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Showing Compound Guanosine triphosphate (FDB022527)

Record Information
Version1.0
Creation date2011-09-21 00:15:24 UTC
Update date2020-09-17 15:40:25 UTC
Primary IDFDB022527
Secondary Accession Numbers
  • FDB030898
Chemical Information
FooDB NameGuanosine triphosphate
DescriptionGuanosine triphosphate, also known as 5'-GTP or H4GTP, 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. Thus, a GTP-bound tubulin serves as a cap at the tip of microtubule to protect from depolymerization; and, once the GTP is hydrolyzed, the microtubule begins to depolymerize and shrink rapidly. Guanosine triphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Guanosine triphosphate exists in all living species, ranging from bacteria to humans. In humans, guanosine triphosphate is involved in intracellular signalling through adenosine receptor A2B and adenosine. Guanosine-5'-triphosphate (GTP) is a purine nucleoside triphosphate. Outside of the human body, Guanosine triphosphate has been detected, but not quantified in, several different foods, such as mandarin orange (clementine, tangerine), coconuts, new zealand spinachs, sweet marjorams, and pepper (capsicum). This could make guanosine triphosphate a potential biomarker for the consumption of these foods. Cyclic guanosine triphosphate (cGTP) helps cyclic adenosine monophosphate (cAMP) activate cyclic nucleotide-gated ion channels in the olfactory system. It also has the role of a source of energy or an activator of substrates in metabolic reactions, like that of ATP, but more specific. It is used as a source of energy for protein synthesis and gluconeogenesis. For instance, a GTP molecule is generated by one of the enzymes in the citric acid cycle. GTP is also used as an energy source for the translocation of the ribosome towards the 3' end of the mRNA.During microtubule polymerization, each heterodimer formed by an alpha and a beta tubulin molecule carries two GTP molecules, and the GTP is hydrolyzed to GDP when the tubulin dimers are added to the plus end of the growing microtubule. The importing of these proteins plays an important role in several pathways regulated within the mitochondria organelle, such as converting oxaloacetate to phosphoenolpyruvate (PEP) in gluconeogenesis. GTP is involved in energy transfer within the cell.
CAS Number86-01-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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, guanosineMeSH, HMDB
Guanosine 5'-(tetrahydrogen triate)HMDB
Guanosine 5'-triateChEBI
Guanosine 5'-triic acidGenerator
Guanosine 5'-triorateHMDB
Guanosine 5'-trioric acidChEBI
Guanosine mono(tetrahydrogen triate) (ester)HMDB
Guanosine triateChEBI
Guanosine triic acidGenerator
Guanosine Triphosphatehmdb
GUANOSINE-5'-triATEChEBI
GUANOSINE-5'-triic acidGenerator
H4gtphmdb
Predicted Properties
PropertyValueSource
Water Solubility10.4 g/LALOGPS
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
Chemical FormulaC10H16N5O14P3
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight523.1804
Monoisotopic Molecular Weight522.990659781
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGuanosine triphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056v-8895330000-0a8a2d408be3cbe00023Spectrum
Predicted GC-MSGuanosine triphosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zos-8469026000-e08a35d5d35a9e63303cSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006t-0000970000-ed775d45b7d4c3b969df2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-0000920000-eea0cfe4824f5aee7e4a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-0900000000-895098906ea44c18ea432012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-1910300000-cbc290b8c193beb6665f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0910760000-0149aa219d4b60fa61f42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-1910300000-8315c93064efa4da6b1b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-1910300000-2664d57dfe06bffb291e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0100090000-b5bdb718aeaf9666be2a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-4910000000-13c0865e4dfdc30cae732021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0911220000-75ec8e10f63e3aae4b1f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-2b6055d302734ab3eecf2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-936551c9f8ce17b0cbfd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-0730090000-511cdeecbbfb6b7c86152016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zir-4930000000-cc969f818e5f659cd09c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-dff84bbb768f44c2c74b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900020000-66587b5a3e1149d9032f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900010000-2351199532a3a62427742021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0901000000-7daab2908ef3ebe15a5a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000190000-a7b3d2c63ee2ad144d4d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fi0-9742370000-3cb9d3e33126e947b5dd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200100000-29fc63b8efb32dd43b522021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID6569
ChEMBL IDNot Available
KEGG Compound IDC00044
Pubchem Compound ID6830
Pubchem Substance IDNot Available
ChEBI ID15996
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01273
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33641
KNApSAcK IDNot Available
HET IDGTP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGuanosine triphosphate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Rho-related GTP-binding protein RhoURHOUQ7L0Q8
Guanine nucleotide-binding protein G(s) subunit alpha isoforms shortGNASP63092
Guanine nucleotide-binding protein G(q) subunit alphaGNAQP50148
Uridine-cytidine kinase-like 1UCKL1Q9NWZ5
Rho guanine nucleotide exchange factor 1ARHGEF1Q92888
VinexinSORBS3O60504
Guanine nucleotide-binding protein subunit alpha-11GNA11P29992
Guanine nucleotide-binding protein G(t) subunit alpha-1GNAT1P11488
Lysophosphatidic acid receptor 2LPAR2Q9HBW0
Protein RCC2RCC2Q9P258
Protein very KINDKNDC1Q76NI1
DNA-directed RNA polymerase III subunit RPC4POLR3DP05423
DNA-directed RNA polymerase, mitochondrialPOLRMTO00411
DNA-directed RNA polymerase I subunit RPA2POLR1BQ9H9Y6
DNA-directed RNA polymerase III subunit RPC7POLR3GO15318
DNA-directed RNA polymerase III subunit RPC2POLR3BQ9NW08
DNA-directed RNA polymerase I subunit RPA49POLR1EQ9GZS1
DNA-directed RNA polymerase III subunit RPC8POLR3HQ9Y535
DNA-directed RNA polymerase III subunit RPC1POLR3AO14802
DNA-directed RNA polymerase I subunit RPA1POLR1AO95602
Zinc ribbon domain containing 1ZNRD1Q2L6J2
DNA-directed RNA polymerases I and III subunit RPAC2POLR1DQ9Y2S0
DNA-directed RNA polymeraseDKFZp686D10173Q7Z3R8
DNA-directed RNA polymerase III subunit RPC7-likePOLR3GLQ9BT43
POLR1C proteinPOLR1CQ96HT3
Leucine-rich repeat serine/threonine-protein kinase 2LRRK2Q5S007
Mitochondrial Rho GTPase 1RHOT1Q8IXI2
NineinNINQ8N4C6
Pathways
NameSMPDB LinkKEGG Link
Citric Acid CycleSMP00057 map00020
DNA Replication ForkSMP00477 Not Available
GluconeogenesisSMP00128 map00010
Pterine BiosynthesisSMP00005 map00790
Purine MetabolismSMP00050 map00230
Transcription/TranslationSMP00019 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference