(3S)-1-(1,3-BENZODIOXOL-5-YLMETHYL)-3-[4-(1H-IMIDAZOL-1-YL)PHENOXY]PIPERIDINE

Identification

Name
(3S)-1-(1,3-BENZODIOXOL-5-YLMETHYL)-3-[4-(1H-IMIDAZOL-1-YL)PHENOXY]PIPERIDINE
Accession Number
DB07011
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: 377.4363
Monoisotopic: 377.173941617
Chemical Formula
C22H23N3O3
InChI Key
HHOPJGKEAIIIDF-FQEVSTJZSA-N
InChI
InChI=1S/C22H23N3O3/c1-2-20(28-19-6-4-18(5-7-19)25-11-9-23-15-25)14-24(10-1)13-17-3-8-21-22(12-17)27-16-26-21/h3-9,11-12,15,20H,1-2,10,13-14,16H2/t20-/m0/s1
IUPAC Name
(3S)-1-(2H-1,3-benzodioxol-5-ylmethyl)-3-[4-(1H-imidazol-1-yl)phenoxy]piperidine
SMILES
[H][[email protected]@]1(CCCN(CC2=CC3=C(OCO3)C=C2)C1)OC1=CC=C(C=C1)N1C=CN=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
11740318
PubChem Substance
99443482
ChemSpider
9915025
BindingDB
50208484
ChEMBL
CHEMBL232827
HET
342
PDB Entries
2ort

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 Solubility0.0737 mg/mLALOGPS
logP3.16ALOGPS
logP2.84ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)8.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.75 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity116.08 m3·mol-1ChemAxon
Polarizability41.33 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9736
Blood Brain Barrier+0.9923
Caco-2 permeable+0.523
P-glycoprotein substrateSubstrate0.6448
P-glycoprotein inhibitor IInhibitor0.8097
P-glycoprotein inhibitor IIInhibitor0.8953
Renal organic cation transporterInhibitor0.606
CYP450 2C9 substrateNon-substrate0.8749
CYP450 2D6 substrateNon-substrate0.6653
CYP450 3A4 substrateSubstrate0.5266
CYP450 1A2 substrateInhibitor0.9323
CYP450 2C9 inhibitorInhibitor0.5827
CYP450 2D6 inhibitorInhibitor0.7863
CYP450 2C19 inhibitorInhibitor0.8529
CYP450 3A4 inhibitorInhibitor0.9191
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9737
Ames testNon AMES toxic0.5105
CarcinogenicityNon-carcinogens0.9383
BiodegradationNot ready biodegradable0.9875
Rat acute toxicity2.3545 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5185
hERG inhibition (predictor II)Inhibitor0.6037
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 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
Benzodioxoles / Phenoxy compounds / Phenol ethers / Aralkylamines / Alkyl aryl ethers / Piperidines / N-substituted imidazoles / Heteroaromatic compounds / Trialkylamines / Oxacyclic compounds
show 4 more
Substituents
1-phenylimidazole / Benzodioxole / Phenoxy compound / Phenol ether / Alkyl aryl ether / Aralkylamine / Monocyclic benzene moiety / N-substituted imidazole / Benzenoid / Piperidine
show 15 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