Identification
Name9-Deazaguanine
Accession NumberDB04356  (EXPT00356)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIINot Available
CAS numberNot Available
WeightAverage: 150.138
Monoisotopic: 150.054160834
Chemical FormulaC6H6N4O
InChI KeyFFYPRJYSJODFFD-UHFFFAOYSA-N
InChI
InChI=1S/C6H6N4O/c7-6-9-3-1-2-8-4(3)5(11)10-6/h1-2,8H,(H3,7,9,10,11)
IUPAC Name
2-imino-1H,2H,5H-pyrrolo[3,2-d]pyrimidin-4-ol
SMILES
OC1=NC(=N)NC2=C1NC=C2
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Hypoxanthine-guanine phosphoribosyltransferaseProteinunknownNot AvailableHumanP00492 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis Reference

Arthur J. Elliott, David A. Walsh, "Process for the preparation of 9-deazaguanine derivatives." U.S. Patent US5650511, issued September, 1990.

US5650511
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.01 mg/mLALOGPS
logP-0.38ALOGPS
logP0.19ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.95ChemAxon
pKa (Strongest Basic)5.99ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area84.26 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.41 m3·mol-1ChemAxon
Polarizability13.96 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9845
Blood Brain Barrier+0.9509
Caco-2 permeable-0.5468
P-glycoprotein substrateNon-substrate0.6654
P-glycoprotein inhibitor INon-inhibitor0.9562
P-glycoprotein inhibitor IINon-inhibitor0.9895
Renal organic cation transporterNon-inhibitor0.8841
CYP450 2C9 substrateNon-substrate0.8628
CYP450 2D6 substrateNon-substrate0.7741
CYP450 3A4 substrateNon-substrate0.6764
CYP450 1A2 substrateNon-inhibitor0.7562
CYP450 2C9 inhibitorNon-inhibitor0.9495
CYP450 2D6 inhibitorNon-inhibitor0.8952
CYP450 2C19 inhibitorNon-inhibitor0.8771
CYP450 3A4 inhibitorNon-inhibitor0.9421
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.979
Ames testNon AMES toxic0.6878
CarcinogenicityNon-carcinogens0.9658
BiodegradationNot ready biodegradable0.972
Rat acute toxicity2.3603 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9505
hERG inhibition (predictor II)Non-inhibitor0.9373
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyrrolopyrimidines
Direct ParentPyrrolopyrimidines
Alternative ParentsPyrimidones / Aminopyrimidines and derivatives / Primary aromatic amines / Vinylogous amides / Pyrroles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organic oxides
SubstituentsPyrrolopyrimidine / Aminopyrimidine / Pyrimidone / Primary aromatic amine / Pyrimidine / Pyrrole / Vinylogous amide / Heteroaromatic compound / Azacycle / Hydrocarbon derivative
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorspyrrolopyrimidine (CHEBI:40431 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein homodimerization activity
Specific Function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:
HPRT1
Uniprot ID:
P00492
Molecular Weight:
24579.155 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 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Drug created on June 13, 2005 07:24 / Updated on June 11, 2017 20:55