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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:05:17 UTC
Update Date2021-09-26 23:02:39 UTC
HMDB IDHMDB0250931
Secondary Accession NumbersNone
Metabolite Identification
Common NameDefactinib
DescriptionDefactinib belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. Based on a literature review very few articles have been published on Defactinib. This compound has been identified in human blood as reported by (PMID: 31557052 ). Defactinib is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Defactinib is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
PF-04554878VS-6063DEFACTINIBChEMBL
N-Methyl-4-((4-(((3-methyl(methylsulfonyl)aminopyrazin-2-yl)methyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamideMeSH
Chemical FormulaC20H21F3N8O3S
Average Molecular Weight510.5
Monoisotopic Molecular Weight510.140942231
IUPAC NameN-methyl-4-{[4-({[3-(N-methylmethanesulfonamido)pyrazin-2-yl]methyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzamide
Traditional NameN-methyl-4-{[4-({[3-(N-methylmethanesulfonamido)pyrazin-2-yl]methyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzamide
CAS Registry NumberNot Available
SMILES
CNC(=O)C1=CC=C(NC2=NC=C(C(NCC3=C(N=CC=N3)N(C)S(C)(=O)=O)=N2)C(F)(F)F)C=C1
InChI Identifier
InChI=1S/C20H21F3N8O3S/c1-24-18(32)12-4-6-13(7-5-12)29-19-28-10-14(20(21,22)23)16(30-19)27-11-15-17(26-9-8-25-15)31(2)35(3,33)34/h4-10H,11H2,1-3H3,(H,24,32)(H2,27,28,29,30)
InChI KeyFWLMVFUGMHIOAA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzamides
Alternative Parents
Substituents
  • Benzamide
  • Benzoyl
  • Aniline or substituted anilines
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Organic sulfonic acid amide
  • Organosulfonic acid amide
  • Pyrazine
  • Pyrimidine
  • Imidolactam
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Alkyl halide
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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
logP2.39ALOGPS
logP0.75ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.63ChemAxon
pKa (Strongest Basic)4.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area142.1 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity123.28 m³·mol⁻¹ChemAxon
Polarizability46.05 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+204.73230932474
DeepCCS[M-H]-202.33630932474
DeepCCS[M-2H]-235.21930932474
DeepCCS[M+Na]+211.28530932474
AllCCS[M+H]+214.232859911
AllCCS[M+H-H2O]+212.432859911
AllCCS[M+NH4]+215.832859911
AllCCS[M+Na]+216.332859911
AllCCS[M-H]-205.732859911
AllCCS[M+Na-2H]-206.532859911
AllCCS[M+HCOO]-207.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DefactinibCNC(=O)C1=CC=C(NC2=NC=C(C(NCC3=C(N=CC=N3)N(C)S(C)(=O)=O)=N2)C(F)(F)F)C=C15453.3Standard polar33892256
DefactinibCNC(=O)C1=CC=C(NC2=NC=C(C(NCC3=C(N=CC=N3)N(C)S(C)(=O)=O)=N2)C(F)(F)F)C=C14097.3Standard non polar33892256
DefactinibCNC(=O)C1=CC=C(NC2=NC=C(C(NCC3=C(N=CC=N3)N(C)S(C)(=O)=O)=N2)C(F)(F)F)C=C14116.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Defactinib,1TMS,isomer #1CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)C=C1)[Si](C)(C)C3803.5Semi standard non polar33892256
Defactinib,1TMS,isomer #1CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)C=C1)[Si](C)(C)C3821.3Standard non polar33892256
Defactinib,1TMS,isomer #1CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)C=C1)[Si](C)(C)C5517.6Standard polar33892256
Defactinib,1TMS,isomer #2CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C)C=C13786.5Semi standard non polar33892256
Defactinib,1TMS,isomer #2CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C)C=C13749.0Standard non polar33892256
Defactinib,1TMS,isomer #2CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C)C=C15334.7Standard polar33892256
Defactinib,1TMS,isomer #3CNC(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)C=C13830.6Semi standard non polar33892256
Defactinib,1TMS,isomer #3CNC(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)C=C13869.1Standard non polar33892256
Defactinib,1TMS,isomer #3CNC(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)C=C15412.6Standard polar33892256
Defactinib,2TMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C)C=C1)[Si](C)(C)C3663.9Semi standard non polar33892256
Defactinib,2TMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C)C=C1)[Si](C)(C)C3845.5Standard non polar33892256
Defactinib,2TMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C)C=C1)[Si](C)(C)C4932.7Standard polar33892256
Defactinib,2TMS,isomer #2CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)C=C1)[Si](C)(C)C3690.7Semi standard non polar33892256
Defactinib,2TMS,isomer #2CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)C=C1)[Si](C)(C)C3964.9Standard non polar33892256
Defactinib,2TMS,isomer #2CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)C=C1)[Si](C)(C)C5020.9Standard polar33892256
Defactinib,2TMS,isomer #3CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)[Si](C)(C)C)C=C13712.4Semi standard non polar33892256
Defactinib,2TMS,isomer #3CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)[Si](C)(C)C)C=C13876.3Standard non polar33892256
Defactinib,2TMS,isomer #3CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)[Si](C)(C)C)C=C14796.9Standard polar33892256
Defactinib,3TMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)[Si](C)(C)C)C=C1)[Si](C)(C)C3623.8Semi standard non polar33892256
Defactinib,3TMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)[Si](C)(C)C)C=C1)[Si](C)(C)C3983.6Standard non polar33892256
Defactinib,3TMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C)=N2)[Si](C)(C)C)C=C1)[Si](C)(C)C4482.2Standard polar33892256
Defactinib,1TBDMS,isomer #1CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)C=C1)[Si](C)(C)C(C)(C)C4016.3Semi standard non polar33892256
Defactinib,1TBDMS,isomer #1CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)C=C1)[Si](C)(C)C(C)(C)C4053.0Standard non polar33892256
Defactinib,1TBDMS,isomer #1CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)C=C1)[Si](C)(C)C(C)(C)C5543.6Standard polar33892256
Defactinib,1TBDMS,isomer #2CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C(C)(C)C)C=C13968.2Semi standard non polar33892256
Defactinib,1TBDMS,isomer #2CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C(C)(C)C)C=C13971.9Standard non polar33892256
Defactinib,1TBDMS,isomer #2CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C(C)(C)C)C=C15279.2Standard polar33892256
Defactinib,1TBDMS,isomer #3CNC(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)C=C13999.7Semi standard non polar33892256
Defactinib,1TBDMS,isomer #3CNC(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)C=C14101.5Standard non polar33892256
Defactinib,1TBDMS,isomer #3CNC(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)C=C15381.1Standard polar33892256
Defactinib,2TBDMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C4041.4Semi standard non polar33892256
Defactinib,2TBDMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C4314.1Standard non polar33892256
Defactinib,2TBDMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C4976.4Standard polar33892256
Defactinib,2TBDMS,isomer #2CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)C=C1)[Si](C)(C)C(C)(C)C4062.6Semi standard non polar33892256
Defactinib,2TBDMS,isomer #2CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)C=C1)[Si](C)(C)C(C)(C)C4431.6Standard non polar33892256
Defactinib,2TBDMS,isomer #2CN(C(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)C=C1)[Si](C)(C)C(C)(C)C5081.1Standard polar33892256
Defactinib,2TBDMS,isomer #3CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)[Si](C)(C)C(C)(C)C)C=C14025.2Semi standard non polar33892256
Defactinib,2TBDMS,isomer #3CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)[Si](C)(C)C(C)(C)C)C=C14341.2Standard non polar33892256
Defactinib,2TBDMS,isomer #3CNC(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)[Si](C)(C)C(C)(C)C)C=C14803.7Standard polar33892256
Defactinib,3TBDMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C4099.9Semi standard non polar33892256
Defactinib,3TBDMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C4673.6Standard non polar33892256
Defactinib,3TBDMS,isomer #1CN(C(=O)C1=CC=C(N(C2=NC=C(C(F)(F)F)C(N(CC3=NC=CN=C3N(C)S(C)(=O)=O)[Si](C)(C)C(C)(C)C)=N2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C4582.9Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 10V, Positive-QTOFsplash10-03e9-0001950000-6c8868faa77ac183f8a92017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 20V, Positive-QTOFsplash10-01q9-1303900000-aab49419f0860c9b44dc2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 40V, Positive-QTOFsplash10-00dj-1789100000-0e42e9f80e49289a81122017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 10V, Negative-QTOFsplash10-0a4i-1101290000-c8b50d1326c9e91bff942017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 20V, Negative-QTOFsplash10-056r-8703910000-9f0ddab83511f58107ed2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 40V, Negative-QTOFsplash10-004i-9300000000-b759a7c7186cbbc3844f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 10V, Positive-QTOFsplash10-03di-0000390000-8cab74288a35a0d86b962021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 20V, Positive-QTOFsplash10-03e9-0001890000-25480435060aadca65b62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 40V, Positive-QTOFsplash10-0uk9-2717900000-7d682511fb3a86309c742021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 10V, Negative-QTOFsplash10-0a4i-0000090000-a99e22b91cf13ef9049b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 20V, Negative-QTOFsplash10-056r-9325850000-ac62e26f10d9256bd2162021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Defactinib 40V, Negative-QTOFsplash10-004i-9414110000-34bfa017b1fcf01990802021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12282
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID32695161
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]