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Record Information
Version3.6
Creation Date2013-07-04 19:04:41 UTC
Update Date2017-08-18 12:51:58 UTC
HMDB IDHMDB0060870
Secondary Accession Numbers
  • HMDB60870
Metabolite Identification
Common NameRPR112698
DescriptionRPR112698 is a metabolite of cabazitaxel. Cabazitaxel (previously XRP-6258, trade name Jevtana) is a semi-synthetic derivative of a natural taxoid. It was developed by Sanofi-Aventis and was approved by the U.S. Food and Drug Administration (FDA) for the treatment of hormone-refractory prostate cancer on June 17, 2010. It is a microtubule inhibitor. Cabazitaxel in combination with prednisone is a treatment option for hormone-refractory prostate cancer following or during docetaxel-based treatment. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC44H55NO14
Average Molecular Weight821.9058
Monoisotopic Molecular Weight821.362255473
IUPAC Name(1S,2S,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9-dihydroxy-12-methoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate
Traditional Name(1S,2S,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy}-1,9-dihydroxy-12-methoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate
CAS Registry NumberNot Available
SMILES
CO[C@@H]1C2=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)C3=CC=CC=C3)C3[C@@]4(CO[C@@H]4C[C@H](O)[C@@]3(C)C1=O)OC(C)=O)C2(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C1=CC=CC=C1
InChI Identifier
InChI=1S/C44H55NO14/c1-23-27(56-38(51)32(48)31(25-16-12-10-13-17-25)45-39(52)59-40(3,4)5)21-44(53)36(57-37(50)26-18-14-11-15-19-26)34-42(8,35(49)33(54-9)30(23)41(44,6)7)28(47)20-29-43(34,22-55-29)58-24(2)46/h10-19,27-29,31-34,36,47-48,53H,20-22H2,1-9H3,(H,45,52)/t27-,28-,29+,31-,32+,33+,34?,36-,42+,43-,44+/m0/s1
InChI KeyKWXAADKMZIJIMH-JWMHMURQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] propellane ring system.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentTaxanes and derivatives
Alternative Parents
Substituents
  • Taxane diterpenoid
  • Benzoate ester
  • Benzoic acid or derivatives
  • Tricarboxylic acid or derivatives
  • Benzoyl
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Monosaccharide
  • Benzenoid
  • Cyclic alcohol
  • Carbamic acid ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Ketone
  • Carbonic acid derivative
  • Oxetane
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0071 mg/mLALOGPS
logP3.14ALOGPS
logP3.56ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)11.96ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area213.45 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity208.65 m3·mol-1ChemAxon
Polarizability84.04 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00998
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0060870
      METLIN IDNot Available
      PubChem Compound10417998
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available