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| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2020-02-26 21:23:04 UTC |
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| HMDB ID | HMDB0001201 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Guanosine diphosphate |
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| Description | Guanosine diphosphate, also known as 5'-GDP or 5'-diphosphate, guanosine, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. A guanine nucleotide containing two phosphate groups esterified to the sugar moiety. It is an ester of pyrophosphoric acid with the nucleoside guanosine. Guanosine diphosphate is a moderately basic compound (based on its pKa). Guanosine diphosphate exists in all living species, ranging from bacteria to humans. In humans, guanosine diphosphate is involved in intracellular signalling through adenosine receptor A2B and adenosine. Guanosine diphosphate is the product of GTP dephosphorylation by GTPases, e.g. the G-proteins that are involved in signal transduction. Outside of the human body, Guanosine diphosphate has been detected, but not quantified in, several different foods, such as common beans, kai-lans, fenugreeks, burdocks, and ryes. This could make guanosine diphosphate a potential biomarker for the consumption of these foods. Guanosine diphosphate consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase guanine. Guanosine 5'-(trihydrogen diphosphate). |
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| Structure | |
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| Synonyms | | Value | Source |
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| Guanosine 5'-diphosphate | ChEBI | | Guanosine 5'-diphosphoric acid | Generator | | Guanosine diphosphoric acid | Generator | | 5'-GDP | HMDB | | GDP | HMDB | | Guanosine 5'-(trihydrogen pyrophosphate) | HMDB | | Guanosine 5'-pyrophosphate | HMDB | | Guanosine mono(trihydrogen diphosphate) | HMDB | | Guanosine pyrophosphate | HMDB | | Guanosine-5'-diphosphate | HMDB | | Guanosine-diphosphate | HMDB | | PpG | HMDB | | 5'-Diphosphate, guanosine | HMDB | | Diphosphate, guanosine 5'-trihydrogen | HMDB | | Guanosine 5' diphosphate | HMDB | | Guanosine 5' trihydrogen diphosphate | HMDB | | 5'-Trihydrogen diphosphate, guanosine | HMDB | | Diphosphate, guanosine | HMDB | | Guanosine 5'-trihydrogen diphosphate | HMDB |
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| Chemical Formula | C10H15N5O11P2 |
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| Average Molecular Weight | 443.2005 |
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| Monoisotopic Molecular Weight | 443.024329371 |
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| IUPAC Name | [({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid |
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| Traditional Name | {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid |
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| CAS Registry Number | 146-91-8 |
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| SMILES | NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O |
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| InChI Identifier | InChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1 |
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| InChI Key | QGWNDRXFNXRZMB-UUOKFMHZSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate 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 diphosphates |
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| Alternative Parents | |
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| Substituents | - Purine ribonucleoside diphosphate
- Purine ribonucleoside monophosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-oxopurine
- Hypoxanthine
- Monosaccharide phosphate
- Organic pyrophosphate
- Pentose monosaccharide
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Monoalkyl phosphate
- Pyrimidone
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Alkyl phosphate
- Phosphoric acid ester
- Pyrimidine
- Vinylogous amide
- Tetrahydrofuran
- Azole
- Imidazole
- Heteroaromatic compound
- Secondary alcohol
- 1,2-diol
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Organooxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Alcohol
- Amine
- Organic oxygen compound
- Primary amine
- Organonitrogen 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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| Process | Naturally occurring process: |
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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-5930200000-bdc0893316c12636a495 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0229-6393250000-a57b7f18975223fa888c | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udl-0900600000-5c7173a5771dfefadc5e | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0udi-0900000000-d38af29994fa5108c331 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0udi-0900000000-3072d857dcc8a1b2cbaa | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-0kdi-5901100000-24a5c807e53370f01d0c | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0udi-0900000000-6399eaf97235815c4cb7 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0911300000-fcd49d8a5e9d3dc3f933 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-ded96f0f499982ac1ab0 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0900000000-ac93e95f54842f42e273 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f6x-0900800000-1ed1199fdace4d1b4d80 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zir-3900000000-b9aeef613c34fe99a48c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-f630c9237e72a76d3d63 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Extracellular
- Mitochondria
- Nucleus
- Golgi apparatus
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| Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
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| Tissue Locations | Not Available |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 15.0 +/- 2.0 uM | Adult (>18 years old) | Male | Normal | | details | | Blood | Detected and Quantified | 18.0 +/- 8.0 uM | Adult (>18 years old) | Both | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 1.86 +/- 0.027 uM | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.11 +/- 1.93 uM | Adult (>18 years old) | Both | Rachialgia | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 4.05 +/- 0.03 uM | Adult (>18 years old) | Both | Subarachnoid hemorrhage | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.99 +/- 1.32 uM | Adult (>18 years old) | Both | Epilepsy | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.55 +/- 1.62 uM | Adult (>18 years old) | Both | Stroke | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.59 +/- 1.77 uM | Adult (>18 years old) | Both | Neuroinfection | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Rachialgia |
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- 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 ]
| | Subarachnoid hemorrhage |
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- 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 |
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- 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 |
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- 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 |
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- 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 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | DB04315 |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | FDB030875 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 8630 |
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| KEGG Compound ID | C00035 |
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| BioCyc ID | Not Available |
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| BiGG ID | 33599 |
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| Wikipedia Link | Guanosine diphosphate |
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| METLIN ID | 6077 |
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| PubChem Compound | 8977 |
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| PDB ID | Not Available |
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| ChEBI ID | 17552 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | GDP |
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| References |
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| Synthesis Reference | Edlin, Gordon; Donini, P. Synthesis of guanosine 5'-diphosphate, 2'-(or 3'-) diphosphate, and related nucleotides in a variety of physiological conditions. Journal of Biological Chemistry (1971), 246(13), 4371-3. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
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