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Guanosine triphosphate (PC000245)

Record Information
Version1.0
Creation date2015-10-09 22:29:25 UTC
Update date2017-01-19 02:36:17 UTC
FoodComEx IDPC000245
FoodDB RecordFDB022527
Chemical Information
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'-GTPhmdb
GTGhmdb
GTPHMDB
Guanosine 5'-(tetrahydrogen triate)HMDB
Guanosine 5'-(tetrahydrogen triphosphate)hmdb
Guanosine 5'-triateChEBI
Guanosine 5'-triic acidGenerator
Guanosine 5'-triorateHMDB
Guanosine 5'-trioric acidChEBI
Guanosine 5'-triphosphatehmdb
Guanosine 5'-triphosphoratehmdb
Guanosine 5'-triphosphoric acidhmdb
Guanosine mono(tetrahydrogen triate) (ester)HMDB
Guanosine mono(tetrahydrogen triphosphate) (ester)hmdb
Guanosine triateChEBI
Guanosine triic acidGenerator
Guanosine Triphosphatehmdb
GUANOSINE-5'-triATEChEBI
GUANOSINE-5'-triic acidGenerator
H4gtphmdb
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
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 10 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available