You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:04:56 UTC
Update Date2019-07-23 07:15:16 UTC
HMDB IDHMDB0060873
Secondary Accession Numbers
  • HMDB60873
Metabolite Identification
Common NameSorafenib N-oxide
DescriptionSorafenib N-oxide, also known as sorafenib or nexavar, belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. Sorafenib N-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). sorafenib N-oxide can be biosynthesized from sorafenib through the action of the enzyme cytochrome P450 3A4. In humans, sorafenib N-oxide is involved in sorafenib metabolism pathway.
Structure
Data?1563866116
Synonyms
ValueSource
NexavarHMDB
4-(4-(3-(4-Chloro-3-trifluoromethylphenyl)ureido)phenoxy)pyridine-2-carboxyllic acid methyamide-4-methylbenzenesulfonateHMDB
SorafenibHMDB
Sorafenib tosylateHMDB
4-(4-(3-(4-Chloro-3-trifluoromethylphenyl)ureido)phenoxy)pyridine-2-carboxylic acid methyamide-4-methylbenzenesulfonateMeSH
Sorafenib N oxideMeSH
Chemical FormulaC21H16ClF3N4O4
Average Molecular Weight480.824
Monoisotopic Molecular Weight480.081217342
IUPAC Name4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-2-(methylcarbamoyl)pyridin-1-ium-1-olate
Traditional Name4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-2-(methylcarbamoyl)pyridin-1-ium-1-olate
CAS Registry NumberNot Available
SMILES
CNC(=O)C1=[N+]([O-])C=CC(OC2=CC=C(NC(=O)NC3=CC=C(Cl)C(=C3)C(F)(F)F)C=C2)=C1
InChI Identifier
InChI=1S/C21H16ClF3N4O4/c1-26-19(30)18-11-15(8-9-29(18)32)33-14-5-2-12(3-6-14)27-20(31)28-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,27,28,31)
InChI KeyBQAZCCVUZDIZDC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentDiarylethers
Alternative Parents
Substituents
  • Diaryl ether
  • N-phenylurea
  • Trifluoromethylbenzene
  • Pyridine carboxylic acid or derivatives
  • 2-heteroaryl carboxamide
  • Phenoxy compound
  • Phenol ether
  • Chlorobenzene
  • Halobenzene
  • Benzenoid
  • Pyridinium
  • Pyridine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Urea
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carbonic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Organic zwitterion
  • Organopnictogen compound
  • Alkyl halide
  • Organic nitrogen compound
  • Alkyl fluoride
  • Organohalogen compound
  • Organochloride
  • Carbonyl group
  • Organofluoride
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00068 g/LALOGPS
logP4.1ALOGPS
logP3.13ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.92 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity118.43 m³·mol⁻¹ChemAxon
Polarizability42.16 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bs-3984300000-6cb2fa3433de5f97b0b52017-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0120900000-71976a981e3993c625192017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-8790400000-04eca894b72f881e96b22017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fba-4940000000-cfc4e5bb9b9da44655132017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056u-0460900000-0ed3ef55dc9d02674b062017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-1890200000-f14c0bc82cf269384cc32017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-4920000000-2f8ca628ee4fb39441672017-10-06View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
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 LinkNot Available
METLIN IDNot Available
PubChem Compound9826472
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available