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Record Information
Version1.0
Creation Date2016-09-30 22:43:27 UTC
Update Date2020-05-21 16:29:08 UTC
BMDB IDBMDB0001273
Secondary Accession Numbers
  • BMDB01273
Metabolite Identification
Common NameGuanosine triphosphate
DescriptionGuanosine triphosphate, also known as 5'-GTP or guanosine triphosphate, 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. Guanosine triphosphate is possibly soluble (in water) and a moderately basic compound (based on its pKa). Guanosine triphosphate exists in all living species, ranging from bacteria to humans. In cattle, guanosine triphosphate is involved in a couple of metabolic pathways, which include the intracellular signalling through adenosine receptor A2A and adenosine pathway and the intracellular signalling through adenosine receptor A2B and adenosine pathway.
Structure
Thumb
Synonyms
ValueSource
5'-GTPChEBI
Guanosine 5'-triphosphateChEBI
Guanosine 5'-triphosphoric acidChEBI
GUANOSINE-5'-triphosphATEChEBI
H4GTPChEBI
GUANOSINE-5'-triphosphoric acidGenerator
Guanosine triphosphoric acidGenerator
GTGHMDB
GTPHMDB
Guanosine 5'-(tetrahydrogen triphosphate)HMDB
Guanosine 5'-triphosphorateHMDB
Guanosine mono(tetrahydrogen triphosphate) (ester)HMDB
Triphosphate, guanosineHMDB
Chemical FormulaC10H16N5O14P3
Average Molecular Weight523.1804
Monoisotopic Molecular Weight522.990659781
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 Nametriphosphate, guanosine
CAS Registry Number86-01-1
SMILES
NC1=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
InChI Identifier
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)/t3-,5-,6-,9-/m1/s1
InChI KeyXKMLYUALXHKNFT-UUOKFMHZSA-N
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.63ALOGPS
logP-3.7ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056v-8895330000-0a8a2d408be3cbe00023View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0zos-8469026000-e08a35d5d35a9e63303cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006t-0000970000-ed775d45b7d4c3b969dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-0000920000-eea0cfe4824f5aee7e4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-0900000000-895098906ea44c18ea43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0911220000-75ec8e10f63e3aae4b1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-2b6055d302734ab3eecfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-936551c9f8ce17b0cbfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-0730090000-511cdeecbbfb6b7c8615View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zir-4930000000-cc969f818e5f659cd09cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-dff84bbb768f44c2c74bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • Neuron
  • Placenta
  • Platelet
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
NeuronExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001273
DrugBank IDDB04137
Phenol Explorer Compound IDNot Available
FooDB IDFDB022527
KNApSAcK IDC00007223
Chemspider ID6569
KEGG Compound IDC00044
BioCyc IDGTP
BiGG ID33641
Wikipedia LinkGuanosine triphosphate
METLIN ID6128
PubChem Compound6830
PDB IDNot Available
ChEBI ID15996
References
Synthesis ReferenceStiller, Regine; Thiem, Joachim. Preparative enzymatic conversion of guanosine-5'-monophosphate to guanosine-5'-triphosphate. Synlett (1990), (11), 709-10.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Signal transduction mechanisms
Specific function:
Mediates responses to nitric oxide (NO) by catalyzing the biosynthesis of the signaling molecule cGMP.
Gene Name:
GUCY1B1
Uniprot ID:
P16068
Molecular weight:
70502.0
Reactions
Guanosine triphosphate → Guanosine 2',3'-cyclic phosphate + Pyrophosphatedetails
Guanosine triphosphate → Cyclic GMPdetails
General function:
Not Available
Specific function:
Canalicular ectonucleoside NTPDase responsible for the main hepatic NTPDase activity. Ectonucleoside NTPDases catalyze the hydrolysis of gamma- and beta-phosphate residues of nucleotides, playing a central role in concentration of extracellular nucleotides. Has activity toward ATP, ADP, UTP and UDP, but not toward AMP (By similarity).
Gene Name:
ENTPD8
Uniprot ID:
A0JND9
Molecular weight:
53240.0
Reactions
Guanosine triphosphate + Water → Guanosine diphosphate + Hydrogen phosphatedetails
General function:
Nucleotide transport and metabolism
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 (By similarity).
Gene Name:
NME7
Uniprot ID:
Q5E9Y9
Molecular weight:
42599.0
Reactions
Adenosine triphosphate + Guanosine diphosphate → ADP + Guanosine triphosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Component of the purine nucleotide cycle (PNC), which interconverts IMP and AMP to regulate the nucleotide levels in various tissues, and which contributes to glycolysis and ammoniagenesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP.
Gene Name:
ADSS1
Uniprot ID:
A5PJR4
Molecular weight:
50134.0
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Hydrogen phosphate + Adenylsuccinic aciddetails
General function:
Nucleotide transport and metabolism
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q2KIC5
Molecular weight:
23061.0
Reactions
Guanosine triphosphate + Water → Guanosine monophosphate + Pyrophosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Plays an important role in the de novo pathway and in the salvage pathway of purine nucleotide biosynthesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP.
Gene Name:
ADSS2
Uniprot ID:
A7MBG0
Molecular weight:
50156.0
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Hydrogen phosphate + Adenylsuccinic aciddetails
General function:
Energy production and conversion
Specific function:
Regulates cataplerosis and anaplerosis, the processes that control the levels of metabolic intermediates in the citric acid cycle. At low glucose levels, it catalyzes the cataplerotic conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle. At high glucose levels, it catalyzes the anaplerotic conversion of phosphoenolpyruvate to oxaloacetate.
Gene Name:
PCK1
Uniprot ID:
Q8HYZ4
Molecular weight:
69353.0
Reactions
Guanosine triphosphate + Oxalacetic acid → Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
General function:
Energy production and conversion
Specific function:
Succinyl-CoA synthetase functions in the citric acid cycle (TCA), coupling the hydrolysis of succinyl-CoA to the synthesis of either ATP or GTP and thus represents the only step of substrate-level phosphorylation in the TCA. The alpha subunit of the enzyme binds the substrates coenzyme A and phosphate, while succinate binding and specificity for either ATP or GTP is provided by different beta subunits.
Gene Name:
SUCLG1
Uniprot ID:
Q58DR8
Molecular weight:
36167.0
Reactions
Succinyl-CoA + Hydrogen phosphate + Guanosine diphosphate → Succinic acid + Coenzyme A + Guanosine triphosphatedetails
General function:
Energy production and conversion
Specific function:
GTP-specific succinyl-CoA synthetase functions in the citric acid cycle (TCA), coupling the hydrolysis of succinyl-CoA to the synthesis of GTP and thus represents the only step of substrate-level phosphorylation in the TCA. The beta subunit provides nucleotide specificity of the enzyme and binds the substrate succinate, while the binding sites for coenzyme A and phosphate are found in the alpha subunit.
Gene Name:
SUCLG2
Uniprot ID:
Q3MHX5
Molecular weight:
46691.0
Reactions
Succinyl-CoA + Hydrogen phosphate + Guanosine diphosphate → Succinic acid + Coenzyme A + Guanosine triphosphatedetails
General function:
Signal transduction mechanisms
Specific function:
Not Available
Gene Name:
GUCY1A1
Uniprot ID:
P19687
Molecular weight:
77533.0
Reactions
Guanosine triphosphate → Guanosine 2',3'-cyclic phosphate + Pyrophosphatedetails
Guanosine triphosphate → Cyclic GMPdetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the formation of GDP-mannose, an essential precursor of glycan moieties of glycoproteins and glycolipids.
Gene Name:
GMPPB
Uniprot ID:
Q2YDJ9
Molecular weight:
39837.0
Reactions
Guanosine triphosphate + D-Mannose 1-phosphate → Guanosine diphosphate mannose + Pyrophosphatedetails
General function:
Involved in protein binding
Specific function:
Mediates tetrahydrobiopterin inhibition of GTP cyclohydrolase 1. This inhibition is reversed by L-phenylalanine (By similarity).
Gene Name:
GCHFR
Uniprot ID:
Q32L41
Molecular weight:
9557.0
Reactions
Guanosine triphosphate + Water → Formamidopyrimidine nucleoside triphosphate + Formic aciddetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
FPGT
Uniprot ID:
E1B9U5
Molecular weight:
67389.0
Reactions
Fucose 1-phosphate + Guanosine triphosphate → GDP-L-fucose + Pyrophosphatedetails
General function:
Not Available
Specific function:
Asymmetrically hydrolyzes Ap4A to yield AMP and ATP. Plays a major role in maintaining homeostasis.
Gene Name:
NUDT2
Uniprot ID:
Q29RJ1
Molecular weight:
16775.0
Reactions
Diguanosine tetraphosphate + Water → Guanosine triphosphate + Guanosine monophosphatedetails
General function:
Not Available
Specific function:
Uridine diphosphatase (UDPase) that promotes protein N-glycosylation and ATP level regulation. UDP hydrolysis promotes protein N-glycosylation and folding in the endoplasmic reticulum, as well as elevated ATP consumption in the cytosol via an ATP hydrolysis cycle. Together with CMPK1 and AK1, constitutes an ATP hydrolysis cycle that converts ATP to AMP and results in a compensatory increase in aerobic glycolysis. The nucleotide hydrolyzing preference is GDP > IDP > UDP, but not any other nucleoside di-, mono- or triphosphates, nor thiamine pyrophosphate. Plays a key role in the AKT1-PTEN signaling pathway by promoting glycolysis in proliferating cells in response to phosphoinositide 3-kinase (PI3K) signaling (By similarity).
Gene Name:
ENTPD5
Uniprot ID:
E1BPW0
Molecular weight:
47888.0
Reactions
Guanosine triphosphate + Water → Guanosine diphosphate + Hydrogen phosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
GCH1
Uniprot ID:
F1MZ14
Molecular weight:
27726.0
Reactions
Guanosine triphosphate + Water → Formamidopyrimidine nucleoside triphosphate + Formic aciddetails
General function:
Not Available
Specific function:
Functions as a guanine nucleotide exchange factor (GEF), which activates Rap and Ras family of small GTPases by exchanging bound GDP for free GTP in a cAMP-dependent manner. Serves as a link between cell surface receptors and Rap/Ras GTPases in intracellular signaling cascades. Acts also as an effector for Rap1 by direct association with Rap1-GTP thereby leading to the amplification of Rap1-mediated signaling. Shows weak activity on HRAS. It is controversial whether RAPGEF2 binds cAMP and cGMP or not. Its binding to ligand-activated beta-1 adrenergic receptor ADRB1 leads to the Ras activation through the G(s)-alpha signaling pathway. Involved in the cAMP-induced Ras and Erk1/2 signaling pathway that leads to sustained inhibition of long term melanogenesis by reducing dendrite extension and melanin synthesis. Provides also inhibitory signals for cell proliferation of melanoma cells and promotes their apoptosis in a cAMP-independent nanner. Regulates cAMP-induced neuritogenesis by mediating the Rap1/B-Raf/ERK signaling through a pathway that is independent on both PKA and RAPGEF3/RAPGEF4. Involved in neuron migration and in the formation of the major forebrain fiber connections forming the corpus callosum, the anterior commissure and the hippocampal commissure during brain development. Involved in neuronal growth factor (NGF)-induced sustained activation of Rap1 at late endosomes and in brain-derived neurotrophic factor (BDNF)-induced axon outgrowth of hippocampal neurons. Plays a role in the regulation of embryonic blood vessel formation and in the establishment of basal junction integrity and endothelial barrier function. May be involved in the regulation of the vascular endothelial growth factor receptor KDR and cadherin CDH5 expression at allantois endothelial cell-cell junctions (By similarity). Binds to cAMP.
Gene Name:
RAPGEF2
Uniprot ID:
F1MSG6
Molecular weight:
165144.0
Reactions
Cyclic AMP + Rap guanine nucleotide exchange factor 3 + Guanosine triphosphate + Ras-related protein Rap-1A → Guanosine diphosphate + Ras-related protein Rap-1Adetails
GTPase HRas with GDP + Guanosine triphosphate → GTPase HRas with GTP + Guanosine diphosphatedetails
General function:
Not Available
Specific function:
Acts as guanine nucleotide exchange factor (GEF) for CDC42. Promotes formation of GPHN clusters (By similarity).
Gene Name:
ARHGEF9
Uniprot ID:
Q58DL7
Molecular weight:
65980.0
Reactions
Cell division control protein 42 homolog with GDP + Guanosine triphosphate → Cell division control protein 42 homolog with GTP + Guanosine diphosphatedetails