Identification
- Generic Name
- Guanosine
- DrugBank Accession Number
- DB02857
- Background
Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate) which are factors in signal transduction pathways.
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for Guanosine (DB02857)
- Weight
- Average: 283.2407
Monoisotopic: 283.091668551 - Chemical Formula
- C10H13N5O5
- Synonyms
- 2-amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-one
- 2(3H)-imino-9-β-D-ribofuranosyl-9H-purin-6(1H)-one
- 9-β-D-ribofuranosyl-guanine
- Guanine riboside
- Guanine-9-β-D-ribofuranoside
- Guanosin
- Guanosina
- Guo
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDNA polymerase Not Available Enterobacteria phage RB69 UPurine nucleoside phosphorylase Not Available Humans UPurine nucleoside phosphorylase Not Available Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Adenylosuccinate Lyase Deficiency Disease Xanthine Dehydrogenase Deficiency (Xanthinuria) Disease Xanthinuria Type I Disease Mitochondrial DNA Depletion Syndrome Disease Myoadenylate Deaminase Deficiency Disease Purine Metabolism Metabolic Purine Nucleoside Phosphorylase Deficiency Disease Lesch-Nyhan Syndrome (LNS) Disease Gout or Kelley-Seegmiller Syndrome Disease Mercaptopurine Action Pathway Drug action Adenine Phosphoribosyltransferase Deficiency (APRT) Disease Adenosine Deaminase Deficiency Disease AICA-Ribosiduria Disease Molybdenum Cofactor Deficiency Disease Azathioprine Action Pathway Drug action Thioguanine Action Pathway Drug action Xanthinuria Type II Disease - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as purine nucleosides. These 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
- Glycosylamines / Pentoses / Purines and purine derivatives / Hydroxypyrimidines / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds show 4 more
- Substituents
- Alcohol / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyrimidine / Imidazole / Imidazopyrimidine show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- guanosines (CHEBI:16750) / Ribonucleosides (C00387)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 12133JR80S
- CAS number
- 118-00-3
- 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
- IUPAC Name
- 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
- SMILES
- NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1
References
- Synthesis Reference
Hitoshi Enei, Katsuaki Sato, Yoshio Hirose, "Method of producing guanosine by fermentation." U.S. Patent US3960660, issued April, 1971.
US3960660- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000133
- KEGG Compound
- C00387
- PubChem Compound
- 6802
- PubChem Substance
- 46505099
- ChemSpider
- 6544
- BindingDB
- 50366814
- 1591890
- ChEBI
- 16750
- ChEMBL
- CHEMBL375655
- ZINC
- ZINC000001550030
- PDBe Ligand
- GMP
- Wikipedia
- Guanosine
- PDB Entries
- 1ih7 / 1je1 / 1odj / 1rfg / 1waf / 2an9 / 2fqx / 2gbh / 2qvn / 3cfo … show 39 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 239 dec °C PhysProp water solubility 700 mg/L (at 18 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -1.90 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 15.3 mg/mL ALOGPS logP -2.1 ALOGPS logP -2.7 Chemaxon logS -1.3 ALOGPS pKa (Strongest Acidic) 10.16 Chemaxon pKa (Strongest Basic) 0.45 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 155.22 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 64.62 m3·mol-1 Chemaxon Polarizability 26.03 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9831 Blood Brain Barrier + 0.943 Caco-2 permeable - 0.8893 P-glycoprotein substrate Non-substrate 0.6302 P-glycoprotein inhibitor I Non-inhibitor 0.9723 P-glycoprotein inhibitor II Non-inhibitor 0.9771 Renal organic cation transporter Non-inhibitor 0.94 CYP450 2C9 substrate Non-substrate 0.8524 CYP450 2D6 substrate Non-substrate 0.8333 CYP450 3A4 substrate Non-substrate 0.5838 CYP450 1A2 substrate Non-inhibitor 0.8071 CYP450 2C9 inhibitor Non-inhibitor 0.9565 CYP450 2D6 inhibitor Non-inhibitor 0.9636 CYP450 2C19 inhibitor Non-inhibitor 0.9524 CYP450 3A4 inhibitor Non-inhibitor 0.9767 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9927 Ames test Non AMES toxic 0.8277 Carcinogenicity Non-carcinogens 0.9015 Biodegradation Not ready biodegradable 0.9454 Rat acute toxicity 1.9927 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9816 hERG inhibition (predictor II) Non-inhibitor 0.9322
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 173.6019414 predictedDarkChem Lite v0.1.0 [M-H]- 174.7928414 predictedDarkChem Lite v0.1.0 [M-H]- 160.48112 predictedDeepCCS 1.0 (2019) [M+H]+ 173.9345414 predictedDarkChem Lite v0.1.0 [M+H]+ 174.6538414 predictedDarkChem Lite v0.1.0 [M+H]+ 162.83914 predictedDeepCCS 1.0 (2019) [M+Na]+ 174.2573414 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.0838414 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.06738 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Enterobacteria phage RB69
- Pharmacological action
- Unknown
- General Function
- Nucleotide binding
- Specific Function
- Replicates the viral genomic DNA. This polymerase possesses two enzymatic activities: DNA synthesis (polymerase) and an exonucleolytic activity that degrades single-stranded DNA in the 3'- to 5'-di...
- Gene Name
- 43
- Uniprot ID
- Q38087
- Uniprot Name
- DNA polymerase
- Molecular Weight
- 104612.37 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Purine-nucleoside phosphorylase activity
- Specific Function
- The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine ...
- Gene Name
- PNP
- Uniprot ID
- P00491
- Uniprot Name
- Purine nucleoside phosphorylase
- Molecular Weight
- 32117.69 Da
References
- Kind
- Protein
- Organism
- Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
- Pharmacological action
- Unknown
- General Function
- Transferase activity, transferring pentosyl groups
- Specific Function
- Not Available
- Gene Name
- Not Available
- Uniprot ID
- Q5SID9
- Uniprot Name
- Purine nucleoside phosphorylase
- Molecular Weight
- 25414.93 Da
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52