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 10:06:58 UTC |
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Update Date | 2021-09-24 10:06:58 UTC |
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HMDB ID | HMDB0304482 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | secologanin |
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Description | Secologanin is a member of the class of compounds known as terpene glycosides. Terpene glycosides are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Thus, secologanin is considered to be an isoprenoid lipid molecule. Secologanin is soluble (in water) and a very weakly acidic compound (based on its pKa). Secologanin can be found in a number of food items such as oyster mushroom, flaxseed, nectarine, and cereals and cereal products, which makes secologanin a potential biomarker for the consumption of these food products. Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively . |
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Structure | COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CC=O InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1 |
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Synonyms | Value | Source |
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3-Ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester | ChEBI | METHYL (2S,3R,4S)-2-(BETA-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylATE | ChEBI | Methyl (2S,3R,4S)-4-(formylmethyl)-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate | ChEBI | Secologanin | ChEBI | 3-Ethenyl-2-(b-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylate, methyl ester | Generator | 3-Ethenyl-2-(b-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester | Generator | 3-Ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylate, methyl ester | Generator | 3-Ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylate, methyl ester | Generator | 3-Ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester | Generator | METHYL (2S,3R,4S)-2-(b-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate | Generator | METHYL (2S,3R,4S)-2-(b-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylic acid | Generator | METHYL (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylic acid | Generator | METHYL (2S,3R,4S)-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate | Generator | METHYL (2S,3R,4S)-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylic acid | Generator | Methyl (2S,3R,4S)-4-(formylmethyl)-2-(b-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate | Generator | Methyl (2S,3R,4S)-4-(formylmethyl)-2-(b-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylic acid | Generator | Methyl (2S,3R,4S)-4-(formylmethyl)-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylic acid | Generator | Methyl (2S,3R,4S)-4-(formylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate | Generator | Methyl (2S,3R,4S)-4-(formylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylic acid | Generator |
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Chemical Formula | C17H24O10 |
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Average Molecular Weight | 388.3665 |
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Monoisotopic Molecular Weight | 388.136946988 |
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IUPAC Name | methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate |
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Traditional Name | (-)-secologanin |
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CAS Registry Number | Not Available |
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SMILES | COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CC=O |
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InChI Identifier | InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1 |
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InChI Key | CSKKDSFETGLMSB-NRZPKYKESA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. |
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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 | Terpene glycosides |
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Direct Parent | Terpene glycosides |
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Alternative Parents | |
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Substituents | - Terpene glycoside
- Glycosyl compound
- Secoiridoid-skeleton
- O-glycosyl compound
- Monocyclic monoterpenoid
- Monoterpenoid
- Sugar acid
- Monosaccharide
- Oxane
- Alpha-hydrogen aldehyde
- Vinylogous ester
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Methyl ester
- Carboxylic acid ester
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Monocarboxylic acid or derivatives
- Acetal
- Carboxylic acid derivative
- Polyol
- Primary alcohol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Aldehyde
- Organooxygen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 IndicesDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - secologanin GC-MS (Non-derivatized) | splash10-0gb9-2941000000-d1989e58bf06ee4cf380 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - secologanin GC-MS (Non-derivatized) | splash10-0gdr-2931000000-c41c7965ee5f98595452 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - secologanin GC-MS (Non-derivatized) | splash10-0gb9-2931000000-c7d5b403f8c624e91877 | 2014-06-16 | HMDB team, MONA, MassBank | 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 - secologanin 10V, Positive-QTOF | splash10-070i-0955000000-d2599f28cf7a95703756 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 20V, Positive-QTOF | splash10-06vs-1931000000-a09d52f1f1cf62ee287d | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 40V, Positive-QTOF | splash10-052r-9700000000-d0e2b29a1c685fcd4c86 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 10V, Negative-QTOF | splash10-004r-1569000000-626e940a7c2b3725a4b0 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 20V, Negative-QTOF | splash10-02di-3945000000-5047d0b9654c59e24afc | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 40V, Negative-QTOF | splash10-002f-4920000000-79158472c746f9f83e9f | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 10V, Positive-QTOF | splash10-009i-0849000000-559ffea33d0bf7fe8f95 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 20V, Positive-QTOF | splash10-001i-0910000000-daf99a97c8d320310dda | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 40V, Positive-QTOF | splash10-0mpp-8940000000-d1c75f2aaecb96f2cb03 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 10V, Negative-QTOF | splash10-0002-0911000000-2bfe9ec0a38a1fbfb058 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 20V, Negative-QTOF | splash10-03y0-3739000000-808031158bd3414bf3fd | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - secologanin 40V, Negative-QTOF | splash10-0apm-4911000000-03618a6e12c1993b6821 | 2021-10-21 | Wishart Lab | View Spectrum |
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