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MetaCyc Compound: GTP

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

Superclasses: a nucleic acid componenta nucleotidea nucleoside triphosphatea ribonucleoside triphosphatea purine ribonucleoside 5'-triphosphate
a nucleic acid componenta nucleotidea purine nucleotidea purine ribonucleotidea purine ribonucleoside 5'-triphosphate
a nucleic acid componenta nucleotidea ribonucleotidea purine ribonucleotidea purine ribonucleoside 5'-triphosphate
a nucleic acid componenta nucleotidea ribonucleotidea ribonucleoside triphosphatea purine ribonucleoside 5'-triphosphate
a nucleic acid component
an organic heterocyclic compoundan organic heterobicyclic compounda purinea purine nucleotidea purine ribonucleotidea purine ribonucleoside 5'-triphosphate
an organic heterocyclic compoundan organonitrogen heterocyclic compounda purinea purine nucleotidea purine ribonucleotidea purine ribonucleoside 5'-triphosphate

Chemical Formula: C10H12N5O14P3

Molecular Weight: 519.15 Daltons

Monoisotopic Molecular Weight: 522.990659779 Daltons

GTP compound structure

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


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 Formation (ΔfG in kcal/mol): -553.3185Inferred 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 , tetrahydromonapterin biosynthesis :
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+

bis(guanylyl molybdenum cofactor) biosynthesis :
2 GTP + bis(molybdenum cofactor) + 2 H+bis(guanylyl molybdopterin cofactor) + 2 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 :
L-glutamate + GTP + oxidized coenzyme F420-0 → GDP + oxidized coenzyme F420-1 + phosphate + H+
L-glutamate + GTP + oxidized coenzyme F420-1 → GDP + oxidized coenzyme F420-2 + 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 :
α-D-glucopyranose 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

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

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

guanylyl molybdenum cofactor biosynthesis :
GTP + MoO2-molybdopterin cofactor + 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 + 2 H+ → a 5'-(5'-triphosphoguanosine)-purine-[mRNA] + diphosphate

oxidized GTP and dGTP detoxification :
GTP + 2 hydroxyl radical → 8-oxo-GTP + H2O

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 2-thiouridine34 in tRNA + a 5,10-methylene-tetrahydrofolate + ammonium + GTP + H2O → a 5-aminomethyl-2-thiouridine in tRNA + a 7,8-dihydrofolate + GDP + phosphate

Reactions known to produce the compound:

guanosine ribonucleotides de novo biosynthesis :

ppGpp biosynthesis :
pppGpp + H2O → GTP + diphosphate + H+

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

Not in pathways:
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 + GTP + coenzyme A ↔ succinyl-CoA + GDP + phosphate

In Reactions of unknown directionality:

Not in pathways:
P1,P4-bis(5'-guanosyl) tetraphosphate + H2O = GTP + GMP + 2 H+
a uridine in tRNA + GTP + taurine + a 5,10-methylene-tetrahydrofolate + an oxidized unknown electron acceptor + H2O = a 5-taurinomethyluridine in tRNA + GDP + a 7,8-dihydrofolate + an reduced unknown electron acceptor + phosphate + 2 H+
a uridine34 in tRNA + GTP + a 5,10-methylene-tetrahydrofolate + glycine + an oxidized unknown electron acceptor + H2O = a 5-carboxymethylaminomethyluridine in tRNA + GDP + a 7,8-dihydrofolate + an reduced unknown electron acceptor + phosphate + 2 H+
GTP + netilmicin = netilmycin 2''-phosphate + GDP + H+
GTP + sisomicin = sisomicin 2''-phosphate + GDP + H+
GTP + amikacin = amikacin 2''-phosphate + GDP + H+
GTP + arbekacin = arbekacin 2''-phosphate + GDP + H+
GTP + dibekacin = dibekacin 2''-phosphate + GDP + H+
GTP + tobramycin = tobramycin 2''-phosphate + GDP + H+
GTP + kanamycin B = kanamycin B 2''-phosphate + GDP + H+
GTP + kanamycin A = kanamycin A 2''-phosphate + GDP + H+
GTP + a gentamicin = a gentamicin 2''-phosphate + GDP + H+
GTP + gentamicin A = gentamicin A (2'')-phosphate + GDP + H+
a 2-thiouridine34 in tRNA + GTP + glycine + a 5,10-methylene-tetrahydrofolate + H2O = a 5-carboxymethylaminomethyl-2-thiouridine in tRNA + GDP + a 7,8-dihydrofolate + phosphate
(deoxynucleotides)(m) + GTP + (deoxynucleotides)(n) = (deoxynucleotides)(n+m) + GMP + diphosphate
ATP + GTP = cyclic Gp(2'-5')Ap(3'-5') + 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+

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

Activator (Allosteric) of: thymidine kinase [Iwatsuki67, Chen78], UMP kinase [Serina95, Meyer08], CTP synthase [Levitzki72, Comment 1], phosphoenolpyruvate carboxylase [Izui81], AMP 5'-nucleotidase [Hunsucker01], IMP 5'-nucleotidase [Spychala88] Activator (Mechanism unknown) of: ornithine decarboxylase [Comment 2], ornithine decarboxylase [Kanjee11], uracil phosphoribosyltransferase [Rasmussen86], 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], nucleoside diphosphate kinase [Roisin78, Comment 4], guanylate kinase [Oeschger66, Comment 5], deoxyguanosine triphosphate triphosphohydrolase [KORNBERG58], ITPase [Zheng05], cytidine 5'-monophosphate N-acetylneuraminate synthetase [RodriguezAparic92], methionine adenosyltransferase [Comment 6], dimethylallyl-diphosphate:AMP dimethylallyltransferase [Takei01] Inhibitor (Noncompetitive) of: phosphoglucomutase [Duckworth73, Sanwal72], adenylate cyclase [Yang83] Inhibitor (Allosteric) of: GTP cyclohydrolase [Basset02] Inhibitor (Mechanism unknown) of: pyruvate kinase [Waygood74], thiamine phosphate synthase [Kayama73, Kawasaki79], methylenetetrahydrofolate dehydrogenase [Dev78], nucleoside diphosphate kinase [Roisin78, Comment 7], m7GTP pyrophosphatase [Tchigvintsev13], 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

This compound has been characterized as an alternative substrate of the following enzymes: thiamine monophosphate phosphatase, AMP kinase, xanthosine triphosphate pyrophosphatase, arabinose kinase, dTMP kinase, N-acetylhexosamine kinase, dTDP kinase, succinyl-CoA synthetase, fructokinase, 1-phosphofructokinase, ATP:adenosylcobinamide phosphotransferase, adenylate cyclase, folylpoly-γ-glutamate synthetase, glycerate 2-kinase, pantothenate kinase, fructokinase, ATP synthase, [protein-PII] uridylyltransferase, phosphoribosylamidoimidazole-succinocarboxamide synthetase, acetate kinase, acetate kinase, 5,10-methylene-tetrahydrofolate:L-glutamate γ-ligase (ADP-forming), phosphatidylinositol-5-phosphate 4-kinase, 5-oxo-L-prolinase, N-citryl-spermidine:spermidine ligase, phosphoenolpyruvate phosphatase, cob(I)yrinic acid a,c-diamide adenosyltransferase, thymidine kinase, propionyl-CoA synthase, tetrahydrosarcinapterin synthase, adenylate kinase, tetraacyldisaccharide 4'-kinase, fructokinase, hydroxymethylpyrimidine kinase, RNA 3'-terminal phosphate cyclase, phosphoenolpyruvate phosphatase, deoxyguanosine triphosphate triphosphohydrolase, guanylate kinase, NAD kinase, nucleoside di- and triphosphate hydrolase, AMP kinase, dAMP kinase, tRNAMet cytidine acetyltransferase, fructokinase, 3,4-dihydroxybenzoyl-citryl-spermidine:spermidine ligase, 3-sulfinopropionyl-CoA synthetase, CMP kinase, O-phosphoseryl-tRNAsec kinase, ATPase, D-tagatose-6-phosphate kinase


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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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