NAV

4-(1,3-BENZODIOXOL-5-YLOXY)-2-[4-(1H-IMIDAZOL-1-YL)PHENOXY]-6-METHYLPYRIMIDINE

Identification

Generic Name
4-(1,3-BENZODIOXOL-5-YLOXY)-2-[4-(1H-IMIDAZOL-1-YL)PHENOXY]-6-METHYLPYRIMIDINE
DrugBank Accession Number
DB07029
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 388.3761
Monoisotopic: 388.11715502
Chemical Formula
C21H16N4O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, inducibleNot 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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylimidazoles. These are polycyclic aromatic compounds containing a benzene ring linked to an imidazole ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Imidazoles
Direct Parent
Phenylimidazoles
Alternative Parents
Diarylethers / Benzodioxoles / Phenoxy compounds / Phenol ethers / Pyrimidines and pyrimidine derivatives / N-substituted imidazoles / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Acetals
show 3 more
Substituents
1-phenylimidazole / Acetal / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzodioxole / Diaryl ether / Ether / Heteroaromatic compound / Hydrocarbon derivative
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QQBNDYARFVOEGW-UHFFFAOYSA-N
InChI
InChI=1S/C21H16N4O4/c1-14-10-20(28-17-6-7-18-19(11-17)27-13-26-18)24-21(23-14)29-16-4-2-15(3-5-16)25-9-8-22-12-25/h2-12H,13H2,1H3
IUPAC Name
4-(2H-1,3-benzodioxol-5-yloxy)-2-[4-(1H-imidazol-1-yl)phenoxy]-6-methylpyrimidine
SMILES
CC1=NC(OC2=CC=C(C=C2)N2C=CN=C2)=NC(OC2=CC3=C(OCO3)C=C2)=C1

References

General References
Not Available
PubChem Compound
10157080
PubChem Substance
99443500
ChemSpider
8332588
BindingDB
50207104
ChEMBL
CHEMBL390674
ZINC
ZINC000016052317
PDBe Ligand
391
PDB Entries
2ors

Clinical Trials

Clinical Trials
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 Solubility0.037 mg/mLALOGPS
logP3.79ALOGPS
logP3.84Chemaxon
logS-4ALOGPS
pKa (Strongest Basic)6.06Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area80.52 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity113.77 m3·mol-1Chemaxon
Polarizability38.46 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9902
Blood Brain Barrier+0.9868
Caco-2 permeable+0.508
P-glycoprotein substrateNon-substrate0.7655
P-glycoprotein inhibitor INon-inhibitor0.5507
P-glycoprotein inhibitor IINon-inhibitor0.7168
Renal organic cation transporterNon-inhibitor0.8411
CYP450 2C9 substrateNon-substrate0.788
CYP450 2D6 substrateNon-substrate0.8386
CYP450 3A4 substrateSubstrate0.5636
CYP450 1A2 substrateInhibitor0.586
CYP450 2C9 inhibitorNon-inhibitor0.5345
CYP450 2D6 inhibitorNon-inhibitor0.5144
CYP450 2C19 inhibitorInhibitor0.7095
CYP450 3A4 inhibitorInhibitor0.7573
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7594
Ames testAMES toxic0.5539
CarcinogenicityNon-carcinogens0.8915
BiodegradationNot ready biodegradable0.6669
Rat acute toxicity2.1184 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9695
hERG inhibition (predictor II)Non-inhibitor0.8434
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-MSsplash10-114i-4169000000-81470ebb87a6bf5c2a6c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-1f61edaadefcedd3f3c2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-53cd76c2cf5de7b12311
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-07cefc65b1d6825b4959
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06ri-0009000000-5d142045a63ea670ce73
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1319000000-2a6adfab838461c7cbab
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01pc-0019000000-5aafe6e69e5476f9a3f2
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]-187.29692
predicted
DeepCCS 1.0 (2019)
[M+H]+189.65492
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.07549
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Nitric oxide synthase, inducible
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
Molecular Weight
131116.3 Da
References
  1. 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]

Drug created at September 15, 2010 21:18 / Updated at June 12, 2020 16:52