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Identification
NameGuanosine
Accession NumberDB02857  (EXPT01622)
TypeSmall Molecule
GroupsExperimental
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). [Wikipedia]

Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number118-00-3
WeightAverage: 283.2407
Monoisotopic: 283.091668551
Chemical FormulaC10H13N5O5
InChI KeyNYHBQMYGNKIUIF-BZKDHIKHSA-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+/m0/s1
IUPAC Name
2-amino-9-[(2R,3R,4R,5S)-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine ribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Purinone
  • Hypoxanthine
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Lactam
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Molybdenum Cofactor DeficiencyDiseaseSMP00203
Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
Mitochondrial DNA depletion syndromeDiseaseSMP00536
Purine MetabolismMetabolicSMP00050
Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
Azathioprine Action PathwayDrug actionSMP00427
Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
Mercaptopurine Action PathwayDrug actionSMP00428
Xanthinuria type IDiseaseSMP00512
Adenosine Deaminase DeficiencyDiseaseSMP00144
AICA-RibosiduriaDiseaseSMP00168
Thioguanine Action PathwayDrug actionSMP00430
Myoadenylate deaminase deficiencyDiseaseSMP00537
Lesch-Nyhan Syndrome (LNS)DiseaseSMP00364
Xanthine Dehydrogenase Deficiency (Xanthinuria)DiseaseSMP00220
Xanthinuria type IIDiseaseSMP00513
Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9565
CYP450 2D6 substrateNon-inhibitor0.9636
CYP450 2C19 substrateNon-inhibitor0.9524
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point239 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
Polarizability25.99 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. DNA polymerase

Kind: protein

Organism: Enterobacteria phage RB69

Pharmacological action: unknown

Components

Name UniProt ID Details
DNA polymerase Q38087 Details

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
  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

2. Purine nucleoside phosphorylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Purine nucleoside phosphorylase P00491 Details

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
  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

3. Purine nucleoside phosphorylase

Kind: protein

Organism: Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)

Pharmacological action: unknown

Components

Name UniProt ID Details
Purine nucleoside phosphorylase Q5SID9 Details
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:19