Guanosine (CHEM003409)

Record Information
Version1.0
Creation Date2014-08-29 06:51:22 UTC
Update Date2026-05-14 17:46:48 UTC
Accession NumberCHEM003409
Identification
Common NameGuanosine
ClassSmall Molecule
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). . The nucleoside guanosine exert important neuroprotective and neuromodulator roles in the central nervous system, which may be related to inhibition of the glutamatergic neurotransmission activity. Guanosine is the specific extracellular guanine-based purines effector and indicate that its conversion occurs not only in the central nervous system but also peripherally. (1).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Ether
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2(3H)-Imino-9-beta-D-ribofuranosyl-9H-purin-6(1H)-oneChEBI
2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-oneChEBI
2-Amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-oneChEBI
9-beta-D-Ribofuranosyl-guanineChEBI
GChEBI
Guanine ribosideChEBI
Guanine-9-beta-D-ribofuranosideChEBI
GuanosinChEBI
GuoChEBI
2(3H)-Imino-9-b-D-ribofuranosyl-9H-purin-6(1H)-oneGenerator
2(3H)-Imino-9-β-D-ribofuranosyl-9H-purin-6(1H)-oneGenerator
2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-oneGenerator
2-Amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-oneGenerator
2-Amino-9-b-D-ribofuranosyl-1,9-dihydro-6H-purin-6-oneGenerator
2-Amino-9-β-D-ribofuranosyl-1,9-dihydro-6H-purin-6-oneGenerator
9-b-D-Ribofuranosyl-guanineGenerator
9-Β-D-ribofuranosyl-guanineGenerator
Guanine-9-b-D-ribofuranosideGenerator
Guanine-9-β-D-ribofuranosideGenerator
2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-oneHMDB
2-Amino-inosineHMDB
9-beta-delta-Ribofuranosyl-guanineHMDB
b-D-Ribofuranoside guanine-9HMDB
beta-delta-Ribofuranoside guanine-9HMDB
RibonucleosideHMDB
VernineHMDB
Chemical FormulaC10H13N5O5
Average Molecular Mass283.241 g/mol
Monoisotopic Mass283.092 g/mol
CAS Registry Number118-00-3
IUPAC Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
Traditional Nameguanosine
SMILESNC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1
InChI IdentifierInChI=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
InChI KeyNYHBQMYGNKIUIF-UUOKFMHZSA-N
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Extracellular
  • Lysosome
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
Purine Nucleoside Phosphorylase DeficiencySMP00210 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point239°C
Boiling PointNot Available
Solubility0.7 mg/mL at 18°C
Predicted Properties
PropertyValueSource
Water Solubility15.3 g/LALOGPS
logP-2.1ALOGPS
logP-2.7ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.16ChemAxon
pKa (Strongest Basic)0.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.62 m³·mol⁻¹ChemAxon
Polarizability26.03 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB02857
HMDB IDHMDB0000133
FooDB IDFDB003632
Phenol Explorer IDNot Available
KNApSAcK IDC00019679
BiGG ID51567
BioCyc IDGUANOSINE
METLIN ID87
PDB IDNot Available
Wikipedia LinkGuanosine
Chemspider ID6544
ChEBI ID16750
PubChem Compound ID6802
Kegg Compound IDC00387
YMDB IDYMDB00509
ECMDB IDECMDB00133
References
Synthesis Reference

Hitoshi Enei, Katsuaki Sato, Yoshio Hirose, “Method of producing guanosine by fermentation.” U.S. Patent US3960660, issued April, 1971.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11434576
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15471343
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15920424
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17060520
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17202332
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18191898
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18549801
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21435378
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21500353
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21515778
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21671255
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21774919
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=2559771
14. Tang, Shengrong; Huang, Weihong; Hou, Zuorong. Process of guanosine production by fermentation. Gongye Weishengwu (1998), 28(4), 11-16.
15. Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52.
16. Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68.
17. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.
18. Tang, Shengrong; Huang, Weihong; Hou, Zuorong. Process of guanosine production by fermentation. Gongye Weishengwu (1998), 28(4), 11-16.
19. Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7.
20. Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48.
21. Hartwick RA, Krstulovic AM, Brown PR: Identification and quantitation of nucleosides, bases and other UV-absorbing compounds in serum, using reversed-phase high-performance liquid chromatography. II. Evaluation of human sera. J Chromatogr. 1979 Dec 30;186:659-76.
22. Traut TW: Physiological concentrations of purines and pyrimidines. Mol Cell Biochem. 1994 Nov 9;140(1):1-22.
23. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
24. Saute JA, da Silveira LE, Soares FA, Martini LH, Souza DO, Ganzella M: Amnesic effect of GMP depends on its conversion to guanosine. Neurobiol Learn Mem. 2006 May;85(3):206-12. Epub 2005 Dec 1.