Record Information
Version1.0
Creation date2010-04-08 22:05:53 UTC
Update date2019-11-26 02:59:26 UTC
Primary IDFDB003632
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGuanosine
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. (PMID: 16325434); Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a ?-N9-glycosidic bond. Guanosine is found in many foods, some of which are elderberry, malus (crab apple), acerola, and arrowhead.
CAS Number118-00-3
Structure
Thumb
Synonyms
SynonymSource
2-amino-1,9-dihydro-9-b-D-Ribofuranosyl-6H-purin-6-oneGenerator
2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-onebiospider
2-amino-1,9-dihydro-9-beta-delta-Ribofuranosyl-6H-purin-6-oneHMDB
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-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-onebiospider
2-amino-9-β-D-ribofuranosyl-1,9-dihydro-6H-purin-6-oneGenerator
2-amino-Inosinebiospider
2(3H)-Imino-9-b-D-ribofuranosyl-9H-purin-6(1H)-oneGenerator
2(3H)-Imino-9-beta-D-ribofuranosyl-9H-purin-6(1H)-onebiospider
2(3H)-Imino-9-β-D-ribofuranosyl-9H-purin-6(1H)-oneGenerator
9-(beta-D-Ribofuranosyl)guaninebiospider
9-β-d-Arabinofuranosylguaninebiospider
9-b-D-ribofuranosyl-Guaninebiospider
9-beta-D-Ribofuranosyl-guanineChEBI
9-beta-D-Ribofuranosylguaninebiospider
9-beta-delta-ribofuranosyl-Guaninebiospider
9-β-D-ribofuranosyl-guanineGenerator
Arabinosylguaninebiospider
b-D-Ribofuranoside guanine-9biospider
beta-delta-Ribofuranoside guanine-9biospider
Guanine ribosidebiospider
Guanine-9-b-D-ribofuranosideGenerator
Guanine-9-beta-D-ribofuranosidebiospider
Guanine-9-β-D-ribofuranosideGenerator
Guanosinbiospider
GuoChEBI
Nucleoside qbiospider
RibonucleosideHMDB
Verninebiospider
Predicted Properties
PropertyValueSource
Water Solubility8.98 g/LALOGPS
logP-1.8ALOGPS
logP-2ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)5.98ChemAxon
pKa (Strongest Basic)2.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.21 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.2 m³·mol⁻¹ChemAxon
Polarizability25.97 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H13N5O5
IUPAC name2-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
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)
InChI KeyNYHBQMYGNKIUIF-UHFFFAOYSA-N
Isomeric SMILESNC1=NC(=O)C2=C(N1)N(C=N2)C1OC(CO)C(O)C1O
Average Molecular Weight283.2407
Monoisotopic Molecular Weight283.091668551
Classification
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
  • 6-oxopurine
  • Hypoxanthine
  • Pentose monosaccharide
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Primary amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point239 oC
Boiling PointNot Available
Experimental Water Solubility0.7 mg/mL at 18 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.90SANGSTER (1993)
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0940000000-014154bc8610aff473dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-b6426336b06d5dbb1c36JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1900000000-b114a756c5bf0507d0fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0690000000-0f44b23ec32853a8e29fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-63680361521d2fdefd66JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbc-4900000000-1e17d384c6f46110a087JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0udl-9400000000-5a915ef7129c50e638a7JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID6544
ChEMBL IDCHEMBL375655
KEGG Compound IDC00387
Pubchem Compound ID6802
Pubchem Substance IDNot Available
ChEBI ID16750
Phenol-Explorer IDNot Available
DrugBank IDDB02857
HMDB IDHMDB00133
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGUANOSINE
BIGG ID51567
KNApSAcK IDNot Available
HET IDGMP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGuanosine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Purine nucleoside phosphorylasePNPP00491
Cytosolic 5'-nucleotidase 3NT5C3Q9H0P0
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).