Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 19:41:51 UTC |
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Update Date | 2021-10-13 06:43:36 UTC |
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HMDB ID | HMDB0034777 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Epidermin |
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Description | Epidermin belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Epidermin has been detected, but not quantified in, a few different foods, such as barleys (Hordeum vulgare), breakfast cereal, and cereals and cereal products. This could make epidermin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Epidermin. |
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Structure | CC(C)(CC#N)OC1OC(CO)C(O)C(O)C1O InChI=1S/C11H19NO6/c1-11(2,3-4-12)18-10-9(16)8(15)7(14)6(5-13)17-10/h6-10,13-16H,3,5H2,1-2H3 |
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Synonyms | Value | Source |
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Epidermin? | HMDB | Suprofen acyl glucuronide | HMDB | Suprofen glucuronide | HMDB |
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Chemical Formula | C11H19NO6 |
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Average Molecular Weight | 261.2717 |
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Monoisotopic Molecular Weight | 261.121237345 |
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IUPAC Name | 3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile |
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Traditional Name | 3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile |
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CAS Registry Number | 126050-09-7 |
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SMILES | CC(C)(CC#N)OC1OC(CO)C(O)C(O)C1O |
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InChI Identifier | InChI=1S/C11H19NO6/c1-11(2,3-4-12)18-10-9(16)8(15)7(14)6(5-13)17-10/h6-10,13-16H,3,5H2,1-2H3 |
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InChI Key | GDSYPXWUHMRTHT-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Cyanogenic glycosides |
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Alternative Parents | |
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Substituents | - Cyanogenic glycoside
- Hexose monosaccharide
- O-glycosyl compound
- Monosaccharide
- Oxane
- Secondary alcohol
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Nitrile
- Carbonitrile
- Acetal
- Primary alcohol
- Organonitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic nitrogen compound
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | |
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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 | 718200 mg/L @ 25 °C (est) | The Good Scents Company Information System | 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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Epidermin,1TMS,isomer #1 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O | 2153.2 | Semi standard non polar | 33892256 | Epidermin,1TMS,isomer #2 | CC(C)(CC#N)OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O | 2125.3 | Semi standard non polar | 33892256 | Epidermin,1TMS,isomer #3 | CC(C)(CC#N)OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O | 2107.4 | Semi standard non polar | 33892256 | Epidermin,1TMS,isomer #4 | CC(C)(CC#N)OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C | 2124.0 | Semi standard non polar | 33892256 | Epidermin,2TMS,isomer #1 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O | 2151.3 | Semi standard non polar | 33892256 | Epidermin,2TMS,isomer #2 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O | 2151.4 | Semi standard non polar | 33892256 | Epidermin,2TMS,isomer #3 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C | 2147.2 | Semi standard non polar | 33892256 | Epidermin,2TMS,isomer #4 | CC(C)(CC#N)OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O | 2137.3 | Semi standard non polar | 33892256 | Epidermin,2TMS,isomer #5 | CC(C)(CC#N)OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C | 2138.4 | Semi standard non polar | 33892256 | Epidermin,2TMS,isomer #6 | CC(C)(CC#N)OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 2149.8 | Semi standard non polar | 33892256 | Epidermin,3TMS,isomer #1 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O | 2129.7 | Semi standard non polar | 33892256 | Epidermin,3TMS,isomer #2 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C | 2133.7 | Semi standard non polar | 33892256 | Epidermin,3TMS,isomer #3 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 2129.9 | Semi standard non polar | 33892256 | Epidermin,3TMS,isomer #4 | CC(C)(CC#N)OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 2144.3 | Semi standard non polar | 33892256 | Epidermin,4TMS,isomer #1 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 2132.7 | Semi standard non polar | 33892256 | Epidermin,1TBDMS,isomer #1 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O | 2375.8 | Semi standard non polar | 33892256 | Epidermin,1TBDMS,isomer #2 | CC(C)(CC#N)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O | 2348.1 | Semi standard non polar | 33892256 | Epidermin,1TBDMS,isomer #3 | CC(C)(CC#N)OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O | 2355.1 | Semi standard non polar | 33892256 | Epidermin,1TBDMS,isomer #4 | CC(C)(CC#N)OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C | 2358.7 | Semi standard non polar | 33892256 | Epidermin,2TBDMS,isomer #1 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O | 2570.4 | Semi standard non polar | 33892256 | Epidermin,2TBDMS,isomer #2 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O | 2576.2 | Semi standard non polar | 33892256 | Epidermin,2TBDMS,isomer #3 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C | 2570.6 | Semi standard non polar | 33892256 | Epidermin,2TBDMS,isomer #4 | CC(C)(CC#N)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O | 2576.7 | Semi standard non polar | 33892256 | Epidermin,2TBDMS,isomer #5 | CC(C)(CC#N)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C | 2580.2 | Semi standard non polar | 33892256 | Epidermin,2TBDMS,isomer #6 | CC(C)(CC#N)OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 2585.3 | Semi standard non polar | 33892256 | Epidermin,3TBDMS,isomer #1 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O | 2765.8 | Semi standard non polar | 33892256 | Epidermin,3TBDMS,isomer #2 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C | 2770.0 | Semi standard non polar | 33892256 | Epidermin,3TBDMS,isomer #3 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 2772.7 | Semi standard non polar | 33892256 | Epidermin,3TBDMS,isomer #4 | CC(C)(CC#N)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 2774.9 | Semi standard non polar | 33892256 | Epidermin,4TBDMS,isomer #1 | CC(C)(CC#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 2954.5 | Semi standard non 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 - Epidermin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fl3-8790000000-b19c70f9b7e68c966114 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Epidermin GC-MS (4 TMS) - 70eV, Positive | splash10-001r-3010490000-3b652687cfa64a5d0e51 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Epidermin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Epidermin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | 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 - Epidermin 10V, Positive-QTOF | splash10-0w30-6790000000-d83aa207a7657943c7ff | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 20V, Positive-QTOF | splash10-0f89-9510000000-9c058e2b0aef51049a46 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 40V, Positive-QTOF | splash10-001i-9200000000-55b5563a559a0b173d21 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 10V, Negative-QTOF | splash10-03dj-9380000000-4481f3cbd1cf51098f47 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 20V, Negative-QTOF | splash10-0002-9210000000-848cef8804c4fc1444ae | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 40V, Negative-QTOF | splash10-000w-9000000000-ef14016dc0add3a2283b | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 10V, Negative-QTOF | splash10-03di-0090000000-2024ad230153c118bf19 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 20V, Negative-QTOF | splash10-03di-7790000000-8287def401fc3d3524e6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 40V, Negative-QTOF | splash10-0a4i-9000000000-8a30434f521642e931db | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 10V, Positive-QTOF | splash10-03di-1290000000-937ed4ac92febbba2d73 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 20V, Positive-QTOF | splash10-000x-9000000000-2a36979e2244daa2afa3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Epidermin 40V, Positive-QTOF | splash10-001l-9000000000-3268256724ca662a3546 | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - Israil AM, Jack RW, Jung G, Sahl HG: Isolation of a new epidermin variant from two strains of Staphylococcus epidermidis--frequency of lantibiotic production in coagulase-negative staphylococci. Zentralbl Bakteriol. 1996 Jul;284(2-3):285-96. [PubMed:8837389 ]
- Schnell N, Entian KD, Schneider U, Gotz F, Zahner H, Kellner R, Jung G: Prepeptide sequence of epidermin, a ribosomally synthesized antibiotic with four sulphide-rings. Nature. 1988 May 19;333(6170):276-8. [PubMed:2835685 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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