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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:59:54 UTC
Update Date2021-09-14 15:46:11 UTC
HMDB IDHMDB0060794
Secondary Accession Numbers
  • HMDB60794
Metabolite Identification
Common Name6a-Hydrox-ypaclitaxel
Description6a-Hydrox-ypaclitaxel is a metabolite of paclitaxel. Paclitaxel is a mitotic inhibitor used in cancer chemotherapy. It was discovered in a U.S. National Cancer Institute program at the Research Triangle Institute in 1967 when Monroe E. Wall and Mansukh C. Wani isolated it from the bark of the Pacific yew tree, Taxus brevifolia and named it taxol. When it was developed commercially by Bristol-Myers Squibb (BMS) the generic name was changed to paclitaxel and the BMS compound is sold under the trademark Taxol. (Wikipedia)
Structure
Data?1563866106
SynonymsNot Available
Chemical FormulaC47H51NO15
Average Molecular Weight875.8615
Monoisotopic Molecular Weight875.345998995
IUPAC NameN-(3-{[4,12-bis(acetyloxy)-2-[(1,2,3,4,5,6-¹³C₆)benzoyloxy]-1,8,9-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-15-yl]oxy}-2-hydroxy-3-oxo-1-phenylpropyl)benzenecarboximidic acid
Traditional NameN-(3-{[4,12-bis(acetyloxy)-2-[(1,2,3,4,5,6-¹³C₆)benzoyloxy]-1,8,9-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-15-yl]oxy}-2-hydroxy-3-oxo-1-phenylpropyl)benzenecarboximidic acid
CAS Registry NumberNot Available
SMILES
CC(=O)OC1C2=C(C)C(CC(O)(C(OC(=O)[13C]3=[13CH][13CH]=[13CH][13CH]=[13CH]3)C3C4(COC4C(O)C(O)C3(C)C1=O)OC(C)=O)C2(C)C)OC(=O)C(O)C(N=C(O)C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C47H51NO15/c1-24-30(61-43(57)33(51)32(27-16-10-7-11-17-27)48-41(55)28-18-12-8-13-19-28)22-47(58)40(62-42(56)29-20-14-9-15-21-29)36-45(6,38(54)35(60-25(2)49)31(24)44(47,4)5)37(53)34(52)39-46(36,23-59-39)63-26(3)50/h7-21,30,32-37,39-40,51-53,58H,22-23H2,1-6H3,(H,48,55)/i9+1,14+1,15+1,20+1,21+1,29+1
InChI KeyNDCWHEDPSFRTDA-VEHVCKHKSA-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
  • Tetracarboxylic acid or derivatives
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • Fatty acid ester
  • Alpha-acyloxy ketone
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Cyclic alcohol
  • Tertiary alcohol
  • Carboxylic acid ester
  • Ketone
  • Oxetane
  • Secondary alcohol
  • Polyol
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Carboximidic acid
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen 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 Solubility0.01 g/LALOGPS
logP3.15ALOGPS
logP3.67ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)8.2ChemAxon
pKa (Strongest Basic)2.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area245.01 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity219.91 m³·mol⁻¹ChemAxon
Polarizability88.35 ųChemAxon
Number of Rings7ChemAxon
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]-308.2730932474
DeepCCS[M+Na]+282.07630932474
AllCCS[M+H]+283.732859911
AllCCS[M+H-H2O]+283.832859911
AllCCS[M+NH4]+283.632859911
AllCCS[M+Na]+283.632859911
AllCCS[M-H]-260.032859911
AllCCS[M+Na-2H]-264.732859911
AllCCS[M+HCOO]-269.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6a-Hydrox-ypaclitaxelCC(=O)OC1C2=C(C)C(CC(O)(C(OC(=O)[13C]3=[13CH][13CH]=[13CH][13CH]=[13CH]3)C3C4(COC4C(O)C(O)C3(C)C1=O)OC(C)=O)C2(C)C)OC(=O)C(O)C(N=C(O)C1=CC=CC=C1)C1=CC=CC=C15829.0Standard polar33892256
6a-Hydrox-ypaclitaxelCC(=O)OC1C2=C(C)C(CC(O)(C(OC(=O)[13C]3=[13CH][13CH]=[13CH][13CH]=[13CH]3)C3C4(COC4C(O)C(O)C3(C)C1=O)OC(C)=O)C2(C)C)OC(=O)C(O)C(N=C(O)C1=CC=CC=C1)C1=CC=CC=C15175.3Standard non polar33892256
6a-Hydrox-ypaclitaxelCC(=O)OC1C2=C(C)C(CC(O)(C(OC(=O)[13C]3=[13CH][13CH]=[13CH][13CH]=[13CH]3)C3C4(COC4C(O)C(O)C3(C)C1=O)OC(C)=O)C2(C)C)OC(=O)C(O)C(N=C(O)C1=CC=CC=C1)C1=CC=CC=C15957.0Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 10V, Positive-QTOFsplash10-11b9-0230031290-36d527f5fbe888bacb222017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 20V, Positive-QTOFsplash10-08fr-0890081150-8726383279feada844862017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 40V, Positive-QTOFsplash10-0a4i-2610391000-c3d7537c74792635e0052017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 10V, Negative-QTOFsplash10-1029-2130022090-6e4e98c07fba8cf923952017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 20V, Negative-QTOFsplash10-0pdl-4130093250-5760ff0eb3db7a2a5c1d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 40V, Negative-QTOFsplash10-0ab9-7521190000-ec9a84f49e6d5332d3c12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 10V, Positive-QTOFsplash10-0079-1690041030-6b4fce8956a422a6e1572021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 20V, Positive-QTOFsplash10-0cfr-1790052130-12a979088472a06db3452021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 40V, Positive-QTOFsplash10-05i3-8921110060-88d6612acbdbabe792bb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 10V, Negative-QTOFsplash10-0g34-8590074170-fb8c6ce67b49a04c17562021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 20V, Negative-QTOFsplash10-00bc-9470050010-50916cbbce78d0e79c2d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6a-Hydrox-ypaclitaxel 40V, Negative-QTOFsplash10-004i-9210200000-361aa93b5018e42fbd1d2021-10-12Wishart 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 Compound49849395
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.