vemurafenib (CHEM045661)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:33:51 UTC
Update Date2016-11-09 01:23:23 UTC
Accession NumberCHEM045661
Identification
Common Namevemurafenib
ClassSmall Molecule
DescriptionA pyrrolopyridine that is 1H-pyrrolo[2,3-b]pyridine which is substituted at position 5 by a p-chlorophenyl group and at positions 3 by a 3-amino-2,6-difluorobenzoyl group, the amino group of which has undergone formal condensation with propane-1-sulfonic acid to give the corresponding sulfonamide. An inhibitor of BRAF and other kinases.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
VemurafenibumChEBI
ZelborafChEBI
Chemical FormulaC23H18ClF2N3O3S
Average Molecular Mass489.922 g/mol
Monoisotopic Mass489.073 g/mol
CAS Registry Number1029872-54-5
IUPAC NameN-{3-[5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluorophenyl}propane-1-sulfonamide
Traditional Namevemurafenib
SMILESCCCS(=O)(=O)NC1=C(F)C(C(=O)C2=CNC3=NC=C(C=C23)C2=CC=C(Cl)C=C2)=C(F)C=C1
InChI IdentifierInChI=1S/C23H18ClF2N3O3S/c1-2-9-33(31,32)29-19-8-7-18(25)20(21(19)26)22(30)17-12-28-23-16(17)10-14(11-27-23)13-3-5-15(24)6-4-13/h3-8,10-12,29H,2,9H2,1H3,(H,27,28)
InChI KeyGPXBXXGIAQBQNI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-phenylketones
Alternative Parents
Substituents
  • Aryl-phenylketone
  • 3-phenylpyridine
  • Sulfanilide
  • Pyrrolopyridine
  • Benzoyl
  • Halobenzene
  • Fluorobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Pyridine
  • Aryl fluoride
  • Organosulfonic acid amide
  • Organic sulfonic acid amide
  • Substituted pyrrole
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Vinylogous halide
  • Aminosulfonyl compound
  • Pyrrole
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Solubility0.00036 g/LALOGPS
logP4.95ALOGPS
logP4.62ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)7.17ChemAxon
pKa (Strongest Basic)3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.92 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity121.97 m³·mol⁻¹ChemAxon
Polarizability48.1 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9212300000-fbdbb92088febd3eda6bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0024900000-4911e6c7ad52fd2c2896Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0281900000-e08321c7aa665a4f4c73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-6494400000-4ea2fc0a4cbd6d24d3ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1190000000-fd8302ac94aec0904dc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0020900000-de3f93933bd01bde416fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002k-0142900000-fa7a706c558c555f7315Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-4980500000-02de2d40bd79e37e37f1Spectrum
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 IDDB08881
HMDB IDHMDB0259779
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkVemurafenib
Chemspider ID24747352
ChEBI ID63637
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=21609436
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21639808
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22028422
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22037033
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22083257
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22180495