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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-06-19 22:08:11 UTC
HMDB IDHMDB0001273
Secondary Accession Numbers
  • HMDB01273
Metabolite Identification
Common NameGuanosine triphosphate
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. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA.
Structure
Thumb
Synonyms
ValueSource
5'-GTPChEBI
Guanosine 5'-triphosphateChEBI
Guanosine 5'-triphosphoric acidChEBI
GUANOSINE-5'-triphosphATEChEBI
H4GTPChEBI
Guanosine triphosphoric acidGenerator
GUANOSINE-5'-triphosphoric acidGenerator
GTGHMDB
GTPHMDB
Guanosine 5'-(tetrahydrogen triphosphate)HMDB
Guanosine 5'-triphosphorateHMDB
Guanosine mono(tetrahydrogen triphosphate) (ester)HMDB
Triphosphate, guanosineMeSH
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
DescriptionThis compound 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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
  • Extracellular
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Locations
  • Neuron
  • Placenta
  • Platelet
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified56.0 +/- 7.0 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified1.83 +/- 0.032 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified1.59 +/- 1.42 uMAdult (>18 years old)BothRachialgia details
Cerebrospinal Fluid (CSF)Detected and Quantified2.80 +/- 1.80 uMAdult (>18 years old)BothSubarachnoid hemorrhage details
Cerebrospinal Fluid (CSF)Detected and Quantified2.08 +/- 1.91 uMAdult (>18 years old)BothEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified1.30 +/- 1.23 uMAdult (>18 years old)Both
Stroke
details
Cerebrospinal Fluid (CSF)Detected and Quantified1.92 +/- 1.53 uMAdult (>18 years old)BothNeuroinfection details
Associated Disorders and Diseases
Disease References
Subarachnoid hemorrhage
  1. Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
Epilepsy
  1. Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
Neuroinfection
  1. Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
Rachialgia
  1. Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
Stroke
  1. Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022527
KNApSAcK IDC00007223
Chemspider ID6569
KEGG Compound IDC00044
BioCyc IDGTP
BiGG ID33641
Wikipedia LinkGuanosine triphosphate
METLIN ID6128
PubChem Compound6830
PDB IDGTP
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)Download (PDF)
General References
  1. Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. [PubMed:8595732 ]
  2. Naylor EW, Ennis D, Davidson AG, Wong LT, Applegarth DA, Niederwieser A: Guanosine triphosphate cyclohydrolase I deficiency: early diagnosis by routine urine pteridine screening. Pediatrics. 1987 Mar;79(3):374-8. [PubMed:3822637 ]
  3. Iwanaga N, Yamamasu S, Tachibana D, Nishio J, Nakai Y, Shintaku H, Ishiko O: Activity of synthetic enzymes of tetrahydrobiopterin in the human placenta. Int J Mol Med. 2004 Jan;13(1):117-20. [PubMed:14654981 ]
  4. Lester HA, Steer ML, Levitzki A: Prostaglandin-stimulated GTP hydrolysis associated with activation of adenylate cyclase in human platelet membranes. Proc Natl Acad Sci U S A. 1982 Feb;79(3):719-23. [PubMed:6121325 ]
  5. Reichert LE Jr, Dattatreyamurty B: The follicle-stimulating hormone (FSH) receptor in testis: interaction with FSH, mechanism of signal transduction, and properties of the purified receptor. Biol Reprod. 1989 Jan;40(1):13-26. [PubMed:2493820 ]
  6. Schmidt VA, Scudder L, Devoe CE, Bernards A, Cupit LD, Bahou WF: IQGAP2 functions as a GTP-dependent effector protein in thrombin-induced platelet cytoskeletal reorganization. Blood. 2003 Apr 15;101(8):3021-8. Epub 2002 Dec 19. [PubMed:12515716 ]
  7. Chen Q, He Y, Yang K: Gene therapy for Parkinson's disease: progress and challenges. Curr Gene Ther. 2005 Feb;5(1):71-80. [PubMed:15638712 ]

Only showing the first 10 proteins. There are 569 proteins in total.

Enzymes

General function:
Involved in protein binding
Specific function:
Implicated as a critical step in numerous cellular pathways, including signal transduction, membrane trafficking, and the regulation of mitosis. May be involved in the regulation of perinuclear intravesicular membrane traffic (By similarity).
Gene Name:
PLD1
Uniprot ID:
Q13393
Molecular weight:
124183.135
General function:
Involved in hydrolase activity
Specific function:
In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:
ENTPD1
Uniprot ID:
P49961
Molecular weight:
58706.0
Reactions
Guanosine triphosphate + Water → Guanosine diphosphate + Phosphoric aciddetails
General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24
General function:
Involved in hydrolase activity
Specific function:
Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:
ENTPD3
Uniprot ID:
O75355
Molecular weight:
59104.76
Reactions
Guanosine triphosphate + Water → Guanosine diphosphate + Phosphoric aciddetails
General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Molecular weight:
22760.43
Reactions
Guanosine triphosphate + Cytidine → Guanosine diphosphate + Cytidine monophosphatedetails
Guanosine triphosphate + Uridine → Guanosine diphosphate + Uridine 5'-monophosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP (By similarity).
Gene Name:
NME4
Uniprot ID:
O00746
Molecular weight:
20658.45
Reactions
Adenosine triphosphate + Guanosine diphosphate → ADP + Guanosine triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. Possesses nucleoside-diphosphate kinase, serine/threonine-specific protein kinase, geranyl and farnesyl pyrophosphate kinase, histidine protein kinase and 3'-5' exonuclease activities. Involved in cell proliferation, differentiation and development, signal transduction, G protein-coupled receptor endocytosis, and gene expression. Required for neural development including neural patterning and cell fate determination.
Gene Name:
NME1
Uniprot ID:
P15531
Molecular weight:
17148.635
Reactions
Adenosine triphosphate + Guanosine diphosphate → ADP + Guanosine triphosphatedetails
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.
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Molecular weight:
42491.365
Reactions
Adenosine triphosphate + Guanosine diphosphate → ADP + Guanosine triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. Negatively regulates Rho activity by interacting with AKAP13/LBC. Acts as a transcriptional activator of the MYC gene; binds DNA non-specifically (PubMed:8392752). Exhibits histidine protein kinase activity.
Gene Name:
NME2
Uniprot ID:
P22392
Molecular weight:
30136.92
Reactions
Adenosine triphosphate + Guanosine diphosphate → ADP + Guanosine triphosphatedetails
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. Probably has a role in normal hematopoiesis by inhibition of granulocyte differentiation and induction of apoptosis.
Gene Name:
NME3
Uniprot ID:
Q13232
Molecular weight:
19014.85
Reactions
Adenosine triphosphate + Guanosine diphosphate → ADP + Guanosine triphosphatedetails

Only showing the first 10 proteins. There are 569 proteins in total.