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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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

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+


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


ribonucleotiden + ribonucleotiden + ATP → ribonucleotidem+n + AMP + diphosphate


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


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 → GMP + factor F420-0 + 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


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


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


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
DNAn + n H2O → n a nucleoside 5'-monophosphate
RNA + n H2O → n a nucleoside 5'-monophosphate
a double stranded DNA + H2O → a double stranded DNA + a nucleoside 5'-monophosphate
(deoxynucleotides)(n) + H2O → (deoxynucleotides)(n-1) + a nucleoside 5'-monophosphate
a RNA-DNA hybrid + n H2O → DNA + n a nucleoside 5'-monophosphate
a 2-O-methylated RNA + n H2O → n 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
an oligonucleotide + H2O → an oligonucleotide + a nucleoside 5'-monophosphate
a generic polynucleotide substrate + n H2O → n a nucleoside 5'-monophosphate
a nucleoside triphosphate + H2O → a nucleoside 5'-monophosphate + diphosphate + H+
a cyclic 3',5'-nucleoside monophosphate + H2O → a nucleoside 5'-monophosphate + H+

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


a purine ribonucleoside + diphosphate = a purine ribonucleoside 5'-monophosphate + phosphate + H+


a nucleoside 5'-monophosphate + ATP = a 5'-phosphonucleoside 3'-diphosphate + AMP + 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+


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: guanosine kinase [Comment 1] , IMP dehydrogenase [Gilbert79, Comment 2] , amidophosphoribosyl transferase [Messenger79] , 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]


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
Page generated by SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, BIOCYC14B.