4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile (CHEM044668)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 12:27:52 UTC
Update Date2016-11-09 01:23:11 UTC
Accession NumberCHEM044668
Identification
Common Name4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile
ClassSmall Molecule
DescriptionAn aminoquinoline that is 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline bearing additional cyano and methoxy substituents at positions 3 and 6 respectively.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-((2,4-Dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methyl-1-piperazinyl)propoxy)-3-quinolinecarbonitrileChEBI
SKI 606ChEBI
SKI-606ChEBI
BosulifHMDB
Chemical FormulaC26H29Cl2N5O3
Average Molecular Mass530.446 g/mol
Monoisotopic Mass529.165 g/mol
CAS Registry Number380843-75-4
IUPAC Name4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile
Traditional Namebosutinib
SMILESCOC1=CC(NC2=C(C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)C#N)=C(Cl)C=C1Cl
InChI IdentifierInChI=1S/C26H29Cl2N5O3/c1-32-6-8-33(9-7-32)5-4-10-36-25-13-21-18(11-24(25)35-3)26(17(15-29)16-30-21)31-22-14-23(34-2)20(28)12-19(22)27/h11-14,16H,4-10H2,1-3H3,(H,30,31)
InChI KeyUBPYILGKFZZVDX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct Parent4-aminoquinolines
Alternative Parents
Substituents
  • 4-aminoquinoline
  • Methoxyaniline
  • Aminophenyl ether
  • Anisole
  • 1,3-dichlorobenzene
  • Phenol ether
  • Aniline or substituted anilines
  • Methoxybenzene
  • Phenoxy compound
  • Alkyl aryl ether
  • N-alkylpiperazine
  • N-methylpiperazine
  • Aminopyridine
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Benzenoid
  • Aryl halide
  • Pyridine
  • Piperazine
  • Monocyclic benzene moiety
  • 1,4-diazinane
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Secondary amine
  • Ether
  • Carbonitrile
  • Nitrile
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0095 g/LALOGPS
logP4.87ALOGPS
logP4.09ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)15.48ChemAxon
pKa (Strongest Basic)8.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.88 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity142.12 m³·mol⁻¹ChemAxon
Polarizability56.02 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0092000000-68183c460c3cf8e08c01Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001l-1900080000-86f44693fc4098040447Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0200190000-83ef66b0c2abb8e9b17aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-2904330000-ee3bd613842432d7081bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08ml-9504200000-cb1df01119e14f605420Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0004090000-9c55d93dec61c52afac7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-009j-3009240000-c553208a343087042f35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1009000000-437a88d403cc82a326d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-1629a62e2e819fb0ea50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0300590000-c9854475db68bc576d9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c00-3401920000-079555df03b2d8c82b35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-6241b640c54394c3541cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-1108690000-356556ef25beb5e30365Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1106940000-950a9f00a3b8c654573bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06616
HMDB IDHMDB0240205
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBosutinib
Chemspider ID4486102
ChEBI ID39112
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18483306
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19039322
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19509264
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21148045
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21544849
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21680801
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21691746
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21700731
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21865346
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22031512
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22036634
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22037769
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22065400
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22179664
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22271876
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22311495
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22371878
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22425385
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22462037
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22471705
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22493660
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=22588706
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=22830347
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=22884766
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=22915985
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=22937303
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=22949154