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

Identification

Name
4-(1,3-BENZODIOXOL-5-YLOXY)-2-[4-(1H-IMIDAZOL-1-YL)PHENOXY]PYRIMIDINE
Accession Number
DB07008
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: 374.3496
Monoisotopic: 374.101504956
Chemical Formula
C20H14N4O4
InChI Key
XPXGYINSBORUMM-UHFFFAOYSA-N
InChI
InChI=1S/C20H14N4O4/c1-3-15(4-2-14(1)24-10-9-21-12-24)28-20-22-8-7-19(23-20)27-16-5-6-17-18(11-16)26-13-25-17/h1-12H,13H2
IUPAC Name
4-(2H-1,3-benzodioxol-5-yloxy)-2-[4-(1H-imidazol-1-yl)phenoxy]pyrimidine
SMILES
C1OC2=C(O1)C=C(OC1=CC=NC(OC3=CC=C(C=C3)N3C=CN=C3)=N1)C=C2

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
9969613
PubChem Substance
99443479
ChemSpider
8145205
BindingDB
50207101
ChEMBL
CHEMBL243978
HET
333
PDB Entries
2orr

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 Solubility0.0727 mg/mLALOGPS
logP3.5ALOGPS
logP3.05ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)6.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area80.52 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.18 m3·mol-1ChemAxon
Polarizability36.27 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9831
Blood Brain Barrier+0.9923
Caco-2 permeable-0.5214
P-glycoprotein substrateNon-substrate0.8203
P-glycoprotein inhibitor INon-inhibitor0.5879
P-glycoprotein inhibitor IINon-inhibitor0.6464
Renal organic cation transporterNon-inhibitor0.8267
CYP450 2C9 substrateNon-substrate0.8417
CYP450 2D6 substrateNon-substrate0.8321
CYP450 3A4 substrateSubstrate0.5233
CYP450 1A2 substrateInhibitor0.5848
CYP450 2C9 inhibitorNon-inhibitor0.587
CYP450 2D6 inhibitorInhibitor0.5
CYP450 2C19 inhibitorInhibitor0.6763
CYP450 3A4 inhibitorInhibitor0.6723
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6843
Ames testAMES toxic0.5243
CarcinogenicityNon-carcinogens0.9015
BiodegradationNot ready biodegradable0.6142
Rat acute toxicity2.1323 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9733
hERG inhibition (predictor II)Non-inhibitor0.8518
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 15:44