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Guanosine (M2MDB000052)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:21:42 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers | 
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Guanosine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate). (Wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: | 
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| Chemical Formula: | C10H13N5O5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 283.2407 Monoisotopic: 283.091668551  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | NYHBQMYGNKIUIF-UUOKFMHZSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 118-00-3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | guanosine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Purine nucleosides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Purine nucleosides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents | 
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| Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors | 
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 239 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: | 
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| Predicted Properties | 
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: |  Guanosine monophosphate + Water > Guanosine + Phosphate Guanosine + Phosphate <> Guanine + Ribose-1-phosphate Guanosine triphosphate + Water > Guanosine + Triphosphate Adenosine triphosphate + Guanosine > ADP + Guanosine monophosphate + Hydrogen ion Guanosine 3'-phosphate + Water > Guanosine + Phosphate Guanosine monophosphate + Water <> Guanosine + Phosphate Adenosine triphosphate + Guanosine <> ADP + Guanosine monophosphate Guanosine + Water <> Guanine + Ribose Guanosine + Phosphate <> Guanine + alpha-D-Ribose 1-phosphate Guanosine + Phosphate > Ribose-1-phosphate + Guanine  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: | 
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| KEGG Pathways: | 
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| EcoCyc Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
   Find out more about how we convert literature concentrations.   | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: | 
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| Synthesis Reference: | Tang, Shengrong; Huang, Weihong; Hou, Zuorong. Process of guanosine production by fermentation. Gongye Weishengwu (1998), 28(4), 11-16. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: | 
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Enzymes
- 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:
 - This bifunctional enzyme catalyzes two consecutive reactions during ribonucleic acid degradation. Converts a 2',3'- cyclic nucleotide to a 3'-nucleotide and then the 3'-nucleotide to the corresponding nucleoside and phosphate
 - Gene Name:
 - cpdB
 - Uniprot ID:
 - P08331
 - Molecular weight:
 - 70832
 
Reactions
| Nucleoside 2',3'-cyclic phosphate + H(2)O = nucleoside 3'-phosphate. | 
| A 3'-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 purine-nucleoside phosphorylase activity
 - Specific function:
 - Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
 - Gene Name:
 - deoD
 - Uniprot ID:
 - P0ABP8
 - Molecular weight:
 - 25950
 
Reactions
| Purine nucleoside + phosphate = purine + alpha-D-ribose 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
 - Uniprot ID:
 - P0AE22
 - Molecular weight:
 - 26103
 
Reactions
| A phosphate monoester + H(2)O = an alcohol + phosphate. | 
- 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 magnesium ion binding
 - Specific function:
 - dGTPase preferentially hydrolyzes dGTP over the other canonical NTPs
 - Gene Name:
 - dgt
 - Uniprot ID:
 - P15723
 - Molecular weight:
 - 59382
 
Reactions
| dGTP + H(2)O = deoxyguanosine + triphosphate. | 
- General function:
 - Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
 - Specific function:
 - Hydrolyzes cytidine or uridine to ribose and cytosine or uracil, respectively. Has a clear preference for cytidine over uridine. Strictly specific for ribonucleosides. Has a low but significant activity for the purine nucleoside xanthosine
 - Gene Name:
 - rihB
 - Uniprot ID:
 - P33022
 - Molecular weight:
 - 33748
 
Reactions
| A pyrimidine nucleoside + H(2)O = D-ribose + a pyrimidine base. | 
- 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 purine-nucleoside phosphorylase activity
 - Specific function:
 - The nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the nucleoside molecule, with the formation of the corresponding free bases and pentose-1-phosphate. This protein can degrade all purine nucleosides except adenosine and deoxyadenosine
 - Gene Name:
 - xapA
 - Uniprot ID:
 - P45563
 - Molecular weight:
 - 29834
 
Transporters
- General function:
 - Involved in nucleoside transmembrane transporter activity
 - Specific function:
 - Transports nucleosides with a high affinity. Driven by a proton motive force
 - Gene Name:
 - nupG
 - Uniprot ID:
 - P0AFF4
 - Molecular weight:
 - 46389
 
- General function:
 - Involved in nucleoside:sodium symporter activity
 - Specific function:
 - Nucleoside transporter
 - Gene Name:
 - nupX
 - Uniprot ID:
 - P33021
 - Molecular weight:
 - 43409
 
- 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