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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:55:35 UTC
Update Date2021-09-26 23:02:30 UTC
HMDB IDHMDB0250818
Secondary Accession NumbersNone
Metabolite Identification
Common NameDabrafenib
DescriptionDabrafenib belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1. The biotransformation process of this drug is primarily regulated by _CYP2C8_ and _CYP3A4_ to form _hydroxy-debrafenib_. Dabrafenib is a moderately basic compound (based on its pKa). **Embryofetal Toxicity**: Can cause fetal harm. **Glucose-6-Phosphate Dehydrogenase Deficiency**: Closely monitor for hemolytic anemia . This compound has been identified in human blood as reported by (PMID: 31557052 ). Dabrafenib is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dabrafenib 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
GSK2118436aChEMBL
Chemical FormulaC23H20F3N5O2S2
Average Molecular Weight519.562
Monoisotopic Molecular Weight519.101050904
IUPAC NameN-{3-[5-(2-aminopyrimidin-4-yl)-2-tert-butyl-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzene-1-sulfonamide
Traditional NameN-{3-[5-(2-aminopyrimidin-4-yl)-2-tert-butyl-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide
CAS Registry NumberNot Available
SMILES
CC(C)(C)C1=NC(=C(S1)C1=NC(N)=NC=C1)C1=C(F)C(NS(=O)(=O)C2=C(F)C=CC=C2F)=CC=C1
InChI Identifier
InChI=1S/C23H20F3N5O2S2/c1-23(2,3)21-30-18(19(34-21)16-10-11-28-22(27)29-16)12-6-4-9-15(17(12)26)31-35(32,33)20-13(24)7-5-8-14(20)25/h4-11,31H,1-3H3,(H2,27,28,29)
InChI KeyBFSMGDJOXZAERB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassSulfanilides
Direct ParentSulfanilides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Sulfanilide
  • Benzenesulfonyl group
  • 2,4,5-trisubstituted 1,3-thiazole
  • Aminopyrimidine
  • Fluorobenzene
  • Halobenzene
  • Aryl fluoride
  • Aryl halide
  • Pyrimidine
  • Organosulfonic acid amide
  • Heteroaromatic compound
  • Azole
  • Aminosulfonyl compound
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Thiazole
  • Sulfonyl
  • Azacycle
  • Organoheterocyclic compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Primary amine
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
logP5.44ALOGPS
logP5.46ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)7.16ChemAxon
pKa (Strongest Basic)2.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.86 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127.51 m³·mol⁻¹ChemAxon
Polarizability49.71 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+207.50130932474
DeepCCS[M-H]-205.10630932474
DeepCCS[M-2H]-237.99130932474
DeepCCS[M+Na]+213.74130932474
AllCCS[M+H]+215.132859911
AllCCS[M+H-H2O]+213.232859911
AllCCS[M+NH4]+216.932859911
AllCCS[M+Na]+217.432859911
AllCCS[M-H]-202.632859911
AllCCS[M+Na-2H]-202.632859911
AllCCS[M+HCOO]-202.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DabrafenibCC(C)(C)C1=NC(=C(S1)C1=NC(N)=NC=C1)C1=C(F)C(NS(=O)(=O)C2=C(F)C=CC=C2F)=CC=C15221.0Standard polar33892256
DabrafenibCC(C)(C)C1=NC(=C(S1)C1=NC(N)=NC=C1)C1=C(F)C(NS(=O)(=O)C2=C(F)C=CC=C2F)=CC=C14001.4Standard non polar33892256
DabrafenibCC(C)(C)C1=NC(=C(S1)C1=NC(N)=NC=C1)C1=C(F)C(NS(=O)(=O)C2=C(F)C=CC=C2F)=CC=C13810.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dabrafenib,1TMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C)=N2)S13988.4Semi standard non polar33892256
Dabrafenib,1TMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C)=N2)S13603.1Standard non polar33892256
Dabrafenib,1TMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C)=N2)S15285.0Standard polar33892256
Dabrafenib,1TMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N)=N2)S13782.6Semi standard non polar33892256
Dabrafenib,1TMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N)=N2)S13710.8Standard non polar33892256
Dabrafenib,1TMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N)=N2)S15343.1Standard polar33892256
Dabrafenib,2TMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C)=N2)S13855.9Semi standard non polar33892256
Dabrafenib,2TMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C)=N2)S13738.0Standard non polar33892256
Dabrafenib,2TMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C)=N2)S14943.8Standard polar33892256
Dabrafenib,2TMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C)[Si](C)(C)C)=N2)S13886.2Semi standard non polar33892256
Dabrafenib,2TMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C)[Si](C)(C)C)=N2)S13680.4Standard non polar33892256
Dabrafenib,2TMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C)[Si](C)(C)C)=N2)S14764.3Standard polar33892256
Dabrafenib,3TMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C)[Si](C)(C)C)=N2)S13825.8Semi standard non polar33892256
Dabrafenib,3TMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C)[Si](C)(C)C)=N2)S13860.9Standard non polar33892256
Dabrafenib,3TMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C)[Si](C)(C)C)=N2)S14516.6Standard polar33892256
Dabrafenib,1TBDMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C(C)(C)C)=N2)S14150.9Semi standard non polar33892256
Dabrafenib,1TBDMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C(C)(C)C)=N2)S13806.3Standard non polar33892256
Dabrafenib,1TBDMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C(C)(C)C)=N2)S15225.3Standard polar33892256
Dabrafenib,1TBDMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N)=N2)S13972.2Semi standard non polar33892256
Dabrafenib,1TBDMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N)=N2)S13912.3Standard non polar33892256
Dabrafenib,1TBDMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N)=N2)S15283.7Standard polar33892256
Dabrafenib,2TBDMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C(C)(C)C)=N2)S14174.4Semi standard non polar33892256
Dabrafenib,2TBDMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C(C)(C)C)=N2)S14152.5Standard non polar33892256
Dabrafenib,2TBDMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N[Si](C)(C)C(C)(C)C)=N2)S14936.2Standard polar33892256
Dabrafenib,2TBDMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)S14220.4Semi standard non polar33892256
Dabrafenib,2TBDMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)S14063.6Standard non polar33892256
Dabrafenib,2TBDMS,isomer #2CC(C)(C)C1=NC(C2=CC=CC(NS(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)S14745.5Standard polar33892256
Dabrafenib,3TBDMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)S14264.9Semi standard non polar33892256
Dabrafenib,3TBDMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)S14446.7Standard non polar33892256
Dabrafenib,3TBDMS,isomer #1CC(C)(C)C1=NC(C2=CC=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C3=C(F)C=CC=C3F)=C2F)=C(C2=CC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)S14563.1Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 10V, Positive-QTOFsplash10-00di-0101090000-3d822f3070e12c0a25de2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 20V, Positive-QTOFsplash10-00fu-6401490000-7f293c68542d528176542017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 40V, Positive-QTOFsplash10-00mo-9206000000-fc4c07b08fb022fe73ff2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 10V, Negative-QTOFsplash10-014i-0000190000-bf7bb6ec6a8a3fbfe30f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 20V, Negative-QTOFsplash10-016r-2002970000-1a03623cb78c227c84122017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 40V, Negative-QTOFsplash10-03dl-5906300000-8683f0d4d61c4bc7ddfb2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 10V, Positive-QTOFsplash10-00di-0000090000-6314d347a91b074cccf72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 20V, Positive-QTOFsplash10-00di-0100090000-8dbd5e99b14262f5c8d32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 40V, Positive-QTOFsplash10-0np0-3058920000-39ae17e02796c831bd0b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 10V, Negative-QTOFsplash10-014i-0000090000-26ac25d8f7a87604ee692021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 20V, Negative-QTOFsplash10-014i-0000090000-b80693a60154d356e3d52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dabrafenib 40V, Negative-QTOFsplash10-03g0-0146910000-8dd9b33b95a971a7ae662021-10-12Wishart 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 IDDB08912
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDabrafenib
METLIN IDNot Available
PubChem Compound44462760
PDB IDNot Available
ChEBI ID75045
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 ]