Guanosine diphosphate (PAMDB000296)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 1/22/2018 11:54:54 AM | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Metabolite ID | PAMDB000296 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Guanosine diphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description: | Guanosine 5'-(trihydrogen diphosphate). A guanine nucleotide containing two phosphate groups esterified to the sugar moiety. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase guanine. GDP is the product of GTP dephosphorylation by GTPases, e.g. the G-proteins that are involved in signal transduction. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C10H15N5O11P2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight: | 443.2005 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight: | 443.024329371 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | QGWNDRXFNXRZMB-UUOKFMHZSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | 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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 146-91-8 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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]phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | GDP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Taxonomy Description | This compound 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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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Guanosine diphosphate + Reduced Thioredoxin > dGDP + Water + Oxidized Thioredoxin Guanosine diphosphate + glutaredoxin > dGDP + glutaredoxin + Water Adenosine triphosphate + Guanosine diphosphate <> ADP + Guanosine triphosphate Adenosine triphosphate + Guanosine triphosphate + Water + Sulfate > Adenosine phosphosulfate + Guanosine diphosphate + Phosphate + Pyrophosphate Adenosine triphosphate + Guanosine diphosphate > Adenosine monophosphate + Hydrogen ion + Guanosine 3',5'-bis(diphosphate) P1,P4-Bis(5'-guanosyl) tetraphosphate + Water >2 Guanosine diphosphate +2 Hydrogen ion Adenosine monophosphate + Guanosine triphosphate <> ADP + Guanosine diphosphate Guanosine triphosphate + Water > Guanosine diphosphate + Hydrogen ion + Phosphate Guanosine diphosphate + Hydrogen ion + D-Mannose 1-phosphate > Guanosine diphosphate mannose + Phosphate Guanosine diphosphate mannose + Water > Guanosine diphosphate + Hydrogen ion + D-Mannose Cytidine + Guanosine triphosphate > Cytidine monophosphate + Guanosine diphosphate + Hydrogen ion Guanosine triphosphate + Uridine > Guanosine diphosphate + Hydrogen ion + Uridine 5'-monophosphate Adenosine triphosphate + Guanosine monophosphate <> ADP + Guanosine diphosphate Water + Guanosine 3',5'-bis(diphosphate) <> Guanosine diphosphate + Pyrophosphate L-Aspartic acid + Guanosine triphosphate + Inosinic acid <> Adenylsuccinic acid + Guanosine diphosphate +2 Hydrogen ion + Phosphate Guanosine triphosphate + Pyruvic acid <> Guanosine diphosphate + Phosphoenolpyruvic acid RNA + Phosphate <> RNA + Guanosine diphosphate Guanosine triphosphate + Cytidine <> Guanosine diphosphate + Cytidine monophosphate Guanosine triphosphate + Uridine <> Guanosine diphosphate + Uridine 5'-monophosphate Guanosine triphosphate + Inosinic acid + L-Aspartic acid <> Guanosine diphosphate + Phosphate + Adenylsuccinic acid dGDP + Thioredoxin disulfide + Water <> Guanosine diphosphate + Thioredoxin Adenosyl cobinamide + Guanosine triphosphate <> Adenosyl cobinamide phosphate + Guanosine diphosphate More...L-Aspartic acid + Inosinic acid + Guanosine triphosphate > Hydrogen ion + adenylo-succinate + Phosphate + Guanosine diphosphate GDP-α-D-glucose + Water > Hydrogen ion + b-D-Glucose + Guanosine diphosphate Adenosine triphosphate + Guanosine diphosphate > Adenosine monophosphate + Guanosine 3',5'-bis(diphosphate) Guanosine diphosphate + Water > Hydrogen ion + Guanosine monophosphate + Phosphate Guanosine 3',5'-bis(diphosphate) + Water > Hydrogen ion + Pyrophosphate + Guanosine diphosphate Guanosine diphosphate mannose + Water > Guanosine diphosphate + D-Mannose Guanosine triphosphate + Water > Guanosine diphosphate + Inorganic phosphate Adenosine triphosphate + Guanosine triphosphate + Adenosyl cobinamide <> Adenosyl cobinamide phosphate + ADP + Guanosine diphosphate Succinyl-CoA + Phosphate + Guanosine diphosphate + Succinyl-CoA <> Succinic acid + Coenzyme A + Guanosine triphosphate Guanosine triphosphate + Inosinic acid + L-Aspartic acid + L-Aspartic acid > Guanosine diphosphate + Phosphate + N(6)-(1,2-dicarboxyethyl)AMP Inosinic acid + L-Aspartic acid + Guanosine triphosphate + L-Aspartic acid > Guanosine diphosphate + Phosphate +2 Hydrogen ion + N(6)-(1,2-dicarboxyethyl)AMP + Adenylsuccinic acid Guanosine monophosphate + Adenosine triphosphate > Adenosine diphosphate + Guanosine diphosphate + ADP Guanosine diphosphate + Adenosine triphosphate > Adenosine diphosphate + Guanosine triphosphate + ADP Guanosine diphosphate + reduced thioredoxin > oxidized thioredoxin + Water + dGDP + dGDP Guanosine diphosphate + a reduced NrdH glutaredoxin-like protein > Water + an oxidized NrdH glutaredoxin-like protein + dGDP + dGDP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in oxidation-reduction process
- Specific function:
- Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. R1 contains the binding sites for both substrates and allosteric effectors and carries out the actual reduction of the ribonucleotide. It also provides redox- active cysteines
- Gene Name:
- nrdA
- Locus Tag:
- PA1156
- Molecular weight:
- 107.1 kDa
Reactions
2'-deoxyribonucleoside diphosphate + thioredoxin disulfide + H(2)O = ribonucleoside diphosphate + thioredoxin. |
- General function:
- Involved in RNA binding
- Specific function:
- Involved in mRNA degradation. Hydrolyzes single-stranded polyribonucleotides processively in the 3'- to 5'-direction
- Gene Name:
- pnp
- Locus Tag:
- PA4740
- Molecular weight:
- 75.4 kDa
Reactions
RNA(n+1) + phosphate = RNA(n) + a nucleoside diphosphate. |
- General function:
- Involved in bis(5'-nucleosyl)-tetraphosphatase (symmetrical) activity
- Specific function:
- Hydrolyzes diadenosine 5',5'''-P1,P4-tetraphosphate to yield ADP
- Gene Name:
- apaH
- Locus Tag:
- PA0590
- Molecular weight:
- 32 kDa
Reactions
P(1),P(4)-bis(5'-adenosyl) tetraphosphate + H(2)O = 2 ADP. |
- General function:
- Involved in nucleoside diphosphate kinase activity
- 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
- Gene Name:
- ndk
- Locus Tag:
- PA3807
- Molecular weight:
- 15.6 kDa
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate. |
- General function:
- Involved in adenylosuccinate synthase activity
- Specific function:
- Plays an important role in the de novo pathway of purine nucleotide biosynthesis. Catalyzes the first commited step in the biosynthesis of AMP from IMP
- Gene Name:
- purA
- Locus Tag:
- PA4938
- Molecular weight:
- 46.8 kDa
Reactions
GTP + IMP + L-aspartate = GDP + phosphate + N(6)-(1,2-dicarboxyethyl)-AMP. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- ATP + pyruvate = ADP + phosphoenolpyruvate
- Gene Name:
- pykF
- Locus Tag:
- PA1498
- Molecular weight:
- 51.5 kDa
Reactions
ATP + pyruvate = ADP + phosphoenolpyruvate. |
- General function:
- Involved in nucleotide binding
- Specific function:
- ATP-dependent phosphorylation of adenosylcobinamide and adds GMP to adenosylcobinamide phosphate
- Gene Name:
- cobU
- Locus Tag:
- PA1279
- Molecular weight:
- 36.5 kDa
Reactions
ATP or GTP + adenosylcobinamide = adenosylcobinamide phosphate + ADP or GDP. |
GTP + adenosylcobinamide phosphate = diphosphate + adenosylcobinamide-GDP. |
- General function:
- Involved in amino acid binding
- Specific function:
- In eubacteria ppGpp (guanosine 3'-diphosphate 5-' diphosphate) is a mediator of the stringent response that coordinates a variety of cellular activities in response to changes in nutritional abundance. This enzyme catalyzes the formation of pppGpp which is then hydrolyzed to form ppGpp
- Gene Name:
- relA
- Locus Tag:
- PA0934
- Molecular weight:
- 83.8 kDa
Reactions
ATP + GTP = AMP + guanosine 3'-diphosphate 5'-triphosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- In eubacteria ppGpp (guanosine 3'-diphosphate 5-' diphosphate) is a mediator of the stringent response that coordinates a variety of cellular activities in response to changes in nutritional abundance. This enzyme catalyzes both the synthesis and degradation of ppGpp. The second messengers ppGpp and c-di-GMP together control biofilm formation in response to translational stress; ppGpp represses biofilm formation while c- di-GMP induces it
- Gene Name:
- spoT
- Locus Tag:
- PA5338
- Molecular weight:
- 78.9 kDa
Reactions
ATP + GTP = AMP + guanosine 3'-diphosphate 5'-triphosphate. |
Guanosine 3',5'-bis(diphosphate) + H(2)O = guanosine 5'-diphosphate + diphosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- ATP + sulfate = diphosphate + adenylyl sulfate
- Gene Name:
- cysD
- Locus Tag:
- PA4443
- Molecular weight:
- 35.5 kDa
Reactions
ATP + sulfate = diphosphate + adenylyl sulfate. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- ATP + pyruvate = ADP + phosphoenolpyruvate
- Gene Name:
- pykA
- Locus Tag:
- PA4329
- Molecular weight:
- 52.3 kDa
Reactions
ATP + pyruvate = ADP + phosphoenolpyruvate. |
- General function:
- Involved in GTPase activity
- Specific function:
- May be the GTPase, regulating ATP sulfurylase activity
- Gene Name:
- cysN
- Locus Tag:
- PA4442
- Molecular weight:
- 69.3 kDa
Reactions
ATP + sulfate = diphosphate + adenylyl sulfate. |
- General function:
- Involved in nucleotidyltransferase activity
- Specific function:
- Involved in the biosynthesis of the capsular polysaccharide colanic acid
- Gene Name:
- manC
- Locus Tag:
- PA3551
- Molecular weight:
- 53.1 kDa
Reactions
GTP + alpha-D-mannose 1-phosphate = diphosphate + GDP-mannose. |
- General function:
- Involved in catalytic activity
- Specific function:
- 2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin
- Gene Name:
- nrdD
- Locus Tag:
- PA1920
- Molecular weight:
- 76.1 kDa
Reactions
2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin. |
- General function:
- Involved in protein binding
- Specific function:
- Essential for recycling GMP and indirectly, cGMP
- Gene Name:
- gmk
- Locus Tag:
- PA5336
- Molecular weight:
- 23.1 kDa
Reactions
ATP + GMP = ADP + GDP. |
- General function:
- Involved in ATP binding
- Specific function:
- Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. This small ubiquitous enzyme involved in the energy metabolism and nucleotide synthesis, is essential for maintenance and cell growth
- Gene Name:
- adk
- Locus Tag:
- PA3686
- Molecular weight:
- 23.1 kDa
Reactions
ATP + AMP = 2 ADP. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. R2 contains the tyrosyl radical required for catalysis
- Gene Name:
- nrdB
- Locus Tag:
- PA1155
- Molecular weight:
- 47.4 kDa
Reactions
2'-deoxyribonucleoside diphosphate + thioredoxin disulfide + H(2)O = ribonucleoside diphosphate + thioredoxin. |
- General function:
- Involved in electron carrier activity
- Specific function:
- Monothiol glutaredoxin involved in the biogenesis of iron-sulfur clusters (Probable)
- Gene Name:
- grxD
- Locus Tag:
- PA3533
- Molecular weight:
- 11.8 kDa
- General function:
- Involved in electron carrier activity
- Specific function:
- The disulfide bond functions as an electron carrier in the glutathione-dependent synthesis of deoxyribonucleotides by the enzyme ribonucleotide reductase. In addition, it is also involved in reducing some disulfides in a coupled system with glutathione reductase
- Gene Name:
- grxC
- Locus Tag:
- PA5129
- Molecular weight:
- 9.2 kDa
- General function:
- Involved in electron carrier activity
- Specific function:
- Participates in various redox reactions through the reversible oxidation of its active center dithiol to a disulfide and catalyzes dithiol-disulfide exchange reactions
- Gene Name:
- trxA
- Locus Tag:
- PA5240
- Molecular weight:
- 11.9 kDa
Transporters
- General function:
- Involved in nucleoside diphosphate kinase activity
- 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
- Gene Name:
- ndk
- Locus Tag:
- PA3807
- Molecular weight:
- 15.6 kDa
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate. |