Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-24 06:32:42 UTC |
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Update Date | 2021-09-24 06:32:42 UTC |
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HMDB ID | HMDB0304026 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 16-epivellosimine |
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Description | 16-epivellosimine is a member of the class of compounds known as macroline alkaloids. Macroline alkaloids are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. 16-epivellosimine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 16-epivellosimine can be found in a number of food items such as bitter gourd, red raspberry, orange bell pepper, and star anise, which makes 16-epivellosimine a potential biomarker for the consumption of these food products. |
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Structure | [H]C(=O)[C@]1([H])[C@@H]2CC3=C(NC4=C3C=CC=C4)[C@]3([H])C[C@H]1\C(CN23)=C/C InChI=1S/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3/b11-2-/t13-,15-,17-,18-/m0/s1 |
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Synonyms | Value | Source |
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16-Epi-vellosimine | MeSH |
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Chemical Formula | C19H20N2O |
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Average Molecular Weight | 292.3749 |
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Monoisotopic Molecular Weight | 292.157563272 |
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IUPAC Name | (1S,12S,13S,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde |
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Traditional Name | (1S,12S,13S,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde |
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CAS Registry Number | Not Available |
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SMILES | [H]C(=O)[C@]1([H])[C@@H]2CC3=C(NC4=C3C=CC=C4)[C@]3([H])C[C@H]1\C(CN23)=C/C |
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InChI Identifier | InChI=1S/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3/b11-2-/t13-,15-,17-,18-/m0/s1 |
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InChI Key | MHASSCPGKAMILD-MIOJWWSHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Macroline alkaloids |
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Sub Class | Not Available |
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Direct Parent | Macroline alkaloids |
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Alternative Parents | |
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Substituents | - Macroline skeleton
- Sarpagine-skeleton
- Vobasan skeleton
- Beta-carboline
- Pyridoindole
- 3-alkylindole
- Indole
- Indole or derivatives
- Quinuclidine
- Aralkylamine
- Benzenoid
- Piperidine
- Heteroaromatic compound
- Pyrrole
- Tertiary aliphatic amine
- Tertiary amine
- Organoheterocyclic compound
- Azacycle
- Organic nitrogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Aldehyde
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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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 IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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16-epivellosimine,1TMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([NH]C5=CC=CC=C45)[C@@H]2C[C@@H]1C3=CO[Si](C)(C)C | 2961.2 | Semi standard non polar | 33892256 | 16-epivellosimine,1TMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([NH]C5=CC=CC=C45)[C@@H]2C[C@@H]1C3=CO[Si](C)(C)C | 2739.5 | Standard non polar | 33892256 | 16-epivellosimine,1TMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([NH]C5=CC=CC=C45)[C@@H]2C[C@@H]1C3=CO[Si](C)(C)C | 3604.9 | Standard polar | 33892256 | 16-epivellosimine,1TMS,isomer #2 | C/C=C1/CN2[C@H]3C[C@@H]1[C@H](C=O)[C@@H]2CC1=C3N([Si](C)(C)C)C2=CC=CC=C12 | 2716.5 | Semi standard non polar | 33892256 | 16-epivellosimine,1TMS,isomer #2 | C/C=C1/CN2[C@H]3C[C@@H]1[C@H](C=O)[C@@H]2CC1=C3N([Si](C)(C)C)C2=CC=CC=C12 | 2705.1 | Standard non polar | 33892256 | 16-epivellosimine,1TMS,isomer #2 | C/C=C1/CN2[C@H]3C[C@@H]1[C@H](C=O)[C@@H]2CC1=C3N([Si](C)(C)C)C2=CC=CC=C12 | 3415.1 | Standard polar | 33892256 | 16-epivellosimine,2TMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([C@@H]2C[C@@H]1C3=CO[Si](C)(C)C)N([Si](C)(C)C)C1=CC=CC=C41 | 2794.2 | Semi standard non polar | 33892256 | 16-epivellosimine,2TMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([C@@H]2C[C@@H]1C3=CO[Si](C)(C)C)N([Si](C)(C)C)C1=CC=CC=C41 | 2693.3 | Standard non polar | 33892256 | 16-epivellosimine,2TMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([C@@H]2C[C@@H]1C3=CO[Si](C)(C)C)N([Si](C)(C)C)C1=CC=CC=C41 | 3362.0 | Standard polar | 33892256 | 16-epivellosimine,1TBDMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([NH]C5=CC=CC=C45)[C@@H]2C[C@@H]1C3=CO[Si](C)(C)C(C)(C)C | 3171.5 | Semi standard non polar | 33892256 | 16-epivellosimine,1TBDMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([NH]C5=CC=CC=C45)[C@@H]2C[C@@H]1C3=CO[Si](C)(C)C(C)(C)C | 2973.2 | Standard non polar | 33892256 | 16-epivellosimine,1TBDMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([NH]C5=CC=CC=C45)[C@@H]2C[C@@H]1C3=CO[Si](C)(C)C(C)(C)C | 3733.6 | Standard polar | 33892256 | 16-epivellosimine,1TBDMS,isomer #2 | C/C=C1/CN2[C@H]3C[C@@H]1[C@H](C=O)[C@@H]2CC1=C3N([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2901.4 | Semi standard non polar | 33892256 | 16-epivellosimine,1TBDMS,isomer #2 | C/C=C1/CN2[C@H]3C[C@@H]1[C@H](C=O)[C@@H]2CC1=C3N([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2970.6 | Standard non polar | 33892256 | 16-epivellosimine,1TBDMS,isomer #2 | C/C=C1/CN2[C@H]3C[C@@H]1[C@H](C=O)[C@@H]2CC1=C3N([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 3500.8 | Standard polar | 33892256 | 16-epivellosimine,2TBDMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([C@@H]2C[C@@H]1C3=CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C41 | 3141.4 | Semi standard non polar | 33892256 | 16-epivellosimine,2TBDMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([C@@H]2C[C@@H]1C3=CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C41 | 3147.4 | Standard non polar | 33892256 | 16-epivellosimine,2TBDMS,isomer #1 | C/C=C1/CN2[C@H]3CC4=C([C@@H]2C[C@@H]1C3=CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C41 | 3498.6 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 16-epivellosimine GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2022-08-08 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | Not Available | 2022-08-06 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 10V, Positive-QTOF | splash10-0006-0090000000-502966b71b3fa4b51088 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 20V, Positive-QTOF | splash10-0006-0090000000-4071f18f2e91b42c21ef | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 40V, Positive-QTOF | splash10-0059-2980000000-df284da1af082841e13d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 10V, Negative-QTOF | splash10-0006-0090000000-eb9636b759144711f704 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 20V, Negative-QTOF | splash10-01ox-0090000000-566d1bb0322a9b8a7e90 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 40V, Negative-QTOF | splash10-03di-0090000000-6466f92d5f8fff4b027f | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 10V, Positive-QTOF | splash10-0006-0090000000-30850ca9637e3e228dfd | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 20V, Positive-QTOF | splash10-0006-0090000000-d3385634a3967ef0b42c | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 40V, Positive-QTOF | splash10-072a-0190000000-27d6f13478b5896b1cf5 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 10V, Negative-QTOF | splash10-0006-0090000000-74a3146908205cd6ebec | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 20V, Negative-QTOF | splash10-03di-0090000000-972804a8372b111e10d0 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-epivellosimine 40V, Negative-QTOF | splash10-00dr-0090000000-59d95f3c81fe9761c0cc | 2021-10-21 | Wishart Lab | View Spectrum |
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