NAV

9-Deazaguanine

Identification

Generic Name
9-Deazaguanine
DrugBank Accession Number
DB04356
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 150.138
Monoisotopic: 150.054160834
Chemical Formula
C6H6N4O
Synonyms
Not Available
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHypoxanthine-guanine phosphoribosyltransferaseNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with 9-Deazaguanine.
AbametapirThe serum concentration of 9-Deazaguanine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of 9-Deazaguanine can be increased when combined with Abatacept.
AbirateroneThe serum concentration of 9-Deazaguanine can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with 9-Deazaguanine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolopyrimidines
Sub Class
Not Available
Direct Parent
Pyrrolopyrimidines
Alternative Parents
Pyrimidones / Aminopyrimidines and derivatives / Vinylogous amides / Pyrroles / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organic oxides
show 1 more
Substituents
Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyrrolopyrimidine (CHEBI:40431)
Affected organisms
Not Available

Chemical Identifiers

UNII
H2O1DD3CAN
CAS number
65996-58-9
InChI Key
FFYPRJYSJODFFD-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-amino-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one
SMILES
NC1=NC2=C(NC=C2)C(=O)N1

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 References
Not Available
PubChem Compound
100684
PubChem Substance
46508363
ChemSpider
90969
BindingDB
50108005
ChEMBL
CHEMBL367746
ZINC
ZINC000100004977
PDBe Ligand
9DG
PDB Entries
1fsg / 1il4 / 1q2r / 1q2s / 6d9r / 7nq4 / 8omr

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.03 mg/mLALOGPS
logP-0.48ALOGPS
logP-0.5Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.18Chemaxon
pKa (Strongest Basic)5.56Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area83.27 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity40.82 m3·mol-1Chemaxon
Polarizability13.96 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0zn9-3900000000-4a294a05cb58f8cf2d95
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-e0229262922d4d18ece9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1900000000-1c3a3d2d6a92f6154cd2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-1900000000-6cd4aa2622ca46e5d4e3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-4900000000-45a54223f68d22ecb350
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9000000000-a35462d729654981bb77
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-9400000000-ea45ab2ccb47ca742efe
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-128.522961
predicted
DarkChem Lite v0.1.0
[M-H]-127.76972
predicted
DeepCCS 1.0 (2019)
[M+H]+128.041661
predicted
DarkChem Lite v0.1.0
[M+H]+130.46352
predicted
DeepCCS 1.0 (2019)
[M+Na]+129.008461
predicted
DarkChem Lite v0.1.0
[M+Na]+139.51497
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Hypoxanthine-guanine phosphoribosyltransferase
Kind
Protein
Organism
Humans
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...
Gene Name
HPRT1
Uniprot ID
P00492
Uniprot Name
Hypoxanthine-guanine phosphoribosyltransferase
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Details1. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52