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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-10-29 03:19:51 UTC
Update Date2019-07-23 14:38:48 UTC
HMDB IDHMDB0240205
Secondary Accession NumbersNone
Metabolite Identification
Common NameBosutinib
DescriptionBosutinib, also known as SKI 606, 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. In humans, bosutinib is involved in the bosutinib inhibition of bcr-abl pathway. Bosutinib is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Bosutinib.
Structure
Data?1563892728
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 Weight530.446
Monoisotopic Molecular Weight529.164745233
IUPAC Name4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile
Traditional Namebosutinib
CAS Registry Number380843-75-4
SMILES
COC1=CC(NC2=C(C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)C#N)=C(Cl)C=C1Cl
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
DispositionNot Available
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+221.11331661259
AllCCS[M-H]-214.43231661259
DeepCCS[M-2H]-246.78130932474
DeepCCS[M+Na]+223.04930932474
AllCCS[M+H]+221.132859911
AllCCS[M+H-H2O]+219.432859911
AllCCS[M+NH4]+222.632859911
AllCCS[M+Na]+223.132859911
AllCCS[M-H]-214.432859911
AllCCS[M+Na-2H]-215.332859911
AllCCS[M+HCOO]-216.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BosutinibCOC1=CC(NC2=C(C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)C#N)=C(Cl)C=C1Cl5145.5Standard polar33892256
BosutinibCOC1=CC(NC2=C(C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)C#N)=C(Cl)C=C1Cl3961.8Standard non polar33892256
BosutinibCOC1=CC(NC2=C(C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)C#N)=C(Cl)C=C1Cl4445.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bosutinib,1TMS,isomer #1COC1=CC(N(C2=C(C#N)C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)[Si](C)(C)C)=C(Cl)C=C1Cl4083.6Semi standard non polar33892256
Bosutinib,1TMS,isomer #1COC1=CC(N(C2=C(C#N)C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)[Si](C)(C)C)=C(Cl)C=C1Cl3918.8Standard non polar33892256
Bosutinib,1TMS,isomer #1COC1=CC(N(C2=C(C#N)C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)[Si](C)(C)C)=C(Cl)C=C1Cl5712.6Standard polar33892256
Bosutinib,1TBDMS,isomer #1COC1=CC(N(C2=C(C#N)C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1Cl4240.0Semi standard non polar33892256
Bosutinib,1TBDMS,isomer #1COC1=CC(N(C2=C(C#N)C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1Cl4102.1Standard non polar33892256
Bosutinib,1TBDMS,isomer #1COC1=CC(N(C2=C(C#N)C=NC3=CC(OCCCN4CCN(C)CC4)=C(OC)C=C23)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1Cl5691.8Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Bosutinib , positive-QTOFsplash10-014i-0092000000-68183c460c3cf8e08c012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bosutinib , positive-QTOFsplash10-001l-1900080000-86f44693fc40980404472017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 10V, Positive-QTOFsplash10-001i-0200190000-83ef66b0c2abb8e9b17a2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 20V, Positive-QTOFsplash10-03dl-2904330000-ee3bd613842432d7081b2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 40V, Positive-QTOFsplash10-08ml-9504200000-cb1df01119e14f6054202017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 10V, Negative-QTOFsplash10-004i-0004090000-9c55d93dec61c52afac72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 20V, Negative-QTOFsplash10-009j-3009240000-c553208a343087042f352017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 40V, Negative-QTOFsplash10-00di-1009000000-437a88d403cc82a326d32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 10V, Positive-QTOFsplash10-001i-0000090000-1629a62e2e819fb0ea502021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 20V, Positive-QTOFsplash10-001i-0300590000-c9854475db68bc576d9c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 40V, Positive-QTOFsplash10-0c00-3401920000-079555df03b2d8c82b352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 10V, Negative-QTOFsplash10-004i-0000090000-6241b640c54394c3541c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 20V, Negative-QTOFsplash10-004r-1108690000-356556ef25beb5e303652021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bosutinib 40V, Negative-QTOFsplash10-00di-1106940000-950a9f00a3b8c654573b2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06616
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4486102
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBosutinib
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID39112
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available