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Identification
YMDB IDYMDB00558
NameGTP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGuanosine triphosphate (GTP) is a guanine nucleotide containing three phosphate groups esterified to the sugar moiety. GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades.
Structure
Thumb
Synonyms
  • 5'-GTP
  • GTG
  • GTP
  • Guanosine 5'-(tetrahydrogen triphosphate)
  • Guanosine 5'-triphosphate
  • Guanosine 5'-triphosphorate
  • Guanosine 5'-triphosphoric acid
  • Guanosine Triphosphate
  • GUANOSINE-5'-triphosphATE
  • H4GTP
  • GUANOSINE-5'-triphosphoric acid
  • Guanosine triphosphoric acid
  • Guanosine mono(tetrahydrogen triphosphate) (ester)
  • Triphosphate, guanosine
CAS number86-01-1
WeightAverage: 523.1804
Monoisotopic: 522.990659781
InChI KeyXKMLYUALXHKNFT-UUOKFMHZSA-N
InChIInChI=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)/t3-,5-,6-,9-/m1/s1
IUPAC Name({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Nametriphosphate, guanosine
Chemical FormulaC10H16N5O14P3
SMILESNC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside triphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Hydroxypyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Monosaccharide
  • Phosphoric acid ester
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility10.4 g/LALOGPS
logP-0.63ALOGPS
logP-3.6ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)0.8ChemAxon
pKa (Strongest Basic)1.57ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area294.81 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity97.24 m³·mol⁻¹ChemAxon
Polarizability39.81 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
Riboflavin metabolismPW002443 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Folate biosynthesisec00790 Map00790
Purine metabolismec00230 Map00230
Pyrimidine metabolismec00240 Map00240
Riboflavin metabolismec00740 Map00740
SMPDB Reactions
Succinyl-CoA + phosphate + Guanosine diphosphateSuccinic acid + Coenzyme A + GTP
GTP + Inosinic acid + L-Aspartic acidGuanosine diphosphate + phosphate + Adenylsuccinic acid
Inosinic acid + L-Aspartic acid + GTPGuanosine diphosphate + phosphate + hydron + N6-(1,2-Dicarboxyethyl)-AMP
D-Mannose 1-phosphate + GTP + hydronPyrophosphate + Guanosine diphosphate mannose
GTP + waterFormic acid + hydron + 7,8-dihydroneopterin 3'-triphosphate
KEGG Reactions
Adenosine monophosphate + GTPADP + Guanosine diphosphate
GTP + Inosinic acid + L-Aspartic acidphosphate + hydron + Guanosine diphosphate + Adenylsuccinic acid
GTP + hydron + ADPP(1)-(5'-adenosyl),P(4)-(5'-guanosyl) tetraphosphate + phosphate
GTP + hydron + Guanosine diphosphatephosphate + P(1),P(4)-bis(5'-guanosyl) tetraphosphate
GTP + CytidineCytidine monophosphate + hydron + Guanosine diphosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Vozza, A., Blanco, E., Palmieri, L., Palmieri, F. (2004). "Identification of the mitochondrial GTP/GDP transporter in Saccharomyces cerevisiae." J Biol Chem 279:20850-20857.14998997
  • Gao, X. D., Kaigorodov, V., Jigami, Y. (1999). "YND1, a homologue of GDA1, encodes membrane-bound apyrase required for Golgi N- and O-glycosylation in Saccharomyces cerevisiae." J Biol Chem 274:21450-21456.10409709
Synthesis Reference:Stiller, Regine; Thiem, Joachim. Preparative enzymatic conversion of guanosine-5'-monophosphate to guanosine-5'-triphosphate. Synlett (1990), (11), 709-10.
External Links:
ResourceLink
CHEBI ID15996
HMDB IDHMDB01273
Pubchem Compound ID6830
Kegg IDC00044
ChemSpider ID6569
FOODB IDFDB022527
WikipediaGuanosine_triphosphate
BioCyc IDGTP

Enzymes

General function:
Involved in ATP adenylyltransferase activity
Specific function:
Ap4A phosphorylase catabolizes Ap4N nucleotides (where N is A,C,G or U). Additionally this enzyme catalyzes the conversion of adenosine-5-phosphosulfate (AMPs) plus Pi to ADP plus sulfate, the exchange of NDP and phosphate and the synthesis of Ap4A from AMPs plus ATP
Gene Name:
APA1
Uniprot ID:
P16550
Molecular weight:
36492.19922
Reactions
ADP + ATP → phosphate + P(1),P(4)-bis(5'-adenosyl) tetraphosphate.
ADP + sulfate → phosphate + adenylyl sulfate.
Adenylylsulfate + ATP → P(1),P(4)-bis(5'-adenosyl)tetraphosphate + sulfate.
General function:
Involved in adenylosuccinate synthase activity
Specific function:
Plays an important role in the de novo pathway and in the salvage pathway of purine nucleotide biosynthesis. Catalyzes the first commited step in the biosynthesis of AMP from IMP
Gene Name:
ADE12
Uniprot ID:
P80210
Molecular weight:
48279.10156
Reactions
GTP + IMP + L-aspartate → GDP + phosphate + N(6)-(1,2-dicarboxyethyl)-AMP.
General function:
Involved in catalytic activity
Specific function:
ATP + succinate + CoA = ADP + phosphate + succinyl-CoA
Gene Name:
LSC1
Uniprot ID:
P53598
Molecular weight:
35032.19922
Reactions
ATP + succinate + CoA → ADP + phosphate + succinyl-CoA.
General function:
Involved in catalytic activity
Specific function:
ATP + succinate + CoA = ADP + phosphate + succinyl-CoA
Gene Name:
LSC2
Uniprot ID:
P53312
Molecular weight:
46900.30078
Reactions
ATP + succinate + CoA → ADP + phosphate + succinyl-CoA.
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of phosphoanhydride bonds of nucleoside tri- and di-phosphates. Has equal high activity toward ADP/ATP, GDP/GTP, and UDP/UTP and approximately 50% less toward CDP/CTP and thiamine pyrophosphate. Has no activity toward GMP. Required for Golgi glycosylation and cell wall integrity. Together with CDC55, required for adenovirus E4orf4 (early region 4 open reading frame 4) induced toxicity, the apyrase activity is not required for this function. Plays a role in sphingolipid synthesis
Gene Name:
YND1
Uniprot ID:
P40009
Molecular weight:
71851.20313
Reactions
ATP + 2 H(2)O → AMP + 2 phosphate.
General function:
Involved in ATP binding
Specific function:
Catalyzes the conversion of uridine into UMP and cytidine into CMP in the pyrimidine salvage pathway
Gene Name:
URK1
Uniprot ID:
P27515
Molecular weight:
56295.5
Reactions
ATP + uridine → ADP + UMP.
ATP + cytidine → ADP + CMP.
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate. Required for repair of UV radiation- and etoposide-induced DNA damage
Gene Name:
YNK1
Uniprot ID:
P36010
Molecular weight:
17166.59961
Reactions
ATP + nucleoside diphosphate → ADP + nucleoside triphosphate.
General function:
Involved in ATP binding
Specific function:
RAR (regulation of autonomous replication) is a protein whose activity increases the mitotic stability of plasmids
Gene Name:
ERG12
Uniprot ID:
P07277
Molecular weight:
48458.89844
Reactions
ATP + (R)-mevalonate → ADP + (R)-5-phosphomevalonate.
General function:
Involved in ATP binding
Specific function:
This small ubiquitous enzyme is essential for maintenance and cell growth
Gene Name:
ADK2
Uniprot ID:
P26364
Molecular weight:
25193.69922
Reactions
ATP + AMP → 2 ADP.
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Small ubiquitous enzyme involved in energy metabolism and nucleotide synthesis that is essential for maintenance and cell growth. Functions both in the cytoplasm and mitochondrion intermembrane space
Gene Name:
ADK1
Uniprot ID:
P07170
Molecular weight:
24254.5
Reactions
ATP + AMP → 2 ADP.
General function:
Involved in ATP adenylyltransferase activity
Specific function:
Sustains the catabolism of Np-4-N' nucleotides, rather than their synthesis
Gene Name:
APA2
Uniprot ID:
P22108
Molecular weight:
36840.5
Reactions
ADP + ATP → phosphate + P(1),P(4)-bis(5'-adenosyl) tetraphosphate.
General function:
Involved in GTP cyclohydrolase II activity
Specific function:
Catalyzes the conversion of GTP to 2,5-diamino-6- ribosylamino-4(3H)-pyrimidinone 5'-phosphate (DARP), formate and pyrophosphate
Gene Name:
RIB1
Uniprot ID:
P38066
Molecular weight:
38331.60156
Reactions
GTP + 3 H(2)O → formate + 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine + diphosphate.
General function:
Involved in electron carrier activity
Specific function:
Participates as a hydrogen donor in redox reactions through the reversible oxidation of its active center dithiol to a disulfide, accompanied by the transfer of 2 electrons and 2 protons. It is involved in many cellular processes, including deoxyribonucleotide synthesis, repair of oxidatively damaged proteins, protein folding, sulfur metabolism, and redox homeostasis. Thioredoxin-dependent enzymes include phosphoadenosine-phosphosulfate reductase MET16, alkyl- hydroperoxide reductase DOT5, thioredoxin peroxidases TSA1 and TSA2, alkyl hydroperoxide reductase AHP1, and peroxiredoxin HYR1. Thioredoxin is also involved in protection against reducing stress. As part of the LMA1 complex, it is involved in the facilitation of vesicle fusion such as homotypic vacuole and ER- derived COPII vesicle fusion with the Golgi. This activity does not require the redox mechanism. Through its capacity to inactivate the stress response transcription factor YAP1 and its regulator the hydroperoxide stress sensor HYR1, it is involved in feedback regulation of stress response gene expression upon oxidative stress
Gene Name:
TRX2
Uniprot ID:
P22803
Molecular weight:
11203.7998
Reactions
General function:
Involved in electron carrier activity
Specific function:
Participates as a hydrogen donor in redox reactions through the reversible oxidation of its active center dithiol to a disulfide, accompanied by the transfer of 2 electrons and 2 protons. It is involved in many cellular processes, including deoxyribonucleotide synthesis, repair of oxidatively damaged proteins, protein folding, sulfur metabolism, and redox homeostasis. Thioredoxin-dependent enzymes include phosphoadenosine-phosphosulfate reductase MET16, alkyl- hydroperoxide reductase DOT5, thioredoxin peroxidases TSA1 and TSA2, alkyl hydroperoxide reductase AHP1, and peroxiredoxin HYR1. Thioredoxin is also involved in protection against reducing stress. As part of the LMA1 complex, it is involved in the facilitation of vesicle fusion such as homotypic vacuole and ER- derived COPII vesicle fusion with the Golgi. This activity does not require the redox mechanism
Gene Name:
TRX1
Uniprot ID:
P22217
Molecular weight:
11234.90039
Reactions
General function:
Involved in transferase activity
Specific function:
Involved in cell wall synthesis where it is required for glycosylation. Involved in cell cycle progression through cell- size checkpoint
Gene Name:
MPG1
Uniprot ID:
P41940
Molecular weight:
39565.60156
Reactions
GTP + alpha-D-mannose 1-phosphate → diphosphate + GDP-mannose.
General function:
Involved in GTP cyclohydrolase I activity
Specific function:
GTP + H(2)O = formate + 2-amino-4-hydroxy-6- (erythro-1,2,3-trihydroxypropyl)-dihydropteridine triphosphate
Gene Name:
FOL2
Uniprot ID:
P51601
Molecular weight:
27768.80078
Reactions
GTP + H(2)O → formate + 2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)-dihydropteridine triphosphate.
General function:
Involved in GTP binding
Specific function:
Microtubule-associated force-producing protein that participates mitochondrial fission. Fission of mitochondria occurs in many cell types and constitutes an important step in mitochondria morphology, which is balanced between fusion and fission. Functions antagonistically with FZO1
Gene Name:
DNM1
Uniprot ID:
P54861
Molecular weight:
84971.0
Reactions
GTP + H(2)O → GDP + phosphate.
General function:
Involved in mRNA guanylyltransferase activity
Specific function:
Second step of mRNA capping. Transfer of the GMP moiety of GTP to the 5'-end of RNA via an enzyme-GMP covalent reaction intermediate
Gene Name:
CEG1
Uniprot ID:
Q01159
Molecular weight:
52763.80078
Reactions
GTP + (5')pp-Pur-mRNA → diphosphate + G(5')ppp-Pur-mRNA.

Transporters

General function:
Involved in guanine nucleotide transmembrane transporte
Specific function:
Not Available
Gene Name:
YHM1
Uniprot ID:
P38988
Molecular weight:
33215.19922