Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-10-31 16:02:31 UTC
Update Date2022-03-07 03:18:13 UTC
HMDB IDHMDB0240206
Secondary Accession NumbersNone
Metabolite Identification
Common NameBafetinib
DescriptionBafetinib is a tyrosine kinase inhibitor used to treat chronic myelogenous leukemia (CML), a cancer characterized by increased and unregulated growth of white blood cells in the bone marrow and the accumulation of these cells in the blood. Bafetinib is able to bind ABL with greater affinity than Imatinib (25-55 times more potent). It is therefore administered to patients with Imatinib resistance. Notably, Bafetinib is ineffective against the T315I mutation in BCR-ABL, and further research is necessary.
Structure
Data?1563892728
Synonyms
ValueSource
INNO-406MeSH
N-(3-((4,5'-Bipyrimidin)-2-ylamino)-4-methylphenyl)-4-(((3S)-3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)benzamideMeSH
NS-187inno-406BAFETINIBChEMBL, HMDB
Chemical FormulaC30H31F3N8O
Average Molecular Weight576.6153
Monoisotopic Molecular Weight576.257292269
IUPAC NameN-[3-({[4,5'-bipyrimidine]-2-yl}amino)-4-methylphenyl]-4-{[(3S)-3-(dimethylamino)pyrrolidin-1-yl]methyl}-3-(trifluoromethyl)benzamide
Traditional NameN-(3-{[4,5'-bipyrimidine]-2-ylamino}-4-methylphenyl)-4-{[(3S)-3-(dimethylamino)pyrrolidin-1-yl]methyl}-3-(trifluoromethyl)benzamide
CAS Registry Number859212-16-1
SMILES
CN(C)[C@H]1CCN(CC2=C(C=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CN=C3)=C(C)C=C2)C(F)(F)F)C1
InChI Identifier
InChI=1S/C30H31F3N8O/c1-19-4-7-23(13-27(19)39-29-36-10-8-26(38-29)22-14-34-18-35-15-22)37-28(42)20-5-6-21(25(12-20)30(31,32)33)16-41-11-9-24(17-41)40(2)3/h4-8,10,12-15,18,24H,9,11,16-17H2,1-3H3,(H,37,42)(H,36,38,39)/t24-/m0/s1
InChI KeyZGBAJMQHJDFTQJ-DEOSSOPVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentBenzanilides
Alternative Parents
Substituents
  • Benzanilide
  • Bipyrimidine
  • Trifluoromethylbenzene
  • Benzamide
  • Benzoic acid or derivatives
  • Diaminotoluene
  • Benzoyl
  • Benzylamine
  • Phenylmethylamine
  • Aniline or substituted anilines
  • Aralkylamine
  • Toluene
  • Aminopyrimidine
  • N-alkylpyrrolidine
  • Pyrimidine
  • Pyrrolidine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Amine
  • Organohalogen compound
  • Organic oxide
  • Alkyl halide
  • Alkyl fluoride
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organofluoride
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP3.52ALOGPS
logP4.67ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)12.63ChemAxon
pKa (Strongest Basic)9.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.17 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity158.26 m³·mol⁻¹ChemAxon
Polarizability59.22 ųChemAxon
Number of Rings5ChemAxon
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]+236.18531661259
AllCCS[M-H]-222.431661259
DeepCCS[M+H]+229.58330932474
DeepCCS[M-H]-227.27630932474
DeepCCS[M-2H]-260.51530932474
DeepCCS[M+Na]+235.39430932474
AllCCS[M+H]+236.232859911
AllCCS[M+H-H2O]+234.932859911
AllCCS[M+NH4]+237.332859911
AllCCS[M+Na]+237.632859911
AllCCS[M-H]-222.432859911
AllCCS[M+Na-2H]-223.932859911
AllCCS[M+HCOO]-225.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BafetinibCN(C)[C@H]1CCN(CC2=C(C=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CN=C3)=C(C)C=C2)C(F)(F)F)C15346.3Standard polar33892256
BafetinibCN(C)[C@H]1CCN(CC2=C(C=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CN=C3)=C(C)C=C2)C(F)(F)F)C14626.7Standard non polar33892256
BafetinibCN(C)[C@H]1CCN(CC2=C(C=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CN=C3)=C(C)C=C2)C(F)(F)F)C14848.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bafetinib,1TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CN=CN=C2)=N14329.7Semi standard non polar33892256
Bafetinib,1TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CN=CN=C2)=N13877.4Standard non polar33892256
Bafetinib,1TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CN=CN=C2)=N15734.8Standard polar33892256
Bafetinib,1TMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C4399.2Semi standard non polar33892256
Bafetinib,1TMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C4097.6Standard non polar33892256
Bafetinib,1TMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C5584.7Standard polar33892256
Bafetinib,2TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C4181.0Semi standard non polar33892256
Bafetinib,2TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C3843.0Standard non polar33892256
Bafetinib,2TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C5208.1Standard polar33892256
Bafetinib,1TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CN=CN=C2)=N14507.6Semi standard non polar33892256
Bafetinib,1TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CN=CN=C2)=N14053.1Standard non polar33892256
Bafetinib,1TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CN=CN=C2)=N15746.4Standard polar33892256
Bafetinib,1TBDMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C(C)(C)C4558.0Semi standard non polar33892256
Bafetinib,1TBDMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C(C)(C)C4265.0Standard non polar33892256
Bafetinib,1TBDMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C(C)(C)C5579.2Standard polar33892256
Bafetinib,2TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C(C)(C)C)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C(C)(C)C4498.4Semi standard non polar33892256
Bafetinib,2TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C(C)(C)C)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C(C)(C)C4176.5Standard non polar33892256
Bafetinib,2TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CC[C@H](N(C)C)C3)C(C(F)(F)F)=C2)[Si](C)(C)C(C)(C)C)C=C1N(C1=NC=CC(C2=CN=CN=C2)=N1)[Si](C)(C)C(C)(C)C5246.0Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 10V, Positive-QTOFsplash10-004i-0040390000-e87c0acc07a42ddb443c2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 20V, Positive-QTOFsplash10-03g0-0390440000-52ebb49e5e879f1cfebd2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 40V, Positive-QTOFsplash10-01ri-2890100000-c2313e4460d8512f01cb2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 10V, Negative-QTOFsplash10-004i-0100090000-2c0d7c69c6c6f0ca547a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 20V, Negative-QTOFsplash10-0200-3442290000-90d7133777a888520cb72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 40V, Negative-QTOFsplash10-0100-9550010000-798bb3e96f2f8f62118f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 10V, Positive-QTOFsplash10-004i-0000090000-962a71e30e420965bb572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 20V, Positive-QTOFsplash10-03fr-0810290000-c263f269687456bf7f482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 40V, Positive-QTOFsplash10-000i-4930150000-7ddeaa97cc30f1654a0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 10V, Negative-QTOFsplash10-004i-0000090000-85853253a5e2c3faaac82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 20V, Negative-QTOFsplash10-004i-0000390000-e4f8bbfc295433ff8c432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bafetinib 40V, Negative-QTOFsplash10-00di-0020980000-6caa32826aac550f9eec2021-09-23Wishart 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 IDDB11851
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9562515
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBafetinib
METLIN IDNot Available
PubChem Compound11387605
PDB IDNot Available
ChEBI IDNot Available
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