Cabazitaxel (CHEM022367)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:30:07 UTC
Update Date2016-11-09 01:17:28 UTC
Accession NumberCHEM022367
Identification
Common NameCabazitaxel
ClassSmall Molecule
DescriptionA tetracyclic diterpenoid that is 10-deacetylbaccatin III having O-methyl groups attached at positions 7 and 10 as well as an O-(2R,3S)-3--2-hydroxy-3-phenylpropanoyl group attached at position 13. Acts as a microtubule inhibitor, binds tubulin and promotes microtubule assembly and simultaneously inhibits disassembly.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CabazitaxelumChEBI
JevtanaKegg
Taxoid XRP6258HMDB
KabazitaxelMeSH
Chemical FormulaC45H57NO14
Average Molecular Mass835.932 g/mol
Monoisotopic Mass835.378 g/mol
CAS Registry Number183133-96-2
IUPAC Name(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate
Traditional Namecabazitaxel
SMILES[H][C@@](O)([C@@H](NC(=O)OC(C)(C)C)C1=CC=CC=C1)C(=O)O[C@@]1([H])C[C@@]2(O)[C@@]([H])(OC(=O)C3=CC=CC=C3)[C@]3([H])[C@@]4(CO[C@]4([H])C[C@]([H])(OC)[C@@]3(C)C(=O)[C@]([H])(OC)C(=C1C)C2(C)C)OC(C)=O
InChI IdentifierInChI=1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1
InChI KeyBMQGVNUXMIRLCK-OAGWZNDDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassNot Available
Direct ParentBenzazepines
Alternative Parents
Substituents
  • Benzazepine
  • Azepine
  • Imidazole-4-carbonyl group
  • Aryl-aldehyde
  • N-substituted imidazole
  • Piperidine
  • Benzenoid
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic oxide
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aldehyde
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • 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 Solubility0.0041 g/LALOGPS
logP3.69ALOGPS
logP4.2ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)11.97ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area202.45 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity213.4 m³·mol⁻¹ChemAxon
Polarizability86.39 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0560-4210021920-cfe7bca2e816c750b927Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-8720051900-f9830c3fa7f065c90a7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6900480000-305aa5a26586210ddaeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-6520060940-56520d63332c6b16b932Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-7200090210-2482a20c2ef7e8b60901Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9300050000-51a40ac30e5efd33b739Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-057j-0390350010-f59c18861840c9edd5acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06w9-2790000100-ef16e22c38ab8ef57b0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-3910001000-ed8392d91c8613a519fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-071i-6770090850-e3ffa0bcc67aa375fef1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-7750090510-a6339783dd488a76cf29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-9820000000-5b21c3d5026480e5af06Spectrum
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 IDDB06772
HMDB IDHMDB0015672
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCabazitaxel
Chemspider ID8029779
ChEBI ID63584
PubChem Compound ID9854073
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=21174534
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21339064
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21406025
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21448449
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21455038
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21461278
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21463139
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21695098
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21734586
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21748753
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21770474
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22048000
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22079047
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22111007
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22229405
16. Galsky MD, Dritselis A, Kirkpatrick P, Oh WK: Cabazitaxel. Nat Rev Drug Discov. 2010 Sep;9(9):677-8. doi: 10.1038/nrd3254.
17. Nightingale G, Ryu J: Cabazitaxel (jevtana): a novel agent for metastatic castration-resistant prostate cancer. P T. 2012 Aug;37(8):440-8.
18. Kort A, Hillebrand MJ, Cirkel GA, Voest EE, Schinkel AH, Rosing H, Schellens JH, Beijnen JH: Quantification of cabazitaxel, its metabolite docetaxel and the determination of the demethylated metabolites RPR112698 and RPR123142 as docetaxel equivalents in human plasma by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Apr 15;925:117-23. doi: 10.1016/j.jchromb.2013.02.034. Epub 2013 Mar 5.
19. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
20. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
21. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
22. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
23. The lipid handbook with CD-ROM