Guanosine 3'-diphosphate 5'-triphosphate (ECMDB20156) (M2MDB001003)
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 14:30:25 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 17:19:25 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Guanosine 3'-diphosphate 5'-triphosphate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Guanosine 3'-diphosphate 5'-triphosphate is a member of the chemical class known as Purine Ribonucleoside 3',5'-Bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. The hallmark of the stringent response is the accumulation of guanosine tetra- (ppGpp) and pentaphosphates (pppGpp), which probably bind RNA polymerase to regulate gene expression at certain promoters. (PMID 11282471) Guanosine 5'-triphosphate 3'-diphosphate (pppGpp) and guanosine 5'-diphosphate 3'-diphosphate (ppGpp) are specifically degraded by a manganese-dependent pyrophosphorylase present in spoT+ but not in spoT- strains of Escherichia coli, indicating that the enzyme is the spoT gene product. (PMID 365225) The kinetics of the GTP level during starvation suggests that GTP is a precursor of pppGpp. (PMID 793688) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C10H18N5O20P5 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 683.1402 Monoisotopic: 682.923320601 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | KCPMACXZAITQAX-UUOKFMHZSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C10H18N5O20P5/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(32-39(26,27)33-36(18,19)20)3(31-9)1-30-38(24,25)35-40(28,29)34-37(21,22)23/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H,28,29)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 38918-96-6 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | {[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})phosphoryl]oxy}phosphonic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | {hydroxy[(2R,3S,4R,5R)-4-hydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)-2-[({hydroxy[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphoryl}oxyphosphonic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | [H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])OP(O)(=O)OP(O)(O)=O | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Nucleosides, nucleotides, and analogues | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Purine nucleotides | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Purine ribonucleotides | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Purine ribonucleoside triphosphates | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -6 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine triphosphate + Guanosine triphosphate <> Adenosine monophosphate + Guanosine 3'-diphosphate 5'-triphosphate + Hydrogen ion Guanosine 3'-diphosphate 5'-triphosphate + Water > Guanosine triphosphate + Pyrophosphate Guanosine 3'-diphosphate 5'-triphosphate + Water <> Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate) Adenosine triphosphate + Guanosine triphosphate <> Adenosine monophosphate + Guanosine 3'-diphosphate 5'-triphosphate Guanosine 3'-diphosphate 5'-triphosphate + Water <> Guanosine 3',5'-bis(diphosphate) + Phosphate Guanosine triphosphate + Adenosine triphosphate > Guanosine 3'-diphosphate 5'-triphosphate + Adenosine monophosphate Water + Guanosine 3'-diphosphate 5'-triphosphate > Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate) Guanosine 3'-diphosphate 5'-triphosphate + Water > Hydrogen ion + Guanosine triphosphate + Pyrophosphate Guanosine 3'-diphosphate 5'-triphosphate + Water > Guanosine 3',5'-bis(diphosphate) + Inorganic phosphate Adenosine triphosphate + Guanosine triphosphate <> Adenosine monophosphate + Guanosine 3'-diphosphate 5'-triphosphate + Hydrogen ion Guanosine 3'-diphosphate 5'-triphosphate + Water <> Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate) Adenosine triphosphate + Guanosine triphosphate <> Adenosine monophosphate + Guanosine 3'-diphosphate 5'-triphosphate + Hydrogen ion Guanosine 3'-diphosphate 5'-triphosphate + Water <> Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Pathways: |
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EcoCyc Pathways: |
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Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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References: |
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Synthesis Reference: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in magnesium ion binding
- Specific function:
- Degradation of inorganic polyphosphates. Orthophosphate is released progressively from the ends of polyphosphate of circa 500 residues long, while chains of circa 15 residues compete poorly with polyphosphate as substrate
- Gene Name:
- ppx
- Uniprot ID:
- P0AFL6
- Molecular weight:
- 58136
Reactions
(Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate. |
- 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
- Uniprot ID:
- P0AG20
- Molecular weight:
- 83875
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
- Uniprot ID:
- P0AG24
- Molecular weight:
- 79342
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 guanosine-5'-triphosphate,3'-diphosphate diphosphatase activity
- Specific function:
- Conversion of pppGpp to ppGpp. Guanosine pentaphosphate (pppGpp) is a cytoplasmic signaling molecule which together with ppGpp controls the "stringent response", an adaptive process that allows bacteria to respond to amino acid starvation, resulting in the coordinated regulation of numerous cellular activities
- Gene Name:
- gppA
- Uniprot ID:
- P25552
- Molecular weight:
- 54871
Reactions
Guanosine 5'-triphosphate,3'-diphosphate + H(2)O = guanosine 3',5'-bis(diphosphate) + phosphate. |