (1985). "Nucleotide sequence of the guaB locus encoding IMP dehydrogenase of Escherichia coli K12." Nucleic Acids Res 1985;13(4);1303-16. PMID: 2860637

Zhou94: Zhou G, Smith JL, Zalkin H (1994). "Binding of purine nucleotides to two regulatory sites results in synergistic feedback inhibition of glutamine 5-phosphoribosylpyrophosphate amidotransferase." J Biol Chem 269(9);6784-9. PMID: 8120039


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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