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Showing metabocard for Guanosine diphosphate (BMDB0001201)
| Record Information | |||||||||||||||||||||||||||||||||||||||||
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| Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2016-09-30 22:42:31 UTC | ||||||||||||||||||||||||||||||||||||||||
| Update Date | 2020-05-21 16:29:08 UTC | ||||||||||||||||||||||||||||||||||||||||
| BMDB ID | BMDB0001201 | ||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Metabolite Identification | |||||||||||||||||||||||||||||||||||||||||
| Common Name | Guanosine diphosphate | ||||||||||||||||||||||||||||||||||||||||
| Description | Guanosine diphosphate, also known as Guanosine diphosphate or GDP, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. Guanosine diphosphate is possibly soluble (in water) and a moderately basic compound (based on its pKa). Guanosine diphosphate exists in all living species, ranging from bacteria to humans. In cattle, guanosine diphosphate is involved in a couple of metabolic pathways, which include the intracellular signalling through adenosine receptor A2A and adenosine pathway and the intracellular signalling through adenosine receptor A2B and adenosine pathway. | ||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||
| Synonyms |
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| Chemical Formula | C10H15N5O11P2 | ||||||||||||||||||||||||||||||||||||||||
| Average Molecular Weight | 443.2005 | ||||||||||||||||||||||||||||||||||||||||
| Monoisotopic Molecular Weight | 443.024329371 | ||||||||||||||||||||||||||||||||||||||||
| IUPAC Name | Not Available | ||||||||||||||||||||||||||||||||||||||||
| Traditional Name | Not Available | ||||||||||||||||||||||||||||||||||||||||
| CAS Registry Number | 146-91-8 | ||||||||||||||||||||||||||||||||||||||||
| SMILES | Not Available | ||||||||||||||||||||||||||||||||||||||||
| 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 | ||||||||||||||||||||||||||||||||||||||||
| InChI Key | QGWNDRXFNXRZMB-UUOKFMHZSA-N | ||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||
| 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. | ||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||
| Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||
| Class | Purine nucleotides | ||||||||||||||||||||||||||||||||||||||||
| Sub Class | Purine ribonucleotides | ||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Purine ribonucleoside diphosphates | ||||||||||||||||||||||||||||||||||||||||
| Alternative Parents |
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| Substituents |
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| Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Ontology | |||||||||||||||||||||||||||||||||||||||||
| Status | Expected but not Quantified | ||||||||||||||||||||||||||||||||||||||||
| Origin |
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| Biofunction | Not Available | ||||||||||||||||||||||||||||||||||||||||
| Application | Not Available | ||||||||||||||||||||||||||||||||||||||||
| Cellular locations |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||
| State | Solid | ||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Predicted Properties | Not Available | ||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||
| Spectra |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||
| Cellular Locations |
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| Biospecimen Locations | Not Available | ||||||||||||||||||||||||||||||||||||||||
| Pathways |
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| Normal Concentrations | |||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||
| Abnormal Concentrations | |||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||
| External Links | |||||||||||||||||||||||||||||||||||||||||
| HMDB ID | HMDB0001201 | ||||||||||||||||||||||||||||||||||||||||
| DrugBank ID | DB04315 | ||||||||||||||||||||||||||||||||||||||||
| Phenol Explorer Compound ID | Not Available | ||||||||||||||||||||||||||||||||||||||||
| FooDB ID | FDB030875 | ||||||||||||||||||||||||||||||||||||||||
| KNApSAcK ID | Not Available | ||||||||||||||||||||||||||||||||||||||||
| Chemspider ID | 8630 | ||||||||||||||||||||||||||||||||||||||||
| KEGG Compound ID | C00035 | ||||||||||||||||||||||||||||||||||||||||
| BioCyc ID | GDP | ||||||||||||||||||||||||||||||||||||||||
| BiGG ID | 33599 | ||||||||||||||||||||||||||||||||||||||||
| Wikipedia Link | Guanosine diphosphate | ||||||||||||||||||||||||||||||||||||||||
| METLIN ID | 6077 | ||||||||||||||||||||||||||||||||||||||||
| PubChem Compound | 8977 | ||||||||||||||||||||||||||||||||||||||||
| PDB ID | Not Available | ||||||||||||||||||||||||||||||||||||||||
| ChEBI ID | 17552 | ||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||
| 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. | ||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||
| General References | Not Available | ||||||||||||||||||||||||||||||||||||||||
Enzymes
- General function:
- Not Available
- Specific function:
- Canalicular ectonucleoside NTPDase responsible for the main hepatic NTPDase activity. Ectonucleoside NTPDases catalyze the hydrolysis of gamma- and beta-phosphate residues of nucleotides, playing a central role in concentration of extracellular nucleotides. Has activity toward ATP, ADP, UTP and UDP, but not toward AMP (By similarity).
- Gene Name:
- ENTPD8
- Uniprot ID:
- A0JND9
- Molecular weight:
- 53240.0
Reactions
| Guanosine triphosphate + Water → Guanosine diphosphate + Hydrogen phosphate | details |
- General function:
- Nucleotide transport and metabolism
- Specific function:
- Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate (By similarity).
- Gene Name:
- NME7
- Uniprot ID:
- Q5E9Y9
- Molecular weight:
- 42599.0
Reactions
| Adenosine triphosphate + Guanosine diphosphate → ADP + Guanosine triphosphate | details |
- General function:
- Nucleotide transport and metabolism
- Specific function:
- Component of the purine nucleotide cycle (PNC), which interconverts IMP and AMP to regulate the nucleotide levels in various tissues, and which contributes to glycolysis and ammoniagenesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP.
- Gene Name:
- ADSS1
- Uniprot ID:
- A5PJR4
- Molecular weight:
- 50134.0
Reactions
| Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Hydrogen phosphate + Adenylsuccinic acid | details |
- General function:
- Nucleotide transport and metabolism
- Specific function:
- Plays an important role in the de novo pathway and in the salvage pathway of purine nucleotide biosynthesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP.
- Gene Name:
- ADSS2
- Uniprot ID:
- A7MBG0
- Molecular weight:
- 50156.0
Reactions
| Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Hydrogen phosphate + Adenylsuccinic acid | details |
- General function:
- Energy production and conversion
- Specific function:
- Regulates cataplerosis and anaplerosis, the processes that control the levels of metabolic intermediates in the citric acid cycle. At low glucose levels, it catalyzes the cataplerotic conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle. At high glucose levels, it catalyzes the anaplerotic conversion of phosphoenolpyruvate to oxaloacetate.
- Gene Name:
- PCK1
- Uniprot ID:
- Q8HYZ4
- Molecular weight:
- 69353.0
Reactions
| Guanosine triphosphate + Oxalacetic acid → Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxide | details |
- General function:
- Energy production and conversion
- Specific function:
- Succinyl-CoA synthetase functions in the citric acid cycle (TCA), coupling the hydrolysis of succinyl-CoA to the synthesis of either ATP or GTP and thus represents the only step of substrate-level phosphorylation in the TCA. The alpha subunit of the enzyme binds the substrates coenzyme A and phosphate, while succinate binding and specificity for either ATP or GTP is provided by different beta subunits.
- Gene Name:
- SUCLG1
- Uniprot ID:
- Q58DR8
- Molecular weight:
- 36167.0
Reactions
| Succinyl-CoA + Hydrogen phosphate + Guanosine diphosphate → Succinic acid + Coenzyme A + Guanosine triphosphate | details |
- General function:
- Energy production and conversion
- Specific function:
- GTP-specific succinyl-CoA synthetase functions in the citric acid cycle (TCA), coupling the hydrolysis of succinyl-CoA to the synthesis of GTP and thus represents the only step of substrate-level phosphorylation in the TCA. The beta subunit provides nucleotide specificity of the enzyme and binds the substrate succinate, while the binding sites for coenzyme A and phosphate are found in the alpha subunit.
- Gene Name:
- SUCLG2
- Uniprot ID:
- Q3MHX5
- Molecular weight:
- 46691.0
Reactions
| Succinyl-CoA + Hydrogen phosphate + Guanosine diphosphate → Succinic acid + Coenzyme A + Guanosine triphosphate | details |
- General function:
- Nucleotide transport and metabolism
- Specific function:
- Catalyzes the phosphorylation of GMP to GDP. Essential enzyme for recycling GMP and indirectly, cyclic GMP (cGMP) (PubMed:8243671, PubMed:29515371, PubMed:7911663). Involved in the cGMP metabolism in photoreceptors (PubMed:29515371, PubMed:8243671).
- Gene Name:
- GUK1
- Uniprot ID:
- P46195
- Molecular weight:
- 21910.0
Reactions
| Adenosine triphosphate + Guanosine monophosphate → ADP + Guanosine diphosphate | details |
- General function:
- Not Available
- Specific function:
- Uridine diphosphatase (UDPase) that promotes protein N-glycosylation and ATP level regulation. UDP hydrolysis promotes protein N-glycosylation and folding in the endoplasmic reticulum, as well as elevated ATP consumption in the cytosol via an ATP hydrolysis cycle. Together with CMPK1 and AK1, constitutes an ATP hydrolysis cycle that converts ATP to AMP and results in a compensatory increase in aerobic glycolysis. The nucleotide hydrolyzing preference is GDP > IDP > UDP, but not any other nucleoside di-, mono- or triphosphates, nor thiamine pyrophosphate. Plays a key role in the AKT1-PTEN signaling pathway by promoting glycolysis in proliferating cells in response to phosphoinositide 3-kinase (PI3K) signaling (By similarity).
- Gene Name:
- ENTPD5
- Uniprot ID:
- E1BPW0
- Molecular weight:
- 47888.0
Reactions
| Guanosine diphosphate + Water → Guanosine monophosphate + Hydrogen phosphate | details |
| Guanosine triphosphate + Water → Guanosine diphosphate + Hydrogen phosphate | details |
- General function:
- Not Available
- Specific function:
- Functions as a guanine nucleotide exchange factor (GEF), which activates Rap and Ras family of small GTPases by exchanging bound GDP for free GTP in a cAMP-dependent manner. Serves as a link between cell surface receptors and Rap/Ras GTPases in intracellular signaling cascades. Acts also as an effector for Rap1 by direct association with Rap1-GTP thereby leading to the amplification of Rap1-mediated signaling. Shows weak activity on HRAS. It is controversial whether RAPGEF2 binds cAMP and cGMP or not. Its binding to ligand-activated beta-1 adrenergic receptor ADRB1 leads to the Ras activation through the G(s)-alpha signaling pathway. Involved in the cAMP-induced Ras and Erk1/2 signaling pathway that leads to sustained inhibition of long term melanogenesis by reducing dendrite extension and melanin synthesis. Provides also inhibitory signals for cell proliferation of melanoma cells and promotes their apoptosis in a cAMP-independent nanner. Regulates cAMP-induced neuritogenesis by mediating the Rap1/B-Raf/ERK signaling through a pathway that is independent on both PKA and RAPGEF3/RAPGEF4. Involved in neuron migration and in the formation of the major forebrain fiber connections forming the corpus callosum, the anterior commissure and the hippocampal commissure during brain development. Involved in neuronal growth factor (NGF)-induced sustained activation of Rap1 at late endosomes and in brain-derived neurotrophic factor (BDNF)-induced axon outgrowth of hippocampal neurons. Plays a role in the regulation of embryonic blood vessel formation and in the establishment of basal junction integrity and endothelial barrier function. May be involved in the regulation of the vascular endothelial growth factor receptor KDR and cadherin CDH5 expression at allantois endothelial cell-cell junctions (By similarity). Binds to cAMP.
- Gene Name:
- RAPGEF2
- Uniprot ID:
- F1MSG6
- Molecular weight:
- 165144.0
Reactions
| Cyclic AMP + Rap guanine nucleotide exchange factor 3 + Guanosine triphosphate + Ras-related protein Rap-1A → Guanosine diphosphate + Ras-related protein Rap-1A | details |
| GTPase HRas with GDP + Guanosine triphosphate → GTPase HRas with GTP + Guanosine diphosphate | details |
- General function:
- Not Available
- Specific function:
- Acts as guanine nucleotide exchange factor (GEF) for CDC42. Promotes formation of GPHN clusters (By similarity).
- Gene Name:
- ARHGEF9
- Uniprot ID:
- Q58DL7
- Molecular weight:
- 65980.0
Reactions
| Cell division control protein 42 homolog with GDP + Guanosine triphosphate → Cell division control protein 42 homolog with GTP + Guanosine diphosphate | details |
- General function:
- Not Available
- Specific function:
- Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides.
- Gene Name:
- RRM1
- Uniprot ID:
- F1MSF1
- Molecular weight:
- 89991.0
Reactions
| dGDP + Thioredoxin Disulfide + Water → Guanosine diphosphate + Thioredoxin | details |