Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:13 UTC
HMDB IDHMDB01273
Secondary Accession NumbersNone
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
  1. 5'-GTP
  2. GTG
  3. GTP
  4. Guanosine 5'-(tetrahydrogen triphosphate)
  5. Guanosine 5'-triphosphate
  6. Guanosine 5'-triphosphorate
  7. Guanosine 5'-triphosphoric acid
  8. Guanosine mono(tetrahydrogen triphosphate) (ester)
  9. Guanosine Triphosphate
  10. H4gtp
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 IUPAC Name({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
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
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Ribonucleotides(KEGG)
  • guanosine 5'-phosphate(ChEBI)
  • purine ribonucleoside 5'-triphosphate(ChEBI)
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Glycosyl Compound
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Ribonucleoside Triphosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Folate biosynthesis
  • Component of Pyruvate metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • 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
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 area294.81ChemAxon
rotatable bond count8ChemAxon
refractivity97.24ChemAxon
polarizability39.81ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Neuron
  • Placenta
  • Platelet
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Citric Acid CycleSMP00057map00020
DNA Replication ForkSMP00477Not Available
GluconeogenesisSMP00128map00010
Pterine BiosynthesisSMP00005map00790
Purine MetabolismSMP00050map00230
Transcription/TranslationSMP00019Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified56.0 +/- 7.0 uMAdult (>18 years old)MaleNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified1.83 +/- 0.032 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected and Quantified1.59 +/- 1.42 uMAdult (>18 years old)BothRachialgia
Cerebrospinal Fluid (CSF)Detected and Quantified2.80 +/- 1.80 uMAdult (>18 years old)BothSubarachnoid hemorrhage
Cerebrospinal Fluid (CSF)Detected and Quantified2.08 +/- 1.91 uMAdult (>18 years old)BothEpilepsy
Cerebrospinal Fluid (CSF)Detected and Quantified1.30 +/- 1.23 uMAdult (>18 years old)BothCommentStroke
Cerebrospinal Fluid (CSF)Detected and Quantified1.92 +/- 1.53 uMAdult (>18 years old)BothNeuroinfection
Associated Disorders and Diseases
Disease References
Subarachnoid hemorrhage
  • 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
  • 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
  • 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
  • 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
  • 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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022527
KNApSAcK IDNot Available
Chemspider ID6569
KEGG Compound IDC00044
BioCyc IDGTP
BiGG ID33641
Wikipedia LinkGuanosine triphosphate
NuGOwiki LinkHMDB01273
Metagene LinkHMDB01273
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)Not Available
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 50 proteins. There are 569 proteins in total.

Enzymes

Gene Name:
PLD1
Uniprot ID:
Q13393
Gene Name:
ENTPD1
Uniprot ID:
P49961
Reactions
Guanosine triphosphate + Water unknown Guanosine diphosphate + Phosphoric aciddetails
Gene Name:
ENTPD3
Uniprot ID:
O75355
Reactions
Guanosine triphosphate + Water unknown Guanosine diphosphate + Phosphoric aciddetails
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Reactions
Guanosine triphosphate + Cytidine unknown Guanosine diphosphate + Cytidine monophosphatedetails
Guanosine triphosphate + Uridine unknown Guanosine diphosphate + Uridine 5'-monophosphatedetails
Gene Name:
NME4
Uniprot ID:
O00746
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
NME1
Uniprot ID:
P15531
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
NME2
Uniprot ID:
P22392
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
NME3
Uniprot ID:
Q13232
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
NME6
Uniprot ID:
O75414
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
FPGT
Uniprot ID:
O14772
Reactions
Guanosine triphosphate + Fucose 1-phosphate unknown Pyrophosphate + GDP-L-fucosedetails
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Reactions
Guanosine triphosphate + Water unknown Guanosine monophosphate + Pyrophosphatedetails
Gene Name:
GMPS
Uniprot ID:
P49915
Gene Name:
NUDT2
Uniprot ID:
P50583
Reactions
P(1),P(4)-bis(5'-guanosyl) tetraphosphate + Water unknown Guanosine triphosphate + Guanosine monophosphatedetails
Diguanosine tetraphosphate + Water unknown Guanosine triphosphate + Guanosine monophosphatedetails
Gene Name:
AK5
Uniprot ID:
Q9Y6K8
Gene Name:
CTPS1
Uniprot ID:
P17812
Gene Name:
ADCY7
Uniprot ID:
P51828
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY4
Uniprot ID:
Q8NFM4
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY6
Uniprot ID:
O43306
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY5
Uniprot ID:
O95622
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY8
Uniprot ID:
P40145
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY9
Uniprot ID:
O60503
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY3
Uniprot ID:
O60266
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY1
Uniprot ID:
Q08828
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
POLR3D
Uniprot ID:
P05423
Reactions
Guanosine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR2B
Uniprot ID:
P30876
Reactions
Guanosine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR2A
Uniprot ID:
P24928
Reactions
Guanosine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR1B
Uniprot ID:
Q9H9Y6
Reactions
Guanosine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR3G
Uniprot ID:
O15318
Reactions
Guanosine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR3B
Uniprot ID:
Q9NW08
Reactions
Guanosine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR1E
Uniprot ID:
Q9GZS1
Reactions
Guanosine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR3H
Uniprot ID:
Q9Y535
Reactions
Guanosine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR3K
Uniprot ID:
Q9Y2Y1
Reactions
Guanosine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
PKM
Uniprot ID:
P14618
Reactions
Guanosine triphosphate + Pyruvic acid unknown Guanosine diphosphate + Phosphoenolpyruvic aciddetails
Gene Name:
PKLR
Uniprot ID:
P30613
Reactions
Guanosine triphosphate + Pyruvic acid unknown Guanosine diphosphate + Phosphoenolpyruvic aciddetails
Gene Name:
ADSS
Uniprot ID:
P30520
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + N(6)-(1,2-dicarboxyethyl)AMPdetails
Gene Name:
ADSSL1
Uniprot ID:
Q8N142
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + N(6)-(1,2-dicarboxyethyl)AMPdetails
Gene Name:
SUCLG1
Uniprot ID:
P53597
Reactions
Guanosine triphosphate + Succinic acid + Coenzyme A unknown Guanosine diphosphate + Phosphoric acid + Succinyl-CoAdetails
Gene Name:
PCK2
Uniprot ID:
Q16822
Reactions
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + CO(2)details
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
Gene Name:
SUCLG2
Uniprot ID:
Q96I99
Reactions
Guanosine triphosphate + Succinic acid + Coenzyme A unknown Guanosine diphosphate + Phosphoric acid + Succinyl-CoAdetails
Gene Name:
PCK1
Uniprot ID:
P35558
Reactions
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + CO(2)details
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
Gene Name:
ADCY2
Uniprot ID:
Q08462
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
GCH1
Uniprot ID:
P30793
Reactions
Guanosine triphosphate + Water unknown Formic acid + 2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)-dihydropteridine triphosphatedetails
Guanosine triphosphate + Water unknown Formamidopyrimidine nucleoside triphosphatedetails
Gene Name:
SUCLA2
Uniprot ID:
Q9P2R7
Reactions
Guanosine triphosphate + Succinic acid + Coenzyme A unknown Guanosine diphosphate + Phosphoric acid + Succinyl-CoAdetails
Gene Name:
NPR2
Uniprot ID:
P20594
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails

Only showing the first 50 proteins. There are 569 proteins in total.