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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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassGlycosyl Compounds
Direct parentPurine Nucleosides and Analogues
Alternative parentsHypoxanthines; Pentoses; Pyrimidones; N-substituted Imidazoles; Primary Aromatic Amines; Tetrahydrofurans; Oxolanes; Secondary Alcohols; 1,2-Diols; Primary Alcohols; Ethers; Polyamines
Substituentspentose monosaccharide; purinone; hypoxanthine; purine; imidazopyrimidine; pyrimidone; primary aromatic amine; pyrimidine; n-substituted imidazole; monosaccharide; tetrahydrofuran; oxolane; azole; imidazole; 1,2-diol; secondary alcohol; polyamine; ether; primary alcohol; primary amine; amine; organonitrogen compound; alcohol
Classification descriptionThis compound belongs to the purine nucleosides and analogues. These are compounds comprising a purine base attached to a sugar.
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
Molybdenium Cofactor DeficiencyDiseaseSMP00203
Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
Mitochondrial DNA depletion syndromeDiseaseSMP00536
Purine MetabolismMetabolicSMP00050
Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
Xanthinuria type IDiseaseSMP00512
Lesch-Nyhan Syndrome (LNS)DiseaseSMP00364
Xanthine Dehydrogenase Deficiency (Xanthinuria)DiseaseSMP00220
Xanthinuria type IIDiseaseSMP00513
Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
Adenosine Deaminase DeficiencyDiseaseSMP00144
AICA-RibosiduriaDiseaseSMP00168
Myoadenylate deaminase deficiencyDiseaseSMP00537
Azathioprine Action PathwayDrug actionSMP00427
Mercaptopurine Action PathwayDrug actionSMP00428
Thioguanine Action PathwayDrug actionSMP00430
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9831
Blood Brain Barrier + 0.943
Caco-2 permeable - 0.8893
P-glycoprotein substrate Non-substrate 0.6302
P-glycoprotein inhibitor I Non-inhibitor 0.9723
P-glycoprotein inhibitor II Non-inhibitor 0.9771
Renal organic cation transporter Non-inhibitor 0.94
CYP450 2C9 substrate Non-substrate 0.8524
CYP450 2D6 substrate Non-substrate 0.8333
CYP450 3A4 substrate Non-substrate 0.5838
CYP450 1A2 substrate Non-inhibitor 0.8071
CYP450 2C9 substrate Non-inhibitor 0.9565
CYP450 2D6 substrate Non-inhibitor 0.9636
CYP450 2C19 substrate Non-inhibitor 0.9524
CYP450 3A4 substrate Non-inhibitor 0.9767
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9927
Ames test Non AMES toxic 0.8277
Carcinogenicity Non-carcinogens 0.9015
Biodegradation Not ready biodegradable 0.9454
Rat acute toxicity 1.9927 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9816
hERG inhibition (predictor II) Non-inhibitor 0.9322
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 Solubility15.3ALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
ResourceLink
KEGG CompoundC00387
PubChem Compound453549
PubChem Substance46505099
ChEBI16750
ChEMBL
HETGMP
WikipediaGuanosine
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