4-[(3S)-1-AZABICYCLO[2.2.2]OCT-3-YLAMINO]-3-(1H-BENZIMIDAZOL-2-YL)-6-CHLOROQUINOLIN-2(1H)-ONE

Identification

Name
4-[(3S)-1-AZABICYCLO[2.2.2]OCT-3-YLAMINO]-3-(1H-BENZIMIDAZOL-2-YL)-6-CHLOROQUINOLIN-2(1H)-ONE
Accession Number
DB06852
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
5K64W8EU3E
CAS number
Not Available
Weight
Average: 419.907
Monoisotopic: 419.151288058
Chemical Formula
C23H22ClN5O
InChI Key
MOVBBVMDHIRCTG-LJQANCHMSA-N
InChI
InChI=1S/C23H22ClN5O/c24-14-5-6-16-15(11-14)21(25-19-12-29-9-7-13(19)8-10-29)20(23(30)28-16)22-26-17-3-1-2-4-18(17)27-22/h1-6,11,13,19H,7-10,12H2,(H,26,27)(H2,25,28,30)/t19-/m1/s1
IUPAC Name
3-(1H-1,3-benzodiazol-2-yl)-6-chloro-4-{[(1S,3S,4s)-1-azabicyclo[2.2.2]octan-3-yl]amino}-1,2-dihydroquinolin-2-one
SMILES
[H][[email protected]@]12CC[[email protected]@](CC1)C[[email protected]@]2([H])NC1=C(C2=NC3=CC=CC=C3N2)C(=O)NC2=C1C=C(Cl)C=C2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USerine/threonine-protein kinase Chk1Not 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
11502647
PubChem Substance
99443323
ChemSpider
23270845
BindingDB
50185219
ChEMBL
CHEMBL377312
HET
12C
PDB Entries
2gdo

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 Solubility0.0266 mg/mLALOGPS
logP3.74ALOGPS
logP2.55ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)7.95ChemAxon
pKa (Strongest Basic)7.88ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.05 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity119.22 m3·mol-1ChemAxon
Polarizability44.19 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.7625
Caco-2 permeable-0.5993
P-glycoprotein substrateSubstrate0.7229
P-glycoprotein inhibitor IInhibitor0.6826
P-glycoprotein inhibitor IIInhibitor0.7397
Renal organic cation transporterInhibitor0.5517
CYP450 2C9 substrateNon-substrate0.8137
CYP450 2D6 substrateNon-substrate0.6135
CYP450 3A4 substrateSubstrate0.7138
CYP450 1A2 substrateInhibitor0.8026
CYP450 2C9 inhibitorInhibitor0.7338
CYP450 2D6 inhibitorNon-inhibitor0.5696
CYP450 2C19 inhibitorInhibitor0.8694
CYP450 3A4 inhibitorInhibitor0.5428
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.921
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.8925
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7326 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8178
hERG inhibition (predictor II)Inhibitor0.8659
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 hydroquinolones. These are compounds containing a hydrogenated quinoline bearing a ketone group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinolones and derivatives
Direct Parent
Hydroquinolones
Alternative Parents
4-aminoquinolines / Chloroquinolines / Hydroquinolines / Benzimidazoles / Quinuclidines / Aminopiperidines / Secondary alkylarylamines / Pyridinones / Aminopyridines and derivatives / Aryl chlorides
show 12 more
Substituents
Aminoquinoline / Dihydroquinolone / Chloroquinoline / 4-aminoquinoline / Haloquinoline / Dihydroquinoline / Benzimidazole / Quinuclidine / 3-aminopiperidine / Aminopyridine
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Serine/threonine-protein kinase which is required for checkpoint-mediated cell cycle arrest and activation of DNA repair in response to the presence of DNA damage or unreplicated DNA. May also nega...
Gene Name
CHEK1
Uniprot ID
O14757
Uniprot Name
Serine/threonine-protein kinase Chk1
Molecular Weight
54433.115 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 15:17 / Updated on December 01, 2017 15:42