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

Identification

Name
4-(1,3-BENZODIOXOL-5-YLOXY)-2-[4-(1H-IMIDAZOL-1-YL)PHENOXY]-6-METHYLPYRIMIDINE
Accession Number
DB07029
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 388.3761
Monoisotopic: 388.11715502
Chemical Formula
C21H16N4O4
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, inducibleNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
10157080
PubChem Substance
99443500
ChemSpider
8332588
BindingDB
50207104
ChEMBL
CHEMBL390674
HET
391
PDB Entries
2ors

Clinical Trials

Clinical Trials
Not Available

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
logP3.22ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)6.43ChemAxon
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Diaryl ether / 1-phenylimidazole / Benzodioxole / Phenoxy compound / Phenol ether / Monocyclic benzene moiety / N-substituted imidazole / Pyrimidine / Benzenoid / Heteroaromatic compound
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:18 / Updated on December 01, 2017 15:45