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Record Information
Version3.6
Creation Date2013-07-04 18:59:54 UTC
Update Date2016-02-11 08:13:01 UTC
HMDB IDHMDB60794
Secondary Accession NumbersNone
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
Thumb
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=1/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 KeyInChIKey=NDCWHEDPSFRTDA-VEHVCKHKNA-N
Chemical Taxonomy
ClassificationNot classified
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 Solubility0.01 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity219.91 m3·mol-1ChemAxon
Polarizability88.35 Å3ChemAxon
Number of Rings7ChemAxon
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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00773
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 LinkHMDB60794
Metagene LinkHMDB60794
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available