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Identification
NameGuanine
Accession NumberDB02377  (EXPT01672)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number73-40-5
WeightAverage: 150.1182
Monoisotopic: 150.041584775
Chemical FormulaC5H4N5O
InChI KeyIOJBSLDWMHFRAL-UHFFFAOYSA-N
InChI
InChI=1S/C5H4N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H3,6,8,9,10,11)
IUPAC Name
2-aminopurin-6-one
SMILES
NC1=Nc2ncnc2C(=O)N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassImidazopyrimidines
SubclassPurines and Purine Derivatives
Direct parentHypoxanthines
Alternative parentsPyrimidones; Primary Aromatic Amines; Imidazoles; Polyamines
Substituentspyrimidone; primary aromatic amine; pyrimidine; imidazole; azole; polyamine; primary amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one.
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 + 0.9948
Blood Brain Barrier + 0.9672
Caco-2 permeable - 0.643
P-glycoprotein substrate Non-substrate 0.6965
P-glycoprotein inhibitor I Non-inhibitor 0.9429
P-glycoprotein inhibitor II Non-inhibitor 0.9564
Renal organic cation transporter Non-inhibitor 0.8827
CYP450 2C9 substrate Non-substrate 0.8436
CYP450 2D6 substrate Non-substrate 0.8044
CYP450 3A4 substrate Non-substrate 0.6861
CYP450 1A2 substrate Non-inhibitor 0.7982
CYP450 2C9 substrate Non-inhibitor 0.9503
CYP450 2D6 substrate Non-inhibitor 0.9109
CYP450 2C19 substrate Non-inhibitor 0.8364
CYP450 3A4 substrate Non-inhibitor 0.8664
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9747
Ames test Non AMES toxic 0.591
Carcinogenicity Non-carcinogens 0.9624
Biodegradation Not ready biodegradable 0.9618
Rat acute toxicity 2.3231 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.961
hERG inhibition (predictor II) Non-inhibitor 0.9226
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point360 dec °CPhysProp
water solubility2080 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.91HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.53ALOGPS
logP-0.97ALOGPS
logP-1.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)6.91ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.55 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.24 m3·mol-1ChemAxon
Polarizability12.97 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Takeo Suzuki, Toshihide Nakanishi, “(2’-Amino-2’-deoxypentofuranosyl) guanine and process for producing same.” U.S. Patent US3987030, issued April, 1966.

US3987030
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00242
PubChem Compound764
PubChem Substance46507057
ChemSpider440297
ChEBI16235
ChEMBL
Therapeutic Targets DatabaseDNC000709
HETGUN
RxListhttp://www.rxlist.com/cgi/generic/thioguanine.htm
WikipediaGuanine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Purine nucleoside phosphorylase

Kind: protein

Organism: Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)

Pharmacological action: unknown

Components

Name UniProt ID Details
Purine nucleoside phosphorylase Q9X1T2 Details

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 2

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Purine nucleoside phosphorylase 2 P45563 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

4. Xanthine phosphoribosyltransferase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Xanthine phosphoribosyltransferase P0A9M5 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

5. GTP cyclohydrolase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
GTP cyclohydrolase 1 P30793 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18