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Identification
Name8-azaguanine
Accession NumberDB01667  (EXPT00603)
Typesmall molecule
Groupsexperimental
Description

One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
AzaguanineNot AvailableNot Available
Azaguanine-8Not AvailableNot Available
GuanazolNot AvailableNot Available
PathocidinNot AvailableNot Available
PathocidineNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number134-58-7
WeightAverage: 152.1142
Monoisotopic: 152.04465878
Chemical FormulaC4H4N6O
InChI KeyInChIKey=LPXQRXLUHJKZIE-UHFFFAOYSA-N
InChI
InChI=1S/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11)
IUPAC Name
5-amino-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol
SMILES
NC1=NC2=C(NN=N2)C(O)=N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassTriazolopyrimidines
SubclassNot Available
Direct parentTriazolopyrimidines
Alternative parentsPyrimidines and Pyrimidine Derivatives; Primary Aromatic Amines; Triazoles; Polyamines
Substituentspyrimidine; primary aromatic amine; 1,2,3-triazole; azole; polyamine; amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the triazolopyrimidines. These are polycyclic aromatic compounds containing triazole ring fused to a pyrimidine ring.
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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9848
Blood Brain Barrier + 0.9379
Caco-2 permeable - 0.5611
P-glycoprotein substrate Non-substrate 0.7336
P-glycoprotein inhibitor I Non-inhibitor 0.9648
P-glycoprotein inhibitor II Non-inhibitor 0.9962
Renal organic cation transporter Non-inhibitor 0.9382
CYP450 2C9 substrate Non-substrate 0.8774
CYP450 2D6 substrate Non-substrate 0.8279
CYP450 3A4 substrate Non-substrate 0.6789
CYP450 1A2 substrate Non-inhibitor 0.8259
CYP450 2C9 substrate Non-inhibitor 0.8776
CYP450 2D6 substrate Non-inhibitor 0.8597
CYP450 2C19 substrate Non-inhibitor 0.8702
CYP450 3A4 substrate Non-inhibitor 0.834
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9635
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.9131
Biodegradation Not ready biodegradable 0.9907
Rat acute toxicity 2.4904 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.784
hERG inhibition (predictor II) Non-inhibitor 0.9205
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point300 °CPhysProp
water solubilityInsolubleNot Available
logP-0.71HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility5.66e+00 g/lALOGPS
logP-0.87ALOGPS
logP-0.16ChemAxon
logS-1.4ALOGPS
pKa (strongest acidic)7.89ChemAxon
pKa (strongest basic)0.05ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count3ChemAxon
polar surface area113.6ChemAxon
rotatable bond count0ChemAxon
refractivity39.24ChemAxon
polarizability12.62ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Tong, George L.; Lee, William W.; Goodman, Leon; Frederiksen, Sune (1965). “Synthesis of some 2′-deoxyribosides of 8-azaadenine”. Archives of Biochemistry and Biophysics (University of California: Elsevier) 112 (1): 76. http://dx.doi.org/10.1016/0003-9861(65)90012-3
  2. Michels AW, Ostrov DA, Zhang L, Nakayama M, Fuse M, McDaniel K, Roep BO, Gottlieb PA, Atkinson MA, Eisenbarth GS: Structure-based selection of small molecules to alter allele-specific MHC class II antigen presentation. J Immunol. 2011 Dec 1;187(11):5921-30. Epub 2011 Oct 31. Pubmed
External Links
ResourceLink
BindingDB50200096
ChEBI40862
ChEMBL
HETAZG
Wikipedia8-Azaguanine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. 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

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15