General Information of MET (ID: META00173)
Name Guanosine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
2(3H)-Imino-9-beta-D-ribofuranosyl-9H-purin-6(1H)-one; 2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one; 2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one; 2-Amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one; 2-Amino-inosine; 9-beta-D-Ribofuranosyl-guanine; 9-beta-delta-Ribofuranosyl-guanine; G; Guanine riboside; Guanine-9-beta-D-ribofuranoside; Guanosin; Guo; Ribonucleoside; Vernine; b-D-Ribofuranoside guanine-9; beta-delta-Ribofuranoside guanine-9
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Drug;Cosmetic;TCM Ingredients;Microbial
Structure Type   Purine nucleosides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Purine nucleosides
PubChem CID
6802
HMDB ID
HMDB0000133
Formula
C10H13N5O5
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00387
DrugBank ID
DB02857
ChEBI ID
16750
FooDB ID
FDB003632
ChemSpider ID
6544
METLIN ID
87
Physicochemical Properties Molecular Weight 283.2407 Topological Polar Surface Area N.A.
XlogP N.A. Complexity N.A.
Heavy Atom Count N.A. Rotatable Bond Count N.A.
Hydrogen Bond Donor Count N.A. Hydrogen Bond Acceptor Count N.A.
Function
Guanosine (G), also known as 2-amino-inosine, 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. Guanosine consists of a guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine is a moderately basic compound (based on its pKa). Guanosine exists in all living species, ranging from bacteria to humans. In humans, guanosine is involved in intracellular signalling through adenosine receptor A2B and adenosine. Outside of the human body, guanosine has been detected, but not quantified in, several different foods, such as leeks, garlic, chicory roots, green bell peppers, and black-eyed peas. This could make guanosine a potential biomarker for the consumption of these foods. Guanosine plays an important role in various biochemical processes such as the synthesis of nucleic acids and proteins, photosynthesis, muscle contraction, and intracellular signal transduction (cGMP). Guanosine is a potentially toxic compound. It is very soluble in acetic acid, slightly soluble in water, and insoluble in ethanol, diethyl ether, benzene, and chloroform. The antiviral drug acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are both structurally similar to guanosine. Guanosine was also used to make regadenoson. Guanosine is a white, crystalline powder with no odour and a mild saline taste. Guanosine is required for an RNA splicing reaction in mRNA when a "self-splicing" intron removes itself from the mRNA by cutting at both ends, re-ligating, and leaving just the exons on either side to be translated into protein. When guanine is attached by its N9 nitrogen to the C1 carbon of a deoxyribose ring it is known as deoxyguanosine. Guanosine can be found in clovers, coffee plants, and the pollen of pines. Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP).
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Guanosine concentration: increase (FC = 2.75 - 4.35)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of guanosine levels compared with control group.
      Nitrogen permease regulator (NPR)
            Natriuretic peptide receptor B (NPR2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Deletion of NPR2
                      Induced Change Guanosine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that deletion of NPR2 leads to the increase of guanosine levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockout of TP53
                      Induced Change Guanosine concentration: increase (Log2 FC=10.49)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of guanosine levels compared with control group.
      Sugar transporter (ST)
            Facilitated glucose transporter 1 (SLC2A1A) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Downregulation of slc2a1a caused by Yap loss-of-function mutation
                      Induced Change Guanosine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that downregulation of slc2a1a caused by Yap loss-of-function mutation leads to the decrease of guanosine levels compared with control group.
      Transcriptional coactivator (TC)
            Transcriptional coactivator YAP1 (yap1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Decrease of Yap mRNA caused by Yap loss-of-function mutation
                      Induced Change Guanosine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that decrease of Yap mRNA caused by Yap loss-of-function mutation leads to the decrease of guanosine levels compared with control group.
      Transferases (EC 2)
            Transaldolase (TALDO1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [5]
                      Introduced Variation Knockout of Taldo1
                      Induced Change Guanosine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Taldo1 leads to the increase of guanosine levels compared with control group.
References
1 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
2 Npr2 inhibits TORC1 to prevent inappropriate utilization of glutamine for biosynthesis of nitrogen-containing metabolites. Sci Signal. 2014 Dec 16;7(356):ra120.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.
4 Yap regulates glucose utilization and sustains nucleotide synthesis to enable organ growth. EMBO J. 2018 Nov 15;37(22):e100294.
5 Two isoforms of TALDO1 generated by alternative translational initiation show differential nucleocytoplasmic distribution to regulate the global metabolic network. Sci Rep. 2016 Oct 5;6:34648.

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