Guanosine monophosphate (PAMDB000369)
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Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 1/22/2018 12:54:54 PM | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Metabolite ID | PAMDB000369 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Guanosine monophosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description: | Guanosine 5'-monophosphate. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C10H14N5O8P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight: | 363.2206 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight: | 363.057998961 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | RQFCJASXJCIDSX-UUOKFMHZSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 85-32-5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | guanylate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(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 monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Purine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Purine ribonucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Purine ribonucleoside monophosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 triphosphate + Water > Guanosine monophosphate + Hydrogen ion + Pyrophosphate Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate Guanosine monophosphate + Water > Guanosine + Phosphate Guanosine monophosphate + 2 Hydrogen ion + NADPH > Inosinic acid + NADP + Ammonium Adenosine triphosphate + Guanosine > ADP + Guanosine monophosphate + Hydrogen ion Cyclic GMP + Water > Guanosine monophosphate + Hydrogen ion Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole > Adenosylcobalamin + Guanosine monophosphate + Hydrogen ion Guanosine diphosphate mannose + Water > Guanosine monophosphate +2 Hydrogen ion + D-Mannose 1-phosphate Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + Pyrophosphate Adenosine triphosphate + Guanosine monophosphate <> ADP + Guanosine diphosphate Guanosine triphosphate + Water <> Guanosine monophosphate + Pyrophosphate Inosinic acid + Ammonia + NADP <> Guanosine monophosphate + NADPH + Hydrogen ion Adenosine triphosphate + Guanosine <> ADP + Guanosine monophosphate Adenosine triphosphate + Xanthylic acid + Ammonia <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate Adenosylcobalamin + Guanosine monophosphate <> Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole Adenosylcobinamide-GDP + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole > adenosylcobalamin 5'-phosphate + Guanosine monophosphate + Hydrogen ion Adenosine triphosphate + Xanthylic acid + Ammonia > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate More...Guanosine diphosphate + Water > Hydrogen ion + Guanosine monophosphate + Phosphate Inosinic acid + Ammonia + NADP > Guanosine monophosphate + NADPH Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole <> Guanosine monophosphate + Adenosylcobalamin + Adenosylcobalamin 5'-phosphate Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate Xanthylic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + L-Glutamic acid +2 Hydrogen ion + Guanosine monophosphate + L-Glutamate Guanosine monophosphate + Adenosine triphosphate > Adenosine diphosphate + Guanosine diphosphate + ADP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Sato, Katsuaki; Matsui, Hiroshi; Ei, Hitoshi; Takinami, Koichi. Guanosine-5'-monophosphate. Jpn. Kokai Tokkyo Koho (1979), 3 pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in GMP synthase (glutamine-hydrolyzing) activity
- Specific function:
- Catalyzes the synthesis of GMP from XMP
- Gene Name:
- guaA
- Locus Tag:
- PA3769
- Molecular weight:
- 58 kDa
Reactions
ATP + xanthosine 5'-phosphate + L-glutamine + H(2)O = AMP + diphosphate + GMP + L-glutamate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Nucleotidase with a broad substrate specificity as it can dephosphorylate various ribo- and deoxyribonucleoside 5'- monophosphates and ribonucleoside 3'-monophosphates with highest affinity to 3'-AMP. Also hydrolyzes polyphosphate (exopolyphosphatase activity) with the preference for short-chain- length substrates (P20-25). Might be involved in the regulation of dNTP and NTP pools, and in the turnover of 3'-mononucleotides produced by numerous intracellular RNases (T1, T2, and F) during the degradation of various RNAs. Also plays a significant physiological role in stress-response and is required for the survival of Pseudomonas aeruginosa in stationary growth phase
- Gene Name:
- surE
- Locus Tag:
- PA3625
- Molecular weight:
- 26.4 kDa
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
A 3'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
(Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate. |
- General function:
- Involved in acid phosphatase activity
- Specific function:
- Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
- Gene Name:
- aphA
- Locus Tag:
- PA1409
- Molecular weight:
- 38 kDa
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate. |
- General function:
- Involved in nucleoside-triphosphate diphosphatase activity
- Specific function:
- Specific function unknown
- Gene Name:
- mazG
- Locus Tag:
- PA0935
- Molecular weight:
- 31.2 kDa
Reactions
ATP + H(2)O = AMP + diphosphate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Hydrolyzes O6 atom-containing purine bases deoxyinosine triphosphate (dITP) and xanthosine triphosphate (XTP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) to nucleotide monophosphate and pyrophosphate. Probably excludes non- standard purines from DNA precursor pool, preventing thus incorporation into DNA and avoiding chromosomal lesions
- Gene Name:
- rdgB
- Locus Tag:
- PA0387
- Molecular weight:
- 21.2 kDa
Reactions
A nucleoside triphosphate + H(2)O = a nucleotide + diphosphate. |
- 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 adenine phosphoribosyltransferase activity
- Specific function:
- Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis
- Gene Name:
- apt
- Locus Tag:
- PA1543
- Molecular weight:
- 19.8 kDa
Reactions
AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Replication, recombination and repair
- Specific function:
- Involved in the GO system responsible for removing an oxidatively damaged form of guanine (7,8-dihydro-8-oxoguanine) from DNA and the nucleotide pool. 8-oxo-dGTP is inserted opposite dA and dC residues of template DNA with almost equal efficiency thus leading to A.T to G.C transversions. MutT specifically degrades 8-oxo-dGTP to the monophosphate
- Gene Name:
- mutT
- Locus Tag:
- PA4400
- Molecular weight:
- 34 kDa
Reactions
8-oxo-dGTP + H(2)O = 8-oxo-dGMP + diphosphate. |