Guanosine monophosphate (ECMDB01397) (M2MDB000369)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:51:38 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:11 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Formula: | C10H14N5O8P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 363.2206 Monoisotopic: 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 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 |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Predicted Properties |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 Guanosine monophosphate + Water <> Guanosine + Phosphate Adenosine triphosphate + Guanosine <> ADP + Guanosine monophosphate Guanosine monophosphate + Pyrophosphate <> Guanine + Phosphoribosyl pyrophosphate 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 Guanosine diphosphate mannose + Water > Hydrogen ion + Guanosine monophosphate + D-Mannose 1-phosphate Adenosylcobinamide-GDP + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole > adenosylcobalamin 5'-phosphate + Guanosine monophosphate + Hydrogen ion Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole Hydrogen ion + Adenosylcobalamin + Guanosine monophosphate Ammonia + Inosinic acid + NADP < Hydrogen ion + Guanosine monophosphate + NADPH Water + L-Glutamine + Xanthylic acid + Adenosine triphosphate > Hydrogen ion + L-Glutamate + Guanosine monophosphate + Pyrophosphate + Adenosine monophosphate Adenosine triphosphate + Xanthylic acid + Ammonia > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate Guanosine diphosphate + Water > Hydrogen ion + Guanosine monophosphate + Phosphate GMP-Lysine + Water > Guanosine monophosphate + N-alpha-acetyl lysine methyl ester More...GDP-cobinamide + alpha-ribazole > Cob(I)alamin + Guanosine monophosphate Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate Inosinic acid + Ammonia + NADP > Guanosine monophosphate + NADPH Adenosine triphosphate + Guanosine monophosphate > ADP + Guanosine diphosphate Guanosine diphosphate mannose + Water > Guanosine monophosphate + Alpha-D-mannose 1-phosphate 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 Guanine + Phosphoribosyl pyrophosphate > Pyrophosphate + Guanosine monophosphate Guanosine triphosphate + Water > Guanosine monophosphate + Hydrogen ion + Pyrophosphate Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + Pyrophosphate Guanosine triphosphate + Water > Guanosine monophosphate + Hydrogen ion + Pyrophosphate Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + Pyrophosphate Guanosine triphosphate + Water > Guanosine monophosphate + Hydrogen ion + Pyrophosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: |
|
Enzymes
- General function:
- Involved in GMP synthase (glutamine-hydrolyzing) activity
- Specific function:
- Catalyzes the synthesis of GMP from XMP
- Gene Name:
- guaA
- Uniprot ID:
- P04079
- Molecular weight:
- 58679
Reactions
ATP + xanthosine 5'-phosphate + L-glutamine + H(2)O = AMP + diphosphate + GMP + L-glutamate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
- Gene Name:
- ushA
- Uniprot ID:
- P07024
- Molecular weight:
- 60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate. |
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
- 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 E.coli in stationary growth phase
- Gene Name:
- surE
- Uniprot ID:
- P0A840
- Molecular weight:
- 26900
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 catalytic activity
- Specific function:
- Nucleotidase that shows high phosphatase activity toward three nucleoside 5'-monophosphates, UMP, dUMP, and dTMP, and very low activity against TDP, IMP, UDP, GMP, dGMP, AMP, dAMP, and 6- phosphogluconate. Is strictly specific to substrates with 5'- phosphates and shows no activity against nucleoside 2'- or 3'- monophosphates. Might be involved in the pyrimidine nucleotide substrate cycles
- Gene Name:
- yjjG
- Uniprot ID:
- P0A8Y1
- Molecular weight:
- 25300
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
- General function:
- Involved in hypoxanthine phosphoribosyltransferase activity
- Specific function:
- This enzyme acts exclusively on hypoxanthine; it does not act on guanine
- Gene Name:
- hpt
- Uniprot ID:
- P0A9M2
- Molecular weight:
- 20115
Reactions
IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in nucleoside metabolic process
- Specific function:
- Acts on guanine, xanthine and to a lesser extent hypoxanthine
- Gene Name:
- gpt
- Uniprot ID:
- P0A9M5
- Molecular weight:
- 16971
Reactions
XMP + diphosphate = 5-phospho-alpha-D-ribose 1-diphosphate + xanthine. |
- 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
- Uniprot ID:
- P0AE22
- Molecular weight:
- 26103
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Catalyzes the hydrolysis of 4-amino-2-methyl-5- hydroxymethylpyrimidine pyrophosphate (HMP-PP) to 4-amino-2- methyl-5-hydroxymethylpyrimidine phosphate (HMP-P), and hydrolysis of thiamine pyrophosphate (TPP) to thiamine monophosphate (TMP). Can hydrolyze other substrates such as MeO-HMP-PP, CF(3)-HMP-PP and MeO-TPP. Is also a non-specific nucleoside tri- and diphosphatase that releases inorganic orthophosphate
- Gene Name:
- nudJ
- Uniprot ID:
- P0AEI6
- Molecular weight:
- 17433
- General function:
- Involved in phosphotransferase activity, alcohol group as acceptor
- Specific function:
- ATP + inosine = ADP + IMP
- Gene Name:
- gsk
- Uniprot ID:
- P0AEW6
- Molecular weight:
- 48448
Reactions
ATP + inosine = ADP + IMP. |
- General function:
- Involved in nucleoside-triphosphate diphosphatase activity
- Specific function:
- Specific function unknown
- Gene Name:
- mazG
- Uniprot ID:
- P0AEY3
- Molecular weight:
- 30412
Reactions
ATP + H(2)O = AMP + diphosphate. |
- General function:
- Involved in cobalamin 5'-phosphate synthase activity
- Specific function:
- Joins Ado-cobinamide-GDP and alpha-ribazole to generate adenosylcobalamin (Ado-cobalamin)
- Gene Name:
- cobS
- Uniprot ID:
- P36561
- Molecular weight:
- 26385
Reactions
GDP-cobinamide + alpha-ribazole = cobalamin + GMP. |
- 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
- Uniprot ID:
- P52061
- Molecular weight:
- 21039
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
- Uniprot ID:
- P60546
- Molecular weight:
- 23593
Reactions
ATP + GMP = ADP + GDP. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the irreversible NADPH-dependent deamination of GMP to IMP. It functions in the conversion of nucleobase, nucleoside and nucleotide derivatives of G to A nucleotides, and in maintaining the intracellular balance of A and G nucleotides
- Gene Name:
- guaC
- Uniprot ID:
- P60560
- Molecular weight:
- 37383
Reactions
Inosine 5'-phosphate + NH(3) + NADP(+) = guanosine 5'-phosphate + NADPH. |
- 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
- Uniprot ID:
- P69503
- Molecular weight:
- 19859
Reactions
AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in phosphorus-oxygen lyase activity
- Specific function:
- In association with DosC is involved in the production and removal of the second messenger c-di-GMP in response to changing O(2) levels. Has phosphodiesterase (PDE) activity with c- di-GMP (PubMed:15995192), very poor activity on cAMP (PubMed:15995192) but not with cGMP, bis(p-nitrophenyl) phosphate or p-nitrophenyl phosphate (PubMed:11970957). Cyclic-di-GMP is a second messenger which controls cell surface-associated traits in bacteria
- Gene Name:
- dosP
- Uniprot ID:
- P76129
- Molecular weight:
- 90260
Reactions
Cyclic di-3',5'-guanylate + H(2)O = 5'-phosphoguanylyl(3'->5')guanosine. |
- General function:
- Involved in catalytic activity
- Specific function:
- Nucleotidase that shows strict specificity toward deoxyribonucleoside 5'-monophosphates and does not dephosphorylate 5'-ribonucleotides or ribonucleoside 3'-monophosphates. Might be involved in the regulation of all dNTP pools in E.coli
- Gene Name:
- yfbR
- Uniprot ID:
- P76491
- Molecular weight:
- 22708
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
- General function:
- Involved in hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
- Specific function:
- Catalyzes the hydrolysis of GDP-mannose. Can also use other substrates, catalyzing the hydrolysis of the pyrophosphate bond, releasing a nucleoside monophosphate and a phosphorylated moiety, depending on the substrate
- Gene Name:
- nudK
- Uniprot ID:
- P37128
- Molecular weight:
- 21749
Reactions
GDP-mannose + H(2)O = GMP + mannose-1-phosphate. |
- 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
- Uniprot ID:
- P08337
- Molecular weight:
- 14927
Reactions
8-oxo-dGTP + H(2)O = 8-oxo-dGMP + diphosphate. |
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368