Guanosine (CHEM003409)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:22 UTC
Update Date2026-04-13 21:59:51 UTC
Accession NumberCHEM003409
Identification
Common NameGuanosine
ClassSmall Molecule
DescriptionGuanosine 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
Thumb
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0f7k-1952000000-c57c052c65f3fa9504afSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0feb-0963000000-c91b93f300b50fbc99c1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9440000000-361092fc2dc5206fe655Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-9421000000-b2b15c03b8206196f59fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7k-1952000000-c57c052c65f3fa9504afSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0feb-0963000000-c91b93f300b50fbc99c1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9440000000-361092fc2dc5206fe655Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9421000000-b2b15c03b8206196f59fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zml-9670000000-793c36e66ed6430b932bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0159-4945800000-86e8114119c47d85cc53Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-ef0cae7d67f9e803f2b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-68fb606342b8bb123bb7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f89-0900000000-48d32b9d62eda760619eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f7k-0920000000-f3db23cc762b5fb860e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-5da62630f03e15d8707cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-1fa2eb473b57a37ecd45Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-d71a3d2995d32c692eb7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0390000000-ff54fe98a9c0e1bc104cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-c023445b0f47e6e7267bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-a094aa75c261cdce24deSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-e114cc69f7ab438abb39Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001j-0795222100-55ad26c7c4d9f64dd759Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-9450dc04b32ca468e146Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-0147dd895ffbecfa9668Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-5d00bb466dd23f062b86Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0f89-0690030010-86fae3a6cae3e2b3de2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-97217b0084eeac14e7e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-d0c65e36192b7ebdaae8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0090000000-bb8ef433eba795395fe3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0090000000-4ceff605ca97b7c0774aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0ue9-0960000000-1c286e55d437f33a29b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-0900000000-7149427a8c09f429fdbeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0zgi-0900000000-5de849ca7144ca8afe05Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-053r-0900000000-f97dbc10f152af4df778Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0ue9-0970000000-045435f1be487a94195cSpectrum
MSMass Spectrum (Electron Ionization)splash10-0udl-9400000000-5a915ef7129c50e638a7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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
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.