You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Record Information
Version1.0
Creation Date2016-09-30 22:20:00 UTC
Update Date2020-06-04 20:45:00 UTC
MCDB ID BMDB0000133
Secondary Accession Numbers
  • BMDB00133
Metabolite Identification
Common NameGuanosine
DescriptionGuanosine, also known as G or 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 exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Guanosine exists in all living species, ranging from bacteria to humans. In cattle, guanosine is involved in a couple of metabolic pathways, which include the intracellular signalling through adenosine receptor A2A and adenosine pathway and the intracellular signalling through adenosine receptor A2B and adenosine pathway. Guanosine is a potentially toxic compound.
Structure
Thumb
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 Weight283.2407
Monoisotopic Molecular Weight283.091668551
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
CAS Registry Number118-00-3
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1
InChI Identifier
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
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point239 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.7 mg/mL at 18 °CNot Available
LogP-1.9SANGSTER (1993)
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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-c57c052c65f3fa9504afJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0feb-0963000000-c91b93f300b50fbc99c1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9440000000-361092fc2dc5206fe655JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-9421000000-b2b15c03b8206196f59fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7k-1952000000-c57c052c65f3fa9504afJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0feb-0963000000-c91b93f300b50fbc99c1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9440000000-361092fc2dc5206fe655JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9421000000-b2b15c03b8206196f59fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zml-9670000000-793c36e66ed6430b932bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0159-4945800000-86e8114119c47d85cc53JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-ef0cae7d67f9e803f2b2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-68fb606342b8bb123bb7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f89-0900000000-48d32b9d62eda760619eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f7k-0920000000-f3db23cc762b5fb860e4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-5da62630f03e15d8707cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-1fa2eb473b57a37ecd45JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-d71a3d2995d32c692eb7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0390000000-ff54fe98a9c0e1bc104cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-c023445b0f47e6e7267bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-a094aa75c261cdce24deJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-e114cc69f7ab438abb39JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001j-0795222100-55ad26c7c4d9f64dd759JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-9450dc04b32ca468e146JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-0147dd895ffbecfa9668JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-5d00bb466dd23f062b86JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0f89-0690030010-86fae3a6cae3e2b3de2cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-97217b0084eeac14e7e1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-d0c65e36192b7ebdaae8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0090000000-bb8ef433eba795395fe3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0090000000-4ceff605ca97b7c0774aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0ue9-0960000000-1c286e55d437f33a29b3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-0900000000-7149427a8c09f429fdbeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0zgi-0900000000-5de849ca7144ca8afe05JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-053r-0900000000-f97dbc10f152af4df778JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0ue9-0970000000-045435f1be487a94195cJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0udl-9400000000-5a915ef7129c50e638a7JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.83 +/- 0.32 uM details
Detected and Quantified0.8 uM details
HMDB IDHMDB0000133
DrugBank IDDB02857
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003632
KNApSAcK IDC00019679
Chemspider ID6544
KEGG Compound IDC00387
BioCyc IDGUANOSINE
BiGG ID51567
Wikipedia LinkGuanosine
METLIN ID87
PubChem Compound6802
PDB IDNot Available
ChEBI ID16750
References
Synthesis ReferenceTang, Shengrong; Huang, Weihong; Hou, Zuorong. Process of guanosine production by fermentation. Gongye Weishengwu (1998), 28(4), 11-16.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. [PubMed:1897275 ]
  2. 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. [PubMed:11242448 ]
  3. 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. [PubMed:28306241 ]