Guanosine

Identification

Name
Guanosine
Accession Number
DB02857  (EXPT01622)
Type
Small Molecule
Groups
Experimental, Investigational
Description

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).

Structure
Thumb
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
  • Guo
Categories
UNII
12133JR80S
CAS number
118-00-3
Weight
Average: 283.2407
Monoisotopic: 283.091668551
Chemical Formula
C10H13N5O5
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDNA polymeraseNot AvailableEnterobacteria phage RB69
UPurine nucleoside phosphorylaseNot AvailableHuman
UPurine nucleoside phosphorylaseNot AvailableThermus 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Thioguanine Action PathwayDrug action
Guanine and Guanosine SalvageMetabolic
Purine MetabolismMetabolic
AICA-RibosiduriaDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
Azathioprine Action PathwayDrug action
Adenosine Deaminase DeficiencyDisease
Molybdenum Cofactor DeficiencyDisease
Xanthinuria Type IDisease
Xanthinuria Type IIDisease
Purine MetabolismMetabolic
Purine Nucleoside Phosphorylase DeficiencyDisease
Mercaptopurine Action PathwayDrug action
Adenine Phosphoribosyltransferase Deficiency (APRT)Disease
Adenylosuccinate Lyase DeficiencyDisease
Lesch-Nyhan Syndrome (LNS)Disease
Gout or Kelley-Seegmiller SyndromeDisease
Mitochondrial DNA Depletion SyndromeDisease
Myoadenylate Deaminase DeficiencyDisease
Purine Ribonucleosides DegradationMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
ChEBI
16750
ChEMBL
CHEMBL375655
HET
GMP
Wikipedia
Guanosine
PDB Entries
1ih7 / 1je1 / 1odj / 1rfg / 1waf / 2an9 / 2fqx / 2gbh / 2qvn / 3cfo
show 23 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentCancer, Breast1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)239 dec °CPhysProp
water solubility700 mg/L (at 18 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.90SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility15.3 mg/mLALOGPS
logP-2.1ALOGPS
logP-2.7ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.16ChemAxon
pKa (Strongest Basic)1.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.22 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.62 m3·mol-1ChemAxon
Polarizability26.02 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9831
Blood Brain Barrier+0.943
Caco-2 permeable-0.8893
P-glycoprotein substrateNon-substrate0.6302
P-glycoprotein inhibitor INon-inhibitor0.9723
P-glycoprotein inhibitor IINon-inhibitor0.9771
Renal organic cation transporterNon-inhibitor0.94
CYP450 2C9 substrateNon-substrate0.8524
CYP450 2D6 substrateNon-substrate0.8333
CYP450 3A4 substrateNon-substrate0.5838
CYP450 1A2 substrateNon-inhibitor0.8071
CYP450 2C9 inhibitorNon-inhibitor0.9565
CYP450 2D6 inhibitorNon-inhibitor0.9636
CYP450 2C19 inhibitorNon-inhibitor0.9524
CYP450 3A4 inhibitorNon-inhibitor0.9767
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9927
Ames testNon AMES toxic0.8277
CarcinogenicityNon-carcinogens0.9015
BiodegradationNot ready biodegradable0.9454
Rat acute toxicity1.9927 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9816
hERG inhibition (predictor II)Non-inhibitor0.9322
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)GC-MSsplash10-0f7k-1952000000-c57c052c65f3fa9504af
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0feb-0963000000-c91b93f300b50fbc99c1
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-00di-9440000000-361092fc2dc5206fe655
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)GC-MSsplash10-00di-9421000000-b2b15c03b8206196f59f
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f7k-1952000000-c57c052c65f3fa9504af
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0feb-0963000000-c91b93f300b50fbc99c1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9440000000-361092fc2dc5206fe655
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9421000000-b2b15c03b8206196f59f
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0udi-0900000000-ef0cae7d67f9e803f2b2
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0udi-0900000000-68fb606342b8bb123bb7
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0f89-0900000000-48d32b9d62eda760619e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0f7k-0920000000-f3db23cc762b5fb860e4
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-5da62630f03e15d8707c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-1fa2eb473b57a37ecd45
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0900000000-d71a3d2995d32c692eb7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0390000000-ff54fe98a9c0e1bc104c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-c023445b0f47e6e7267b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0900000000-a094aa75c261cdce24de
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0900000000-e114cc69f7ab438abb39
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001j-0795222100-55ad26c7c4d9f64dd759
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-0900000000-9450dc04b32ca468e146
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0900000000-0147dd895ffbecfa9668
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03di-0190000000-5d00bb466dd23f062b86
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0f89-0690030010-86fae3a6cae3e2b3de2c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001i-0900000000-97217b0084eeac14e7e1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0900000000-d0c65e36192b7ebdaae8
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001i-0090000000-bb8ef433eba795395fe3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-001i-0090000000-4ceff605ca97b7c0774a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0ue9-0960000000-1c286e55d437f33a29b3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0udi-0900000000-7149427a8c09f429fdbe
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0zgi-0900000000-5de849ca7144ca8afe05
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-053r-0900000000-f97dbc10f152af4df778
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0ue9-0970000000-045435f1be487a94195c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0udi-0900000000-d86f84e430691047e637
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0udi-0900000000-7ab32f15c115e84b6a1a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0udi-0900000000-2ba7a06f48061d0fe9db
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0f79-0900000000-4ed5ef88e022858add62
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0udi-0900000000-dd426e6b477a5f3f08d6
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0udi-0900000000-3a8b3c6f078ce1f79701
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0f89-0590000000-12615cea517dfdcb46c9
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-0udi-0930000000-7da21523b033716a30ee
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0ue9-0910000000-bd6d397c6e5507b168b0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0090000000-4ceff605ca97b7c0774a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0ue9-0960000000-1c286e55d437f33a29b3
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0900000000-7149427a8c09f429fdbe
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0zgi-0900000000-5de849ca7144ca8afe05
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-053r-0900000000-683b3e71755dc9d017bb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-0147dd895ffbecfa9668
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-001i-0900000000-97217b0084eeac14e7e1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-d0c65e36192b7ebdaae8
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-001i-0090000000-bb8ef433eba795395fe3
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0ue9-0910000000-bd6d397c6e5507b168b0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ue9-0970000000-045435f1be487a94195c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-d86f84e430691047e637
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-7ab32f15c115e84b6a1a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-2ba7a06f48061d0fe9db
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0f79-0900000000-4ed5ef88e022858add62
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0udi-0900000000-69de32f0be4f1ea16391
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-d71a3d2995d32c692eb7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-c023445b0f47e6e7267b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-a094aa75c261cdce24de
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-e114cc69f7ab438abb39
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0f89-0590000000-12615cea517dfdcb46c9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0930000000-7da21523b033716a30ee
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Purine nucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Imidazopyrimidine / Purine / Hydroxypyrimidine / Monosaccharide / N-substituted imidazole / Pyrimidine
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
guanosines (CHEBI:16750) / Ribonucleosides (C00387)

Targets

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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
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 on June 13, 2005 07:24 / Updated on October 01, 2018 13:26