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MetaCyc Compound: GTP

Synonyms: guanylyl imidodiphosphate, guanosine 5'-triphosphate, guanosine-triphosphate

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

Chemical Formula: C10H12N5O14P3

Molecular Weight: 519.15 Daltons

Monoisotopic Molecular Weight: 522.990659779 Daltons

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

InChI: InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18)/p-4/t3-,5-,6-,9-/m1/s1

InChIKey: InChIKey=XKMLYUALXHKNFT-UUOKFMHZSA-J

Unification Links: CAS:86-01-1 , ChEBI:37565 , ChemSpider:5414499 , HMDB:HMDB01273 , IAF1260:33641 , KEGG:C00044 , MetaboLights:MTBLC37565 , PubChem:7058167

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -553.3185 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

6-hydroxymethyl-dihydropterin diphosphate biosynthesis I , drosopterin and aurodrosopterin biosynthesis , preQ0 biosynthesis , tetrahydrobiopterin biosynthesis I , tetrahydrobiopterin biosynthesis II , tetrahydrobiopterin biosynthesis III :
GTP + H2O → formate + 7,8-dihydroneopterin 3'-triphosphate + H+

6-hydroxymethyl-dihydropterin diphosphate biosynthesis II (archaea) :
GTP + H2O → 7,8-dihydroneopterin 2',3'-cyclic phosphate + formate + diphosphate + H+

6-hydroxymethyl-dihydropterin diphosphate biosynthesis III (Chlamydia) , flavin biosynthesis I (bacteria and plants) , flavin biosynthesis III (fungi) :
GTP + 3 H2O → 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one + formate + diphosphate + 2 H+

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

alginate biosynthesis I , alginate biosynthesis II , GDP-mannose biosynthesis , L-ascorbate biosynthesis I (L-galactose pathway) :
α-D-mannose 1-phosphate + GTP + H+ → GDP-α-D-mannose + diphosphate

CMP-legionaminate biosynthesis I :
D-glucosamine 1-phosphate + GTP + H+ → GDP-D-glucosamine + diphosphate

factor 420 biosynthesis :
(2S)-2-phospholactate + GTP + H+ → (2S)-lactyl-2-diphospho-5'-guanosine + diphosphate
(S)-lactate + GTP → (2S)-2-phospholactate + GDP + H+

factor 420 polyglutamylation :
factor F420-0 + L-glutamate + GTP → factor γ-F420-1 + GDP + phosphate + H+
factor γ-F420-1 + L-glutamate + GTP → oxidized coenzyme γ-F420-2 + GDP + phosphate + H+

flavin biosynthesis II (archaea) :
GTP + 3 H2O → 2-amino-5-formylamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one + 2 phosphate + 2 H+

GDP-D-glycero-α-D-manno-heptose biosynthesis :
D-glycero-α-D-manno-heptose 1-phosphate + GTP + H+ → GDP-D-glycero-α-D-manno-heptose + diphosphate

GDP-glucose biosynthesis , GDP-glucose biosynthesis II :
α-D-glucose 1-phosphate + GTP + H+ → GDP-α-D-glucose + diphosphate

GDP-L-fucose biosynthesis II (from L-fucose) :
β-L-fucose 1-phosphate + GTP + H+ → GDP-L-fucose + diphosphate

guanosine deoxyribonucleotides de novo biosynthesis II :
dGTP + an oxidized flavodoxin + H2O ← GTP + a reduced flavodoxin

guanylyl molybdenum cofactor biosynthesis :
MoO2-molybdopterin cofactor + GTP + H+ → guanylyl molybdenum cofactor + diphosphate

itaconate degradation :
itaconate + GTP + coenzyme A → itaconyl-CoA + GDP + phosphate

methylthiolincosamide biosynthesis :
D-erythro-D-gluco-octose α-1-phosphate + GTP + H+ → GDP-D-erythro-α-D-gluco-octose + diphosphate

molybdenum cofactor biosynthesis :
GTP → cyclic pyranopterin phosphate + diphosphate

mRNA capping I :
a 5'-diphospho-purine-[mRNA] + GTP + H+ → a 5'-(5'-triphosphoguanosine)-purine-[mRNA] + diphosphate

oxidized GTP and dGTP detoxification :
GTP + hydroxyl radical → 8-oxo-GTP + H+

ppGpp biosynthesis :
GTP + ATP → pppGpp + AMP

toyocamycin biosynthesis :
GTP + [(1R,2R,3S,4S)-4-{5-cyano-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-7-yl}-2,3-dihydroxycyclopentyl]methyl phosphate + L-aspartate → succinylo-toyocamycin phosphate + GDP + phosphate + 2 H+

Not in pathways:
a tRNA 2-thiouridine34 + a 5,10-methylene-tetrahydrofolate + ammonium + GTP + H2O → a tRNA containing 5-aminomethyl-2-thiouridine + a 7,8-dihydrofolate + GDP + phosphate
GTP + AMP → GDP + ADP
GTP + 2 H2O → GMP + 2 phosphate + 2 H+
an RNA 3'-terminal-phosphate + GTP → an RNA terminal-2',3'-cyclic-phosphate + GMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate
GTP + H2O → GDP + phosphate + H+
2 GTP → cyclic di-3',5'-guanylate + 2 diphosphate
GTP + H2O → GMP + diphosphate + H+
an RNA terminal-2',3'-cyclic-phosphate + a 5'-hydroxyl terminated RNA + GTP → a ligated RNA + GMP + diphosphate


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

jadomycin biosynthesis :
α-D-glucose 1-phosphate + a nucleoside triphosphate + H+ → an NDP-α-D-glucose + diphosphate

phytol salvage pathway :
phytyl monophosphate + a nucleoside triphosphate → phytyl diphosphate + a nucleoside diphosphate

pyrimidine deoxyribonucleosides salvage :
2'-deoxycytidine + a nucleoside triphosphate → dCMP + a nucleoside diphosphate + H+


a nucleoside triphosphate + H2O → a nucleoside diphosphate + phosphate + H+
a nucleoside triphosphate + H2O → a nucleoside 5'-monophosphate + diphosphate + H+
a nucleoside triphosphate + 2 H2O → a nucleoside 5'-monophosphate + 2 phosphate + 2 H+


a nucleotide + H2O → a nucleoside + phosphate

Reactions known to produce the compound:

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

ppGpp biosynthesis :
GDP + ATP → GTP + ADP
pppGpp + H2O → GTP + diphosphate + H+

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


a nucleoside diphosphate + ATP → a nucleoside triphosphate + ADP

Reactions known to both consume and produce the compound:

adenosylcobalamin biosynthesis from cobyrinate a,c-diamide I , adenosylcobalamin biosynthesis from cobyrinate a,c-diamide II , adenosylcobalamin salvage from cobinamide I , adenosylcobalamin salvage from cobinamide II :
adenosyl-cobinamide phosphate + GTP + H+ ↔ adenosylcobinamide-GDP + diphosphate

anaerobic energy metabolism (invertebrates, cytosol) , gluconeogenesis III :
oxaloacetate + GTP ← CO2 + phosphoenolpyruvate + GDP

TCA cycle III (animals) :
succinate[mitochondrial lumen] + GTP[mitochondrial lumen] + coenzyme A[mitochondrial lumen] ↔ succinyl-CoA[mitochondrial lumen] + GDP[mitochondrial lumen] + phosphate[mitochondrial lumen]

In Reactions of unknown directionality:

Not in pathways:
P1,P4-bis(5'-guanosyl) tetraphosphate + H2O = GTP + GMP + 2 H+
a tRNA uridine34 + GTP + a 5,10-methylene-tetrahydrofolate + glycine + H2O = a tRNA containing 5-carboxymethylaminomethyluridine + GDP + a 7,8-dihydrofolate + phosphate
a tRNA 2-thiouridine34 + GTP + glycine + a 5,10-methylene-tetrahydrofolate + H2O = a tRNA containing 5-carboxymethylaminomethyl-2-thiouridine + GDP + a 7,8-dihydrofolate + phosphate
(deoxynucleotides)(m) + GTP + (deoxynucleotides)(n) = (deoxynucleotides)(n+m) + GMP + diphosphate
ATP + GTP = cyclic 3',5'-AMP-GMP + 2 diphosphate
ATP + GTP = pppGp(2'-5')A + diphosphate
cytidine + GTP = CMP + GDP + H+
pyruvate + GTP = phosphoenolpyruvate + GDP + H+
adenosylcobinamide + GTP = adenosyl-cobinamide phosphate + GDP + H+
p-tRNAHis + ATP + GTP = pppGp-tRNAHis + AMP + diphosphate
App-tRNAHis + GTP = pppGp-tRNAHis + AMP
5-hydroxy-L-lysine + GTP = (5R)-5-phosphonooxy-L-lysine + GDP + H+
uridine + GTP = UMP + GDP + H+
3-phospho-D-glycerate + GTP = 1,3-bisphospho-D-glycerate + GDP
2 GTP + H+ = P1,P4-bis(5'-guanosyl) tetraphosphate + diphosphate
GTP = cyclic-GMP + diphosphate


a purine ribonucleoside 5'-triphosphate + adenosylcobinamide = adenosyl-cobinamide phosphate + a purine ribonucleoside 5'-diphosphate + H+


a reduced flavodoxin + a ribonucleoside triphosphate = an oxidized flavodoxin + a deoxyribonucleoside triphosphate + H2O
a deoxyribonucleoside triphosphate + an oxidized thioredoxin + H2O = a ribonucleoside triphosphate + a reduced thioredoxin


a nucleoside triphosphate + AMP = a nucleoside diphosphate + ADP
a nucleoside triphosphate + RNA(n) = RNA(n+1) + diphosphate
RNA(n) + a nucleoside triphosphate = RNA(n+1) + diphosphate
a nucleoside triphosphate + an α-D-aldose 1-phosphate + H+ = a nucleoside diphosphate-hexose + diphosphate
a gentamicin + a nucleoside triphosphate = a 2-nucleotidylgentamicin + diphosphate


a nucleotide + a 2'-deoxynucleoside = a nucleoside + a 2'-deoxyribonucleoside 5'-monophosphate

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

Activator (Allosteric) of: UMP kinase [Serina95, Meyer08] , CTP synthase [Levitzki72, Comment 1] , thymidine kinase [Iwatsuki67, Chen78] , phosphoenolpyruvate carboxylase [Izui81] , AMP 5'-nucleotidase [Hunsucker01] , IMP 5'-nucleotidase [Spychala88]

Activator (Mechanism unknown) of: uracil phosphoribosyltransferase [Rasmussen86] , ornithine decarboxylase [Comment 2] , ornithine decarboxylase [Kanjee11] , amidophosphoribosyl transferase [Messenger79] , phytyl-P kinase [Ischebeck06]

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

Inhibitor (Competitive) of: guanosine kinase [Comment 3] , guanylate kinase [Oeschger66, Comment 4] , deoxyguanosine triphosphate triphosphohydrolase [KORNBERG58] , ITPase [Zheng05] , nucleoside diphosphate kinase [Roisin78, Comment 5] , cytidine 5'-monophosphate N-acetylneuraminate synthetase [RodriguezAparic92] , methionine adenosyltransferase [Comment 6] , dimethylallyl-diphosphate:AMP dimethylallyltransferase [Takei01]

Inhibitor (Noncompetitive) of: phosphoglucomutase [Duckworth73, Sanwal72] , adenylate cyclase [Yang83a]

Inhibitor (Allosteric) of: GTP cyclohydrolase [Basset02]

Inhibitor (Mechanism unknown) of: thiamine phosphate synthase [Kayama73, Kawasaki79] , methylenetetrahydrofolate dehydrogenase [Dev78] , m7GTP pyrophosphatase [Tchigvintsev13] , nucleoside diphosphate kinase [Roisin78, Comment 7] , phosphoribosylpyrophosphate amidotransferase [Satyanarayana71] , phosphoenolpyruvate carboxylase [Patel04] , ornithine carbamoyltransferase, catabolic [Ruepp95] , phosphoribosylpyrophosphate amidotransferase [Satyanarayana71] , glutamate dehydrogenase [Fang02] , homogalacturonan methyltransferase [Goubet99] , L-lactate dehydrogenase [Davies72] , AMP deaminase [Yabuki92] , inosine kinase [Combes89] , guanosine kinase [Combes89] , S-adenosylmethionine synthetase [Schroder97]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: McrBC restriction endonuclease


References

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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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