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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 04:02:08 UTC
Update Date2021-09-26 23:00:28 UTC
HMDB IDHMDB0249524
Secondary Accession NumbersNone
Metabolite Identification
Common NameCabozantinib
DescriptionCabozantinib, also known as BMS 907351 or XL 184, 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. Based on a literature review a significant number of articles have been published on Cabozantinib. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cabozantinib is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cabozantinib 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
BMS 907351ChEBI
BMS-907351ChEBI
XL 184ChEBI
XL-184ChEBI
XL184ChEBI
CabometyxKegg
CometriqKegg
XL184 CPDMeSH
CabozantinibMeSH
Chemical FormulaC28H24FN3O5
Average Molecular Weight501.514
Monoisotopic Molecular Weight501.169999048
IUPAC NameN'1-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}-N1-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
Traditional Namecabozantinib
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C=C1OC)C(OC1=CC=C(NC(=O)C3(CC3)C(=O)NC3=CC=C(F)C=C3)C=C1)=CC=N2
InChI Identifier
InChI=1S/C28H24FN3O5/c1-35-24-15-21-22(16-25(24)36-2)30-14-11-23(21)37-20-9-7-19(8-10-20)32-27(34)28(12-13-28)26(33)31-18-5-3-17(29)4-6-18/h3-11,14-16H,12-13H2,1-2H3,(H,31,33)(H,32,34)
InChI KeyONIQOQHATWINJY-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
  • Quinoline
  • Anilide
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • N-arylamide
  • Alkyl aryl ether
  • Halobenzene
  • Fluorobenzene
  • Aryl fluoride
  • Aryl halide
  • Cyclopropanecarboxylic acid or derivatives
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP4.01ALOGPS
logP4.66ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.46ChemAxon
pKa (Strongest Basic)5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.78 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity136.12 m³·mol⁻¹ChemAxon
Polarizability51.49 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
DeepCCS[M+H]+210.46830932474
DeepCCS[M-H]-208.07330932474
DeepCCS[M-2H]-240.95630932474
DeepCCS[M+Na]+216.38130932474
AllCCS[M+H]+220.632859911
AllCCS[M+H-H2O]+218.732859911
AllCCS[M+NH4]+222.232859911
AllCCS[M+Na]+222.732859911
AllCCS[M-H]-210.532859911
AllCCS[M+Na-2H]-210.932859911
AllCCS[M+HCOO]-211.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CabozantinibCOC1=CC2=C(C=C1OC)C(OC1=CC=C(NC(=O)C3(CC3)C(=O)NC3=CC=C(F)C=C3)C=C1)=CC=N25831.2Standard polar33892256
CabozantinibCOC1=CC2=C(C=C1OC)C(OC1=CC=C(NC(=O)C3(CC3)C(=O)NC3=CC=C(F)C=C3)C=C1)=CC=N24069.1Standard non polar33892256
CabozantinibCOC1=CC2=C(C=C1OC)C(OC1=CC=C(NC(=O)C3(CC3)C(=O)NC3=CC=C(F)C=C3)C=C1)=CC=N24560.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cabozantinib,1TMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)NC5=CC=C(F)C=C5)CC4)[Si](C)(C)C)C=C3)=C2C=C1OC4210.0Semi standard non polar33892256
Cabozantinib,1TMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)NC5=CC=C(F)C=C5)CC4)[Si](C)(C)C)C=C3)=C2C=C1OC3949.5Standard non polar33892256
Cabozantinib,1TMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)NC5=CC=C(F)C=C5)CC4)[Si](C)(C)C)C=C3)=C2C=C1OC5609.8Standard polar33892256
Cabozantinib,1TMS,isomer #2COC1=CC2=NC=CC(OC3=CC=C(NC(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C)CC4)C=C3)=C2C=C1OC4197.2Semi standard non polar33892256
Cabozantinib,1TMS,isomer #2COC1=CC2=NC=CC(OC3=CC=C(NC(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C)CC4)C=C3)=C2C=C1OC3932.4Standard non polar33892256
Cabozantinib,1TMS,isomer #2COC1=CC2=NC=CC(OC3=CC=C(NC(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C)CC4)C=C3)=C2C=C1OC5647.2Standard polar33892256
Cabozantinib,2TMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C)CC4)[Si](C)(C)C)C=C3)=C2C=C1OC4023.3Semi standard non polar33892256
Cabozantinib,2TMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C)CC4)[Si](C)(C)C)C=C3)=C2C=C1OC3649.7Standard non polar33892256
Cabozantinib,2TMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C)CC4)[Si](C)(C)C)C=C3)=C2C=C1OC5093.9Standard polar33892256
Cabozantinib,1TBDMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)NC5=CC=C(F)C=C5)CC4)[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1OC4450.5Semi standard non polar33892256
Cabozantinib,1TBDMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)NC5=CC=C(F)C=C5)CC4)[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1OC4123.0Standard non polar33892256
Cabozantinib,1TBDMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)NC5=CC=C(F)C=C5)CC4)[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1OC5561.8Standard polar33892256
Cabozantinib,1TBDMS,isomer #2COC1=CC2=NC=CC(OC3=CC=C(NC(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C(C)(C)C)CC4)C=C3)=C2C=C1OC4441.5Semi standard non polar33892256
Cabozantinib,1TBDMS,isomer #2COC1=CC2=NC=CC(OC3=CC=C(NC(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C(C)(C)C)CC4)C=C3)=C2C=C1OC4096.1Standard non polar33892256
Cabozantinib,1TBDMS,isomer #2COC1=CC2=NC=CC(OC3=CC=C(NC(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C(C)(C)C)CC4)C=C3)=C2C=C1OC5595.1Standard polar33892256
Cabozantinib,2TBDMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C(C)(C)C)CC4)[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1OC4466.1Semi standard non polar33892256
Cabozantinib,2TBDMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C(C)(C)C)CC4)[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1OC4013.2Standard non polar33892256
Cabozantinib,2TBDMS,isomer #1COC1=CC2=NC=CC(OC3=CC=C(N(C(=O)C4(C(=O)N(C5=CC=C(F)C=C5)[Si](C)(C)C(C)(C)C)CC4)[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1OC5104.5Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cabozantinib , positive-QTOFsplash10-0udi-0139180000-20096332e7e989d723922017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 10V, Positive-QTOFsplash10-0udi-0043190000-2ad3469c3893b52f7b602017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 20V, Positive-QTOFsplash10-0a4l-1297110000-e86777235501397100912017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 40V, Positive-QTOFsplash10-014i-9201000000-6b8e6247232b7eada9d02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 10V, Negative-QTOFsplash10-0udi-0413190000-a7785d888ed69543a1452017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 20V, Negative-QTOFsplash10-01tj-6819100000-068fb3a8dd9252ac2d082017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 40V, Negative-QTOFsplash10-06rm-7927000000-6d2b6684eb0a04dce7b22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 10V, Positive-QTOFsplash10-0udi-0001090000-732b2f126b6a5737b8402021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 20V, Positive-QTOFsplash10-016r-3907010000-3948adea7d9c2acde5ed2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 40V, Positive-QTOFsplash10-00kg-9216110000-54272d197a5b4624dec62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 10V, Negative-QTOFsplash10-0udi-0101090000-371cf0abc0d3798486152021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 20V, Negative-QTOFsplash10-0imj-0905320000-8a1e7cec7512e16579f22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cabozantinib 40V, Negative-QTOFsplash10-01ta-0912200000-f8177c85dcf63e875fbb2021-10-12Wishart 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 IDDB08875
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID25948202
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCabozantinib
METLIN IDNot Available
PubChem Compound25102847
PDB IDNot Available
ChEBI ID72317
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 ]