Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-09 16:15:29 UTC |
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Update Date | 2021-09-14 15:19:30 UTC |
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HMDB ID | HMDB0061054 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Desacetylvinblastine |
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Description | Desacetylvinblastine is a metabolite of vinblastine. Vinblastine is an antimicrotubule drug used to treat certain kinds of cancer, including Hodgkin's lymphoma, non-small cell lung cancer, breast cancer, head and neck cancer, and testicular cancer. It is also used to treat Langerhans cell histiocytosis. Vinblastine was traditionally obtained from Catharanthus roseus, also known as Vinca rosea, a Madagascar Periwinkle. It is generated in the plant by the joining of two alkaloids catharanthine and vindoline. (Wikipedia) |
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Structure | [H][C@]12CN(C[C@](O)(CC)C1)CCC1=C(NC3=CC=CC=C13)[C@@](C2)(C(=O)OC)C1=C(OC)C=C2N(C)[C@@H]3C4(CCN5CC=C[C@](CC)([C@@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2=C1 InChI=1S/C44H56N4O8/c1-7-40(52)22-26-23-43(38(50)55-5,34-28(14-18-47(24-26)25-40)27-12-9-10-13-31(27)45-34)30-20-29-32(21-33(30)54-4)46(3)36-42(29)16-19-48-17-11-15-41(8-2,35(42)48)37(49)44(36,53)39(51)56-6/h9-13,15,20-21,26,35-37,45,49,52-53H,7-8,14,16-19,22-25H2,1-6H3/t26-,35-,36+,37+,40-,41+,42?,43-,44-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C44H56N4O8 |
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Average Molecular Weight | 768.9374 |
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Monoisotopic Molecular Weight | 768.409814788 |
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IUPAC Name | methyl (9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraen-13-yl]-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate |
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Traditional Name | methyl (9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraen-13-yl]-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate |
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CAS Registry Number | Not Available |
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SMILES | [H][C@]12CN(C[C@](O)(CC)C1)CCC1=C(NC3=CC=CC=C13)[C@@](C2)(C(=O)OC)C1=C(OC)C=C2N(C)[C@@H]3C4(CCN5CC=C[C@](CC)([C@@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2=C1 |
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InChI Identifier | InChI=1S/C44H56N4O8/c1-7-40(52)22-26-23-43(38(50)55-5,34-28(14-18-47(24-26)25-40)27-12-9-10-13-31(27)45-34)30-20-29-32(21-33(30)54-4)46(3)36-42(29)16-19-48-17-11-15-41(8-2,35(42)48)37(49)44(36,53)39(51)56-6/h9-13,15,20-21,26,35-37,45,49,52-53H,7-8,14,16-19,22-25H2,1-6H3/t26-,35-,36+,37+,40-,41+,42?,43-,44-/m0/s1 |
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InChI Key | NDMPLJNOPCLANR-CYJJREDESA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aryl 1,2,4-triazolones. These are aromatic heterocyclic compounds containing a 1,2,4-triazolone moiety that is substituted at the 5-position with an aryl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Azoles |
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Sub Class | Triazoles |
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Direct Parent | Aryl 1,2,4-triazolones |
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Alternative Parents | |
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Substituents | - Aryl 1,2,4-triazol-3-one
- Triazolopyridine
- Pyridinone
- Pyridine
- Heteroaromatic compound
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Organic oxygen compound
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Desacetylvinblastine,1TMS,isomer #1 | CC[C@]1(O[Si](C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 5617.2 | Semi standard non polar | 33892256 | Desacetylvinblastine,1TMS,isomer #1 | CC[C@]1(O[Si](C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 5562.2 | Standard non polar | 33892256 | Desacetylvinblastine,1TMS,isomer #1 | CC[C@]1(O[Si](C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 7787.8 | Standard polar | 33892256 | Desacetylvinblastine,1TMS,isomer #2 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C)[C@]3(O)C(=O)OC)C2)C1 | 5626.9 | Semi standard non polar | 33892256 | Desacetylvinblastine,1TMS,isomer #2 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C)[C@]3(O)C(=O)OC)C2)C1 | 5517.7 | Standard non polar | 33892256 | Desacetylvinblastine,1TMS,isomer #2 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C)[C@]3(O)C(=O)OC)C2)C1 | 7597.5 | Standard polar | 33892256 | Desacetylvinblastine,1TMS,isomer #3 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C)C(=O)OC)C2)C1 | 5632.9 | Semi standard non polar | 33892256 | Desacetylvinblastine,1TMS,isomer #3 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C)C(=O)OC)C2)C1 | 5554.6 | Standard non polar | 33892256 | Desacetylvinblastine,1TMS,isomer #3 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C)C(=O)OC)C2)C1 | 7718.7 | Standard polar | 33892256 | Desacetylvinblastine,1TMS,isomer #4 | CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 5669.1 | Semi standard non polar | 33892256 | Desacetylvinblastine,1TMS,isomer #4 | CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 5499.2 | Standard non polar | 33892256 | Desacetylvinblastine,1TMS,isomer #4 | CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 7661.7 | Standard polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #1 | CC[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 5807.5 | Semi standard non polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #1 | CC[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 5780.4 | Standard non polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #1 | CC[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 7819.7 | Standard polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #2 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C(C)(C)C)[C@]3(O)C(=O)OC)C2)C1 | 5800.7 | Semi standard non polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #2 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C(C)(C)C)[C@]3(O)C(=O)OC)C2)C1 | 5741.7 | Standard non polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #2 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C(C)(C)C)[C@]3(O)C(=O)OC)C2)C1 | 7659.6 | Standard polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #3 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C(C)(C)C)C(=O)OC)C2)C1 | 5825.0 | Semi standard non polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #3 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C(C)(C)C)C(=O)OC)C2)C1 | 5785.4 | Standard non polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #3 | CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C(C)(C)C)C(=O)OC)C2)C1 | 7769.5 | Standard polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #4 | CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C(C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 5791.9 | Semi standard non polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #4 | CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C(C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 5712.7 | Standard non polar | 33892256 | Desacetylvinblastine,1TBDMS,isomer #4 | CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C(C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C1 | 7700.8 | Standard polar | 33892256 |
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