Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:04:47 UTC
Update Date2021-09-14 15:44:38 UTC
HMDB IDHMDB0060871
Secondary Accession Numbers
  • HMDB60871
Metabolite Identification
Common NameRPR123142
DescriptionRPR123142 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
Data?1563866116
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}-1,12-dihydroxy-9-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}-1,12-dihydroxy-9-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]1C[C@H]2OC[C@@]2(OC(C)=O)C2[C@H](OC(=O)C3=CC=CC=C3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C4=CC=CC=C4)C(C)=C([C@@H](O)C(=O)[C@]12C)C3(C)C
InChI Identifier
InChI=1S/C44H55NO14/c1-23-27(56-38(51)33(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)32(47)30(23)41(44,6)7)28(54-9)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 KeyCIHAXHLPSYZREI-JWMHMURQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentTaxanes and derivatives
Alternative Parents
Substituents
  • Taxane diterpenoid
  • Benzoate ester
  • Benzoic acid or derivatives
  • Tricarboxylic acid or derivatives
  • Benzoyl
  • Fatty acid ester
  • Monosaccharide
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty acyl
  • Tertiary alcohol
  • Carbamic acid ester
  • Carboxylic acid ester
  • Carbonic acid derivative
  • Oxetane
  • Ketone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
Water Solubility0.0064 g/LALOGPS
logP3.13ALOGPS
logP3.56ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)11.57ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area213.45 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity208.65 m³·mol⁻¹ChemAxon
Polarizability84.14 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
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-2H]-310.27830932474
DeepCCS[M+Na]+284.18730932474
AllCCS[M+H]+277.132859911
AllCCS[M+H-H2O]+277.032859911
AllCCS[M+NH4]+277.232859911
AllCCS[M+Na]+277.232859911
AllCCS[M-H]-260.232859911
AllCCS[M+Na-2H]-265.032859911
AllCCS[M+HCOO]-270.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RPR123142CO[C@H]1C[C@H]2OC[C@@]2(OC(C)=O)C2[C@H](OC(=O)C3=CC=CC=C3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C4=CC=CC=C4)C(C)=C([C@@H](O)C(=O)[C@]12C)C3(C)C4997.0Standard polar33892256
RPR123142CO[C@H]1C[C@H]2OC[C@@]2(OC(C)=O)C2[C@H](OC(=O)C3=CC=CC=C3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C4=CC=CC=C4)C(C)=C([C@@H](O)C(=O)[C@]12C)C3(C)C4470.5Standard non polar33892256
RPR123142CO[C@H]1C[C@H]2OC[C@@]2(OC(C)=O)C2[C@H](OC(=O)C3=CC=CC=C3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C4=CC=CC=C4)C(C)=C([C@@H](O)C(=O)[C@]12C)C3(C)C5077.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - RPR123142 GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - RPR123142 GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - RPR123142 GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - RPR123142 GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - RPR123142 GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 10V, Positive-QTOFsplash10-0ar1-4430021920-1fdcb6c2ae5fbce7d5802017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 20V, Positive-QTOFsplash10-0a6r-8730150900-a4add22cc060bd7357d02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 40V, Positive-QTOFsplash10-0a4i-3920220000-c93c9c3e5d9a1f6f67862017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 10V, Negative-QTOFsplash10-05fr-6320050930-2f346fbefbe907a1a7972017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 20V, Negative-QTOFsplash10-0ab9-9110180210-95f0245fd407657a1a7b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 40V, Negative-QTOFsplash10-0adi-9300060000-9988bfdb2d7ec359055b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 10V, Positive-QTOFsplash10-009x-1390480430-68eb8f6ec371075bf8832021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 20V, Positive-QTOFsplash10-0059-2590000100-ec2df03e140bbea286e42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 40V, Positive-QTOFsplash10-0a4i-3902402000-b4d92e2ad944378e099e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 10V, Negative-QTOFsplash10-05g1-6550590440-fc3e072ff0ed64e22f382021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 20V, Negative-QTOFsplash10-0a4i-8920242410-52678133ca31f558083c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - RPR123142 40V, Negative-QTOFsplash10-056u-9510001010-6b5dda9017ddd5afb4712021-10-12Wishart LabView 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 Compound131769981
PDB IDNot Available
ChEBI IDNot Available
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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. [PubMed:16902246 ]
  3. 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. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.