Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-04 18:59:54 UTC |
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Update Date | 2021-09-14 15:46:11 UTC |
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HMDB ID | HMDB0060794 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 6a-Hydrox-ypaclitaxel |
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Description | 6a-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) |
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Structure | 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=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 |
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Synonyms | Not Available |
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Chemical Formula | C47H51NO15 |
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Average Molecular Weight | 875.8615 |
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Monoisotopic Molecular Weight | 875.345998995 |
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IUPAC Name | N-(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 |
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Traditional Name | N-(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 |
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CAS Registry Number | Not Available |
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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 |
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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 |
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InChI Key | NDCWHEDPSFRTDA-VEHVCKHKSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Diterpenoids |
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Direct Parent | Taxanes and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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