Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:15:24 UTC |
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Update date | 2020-09-17 15:40:25 UTC |
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Primary ID | FDB022527 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Guanosine triphosphate |
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Description | Guanosine 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. |
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CAS Number | 86-01-1 |
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Structure | |
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Synonyms | Synonym | Source |
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5'-GTP | ChEBI | Guanosine 5'-triphosphate | ChEBI | Guanosine 5'-triphosphoric acid | ChEBI | GUANOSINE-5'-triphosphATE | ChEBI | H4GTP | ChEBI | GUANOSINE-5'-triphosphoric acid | Generator | Guanosine triphosphoric acid | Generator | GTG | HMDB | GTP | HMDB | Guanosine 5'-(tetrahydrogen triphosphate) | HMDB | Guanosine 5'-triphosphorate | HMDB | Guanosine mono(tetrahydrogen triphosphate) (ester) | HMDB | Triphosphate, guanosine | MeSH, HMDB | Guanosine 5'-(tetrahydrogen triate) | HMDB | Guanosine 5'-triate | ChEBI | Guanosine 5'-triic acid | Generator | Guanosine 5'-triorate | HMDB | Guanosine 5'-trioric acid | ChEBI | Guanosine mono(tetrahydrogen triate) (ester) | HMDB | Guanosine triate | ChEBI | Guanosine triic acid | Generator | Guanosine Triphosphate | hmdb | GUANOSINE-5'-triATE | ChEBI | GUANOSINE-5'-triic acid | Generator | H4gtp | hmdb |
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Predicted Properties | |
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Chemical Formula | C10H16N5O14P3 |
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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 |
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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 |
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InChI Key | XKMLYUALXHKNFT-UUOKFMHZSA-N |
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Isomeric 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 |
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Average Molecular Weight | 523.1804 |
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Monoisotopic Molecular Weight | 522.990659781 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Purine nucleotides |
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Sub Class | Purine ribonucleotides |
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Direct Parent | Purine ribonucleoside triphosphates |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Guanosine triphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-056v-8895330000-0a8a2d408be3cbe00023 | Spectrum | Predicted GC-MS | Guanosine triphosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0zos-8469026000-e08a35d5d35a9e63303c | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-006t-0000970000-ed775d45b7d4c3b969df | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0002-0000920000-eea0cfe4824f5aee7e4a | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-0900000000-895098906ea44c18ea43 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0a4i-1910300000-cbc290b8c193beb6665f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-05fr-0910760000-0149aa219d4b60fa61f4 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0a4i-1910300000-8315c93064efa4da6b1b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0a4i-1910300000-2664d57dfe06bffb291e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0100090000-b5bdb718aeaf9666be2a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0a6r-4910000000-13c0865e4dfdc30cae73 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0911220000-75ec8e10f63e3aae4b1f | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-2b6055d302734ab3eecf | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0900000000-936551c9f8ce17b0cbfd | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0fk9-0730090000-511cdeecbbfb6b7c8615 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zir-4930000000-cc969f818e5f659cd09c | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9300000000-dff84bbb768f44c2c74b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900020000-66587b5a3e1149d9032f | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900010000-2351199532a3a6242774 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0901000000-7daab2908ef3ebe15a5a | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0000190000-a7b3d2c63ee2ad144d4d | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fi0-9742370000-3cb9d3e33126e947b5dd | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200100000-29fc63b8efb32dd43b52 | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 6569 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00044 |
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Pubchem Compound ID | 6830 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15996 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB01273 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 33641 |
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KNApSAcK ID | Not Available |
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HET ID | GTP |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Guanosine triphosphate |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Rho-related GTP-binding protein RhoU | RHOU | Q7L0Q8 | Guanine nucleotide-binding protein G(s) subunit alpha isoforms short | GNAS | P63092 | Guanine nucleotide-binding protein G(q) subunit alpha | GNAQ | P50148 | Uridine-cytidine kinase-like 1 | UCKL1 | Q9NWZ5 | Rho guanine nucleotide exchange factor 1 | ARHGEF1 | Q92888 | Vinexin | SORBS3 | O60504 | Guanine nucleotide-binding protein subunit alpha-11 | GNA11 | P29992 | Guanine nucleotide-binding protein G(t) subunit alpha-1 | GNAT1 | P11488 | Lysophosphatidic acid receptor 2 | LPAR2 | Q9HBW0 | Protein RCC2 | RCC2 | Q9P258 | Protein very KIND | KNDC1 | Q76NI1 | DNA-directed RNA polymerase III subunit RPC4 | POLR3D | P05423 | DNA-directed RNA polymerase, mitochondrial | POLRMT | O00411 | DNA-directed RNA polymerase I subunit RPA2 | POLR1B | Q9H9Y6 | DNA-directed RNA polymerase III subunit RPC7 | POLR3G | O15318 | DNA-directed RNA polymerase III subunit RPC2 | POLR3B | Q9NW08 | DNA-directed RNA polymerase I subunit RPA49 | POLR1E | Q9GZS1 | DNA-directed RNA polymerase III subunit RPC8 | POLR3H | Q9Y535 | DNA-directed RNA polymerase III subunit RPC1 | POLR3A | O14802 | DNA-directed RNA polymerase I subunit RPA1 | POLR1A | O95602 | Zinc ribbon domain containing 1 | ZNRD1 | Q2L6J2 | DNA-directed RNA polymerases I and III subunit RPAC2 | POLR1D | Q9Y2S0 | DNA-directed RNA polymerase | DKFZp686D10173 | Q7Z3R8 | DNA-directed RNA polymerase III subunit RPC7-like | POLR3GL | Q9BT43 | POLR1C protein | POLR1C | Q96HT3 | Leucine-rich repeat serine/threonine-protein kinase 2 | LRRK2 | Q5S007 | Mitochondrial Rho GTPase 1 | RHOT1 | Q8IXI2 | Ninein | NIN | Q8N4C6 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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