Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-12 01:30:40 UTC |
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Update Date | 2022-03-07 02:56:24 UTC |
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HMDB ID | HMDB0039961 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside |
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Description | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside, also known as passiedulin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside has been detected, but not quantified in, fruits. This could make (S)-2-hydroxy-2-phenylacetonitrile O-b-D-allopyranoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside. |
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Structure | OCC1OC(OC(C#N)C2=CC=CC=C2)C(O)C(O)C1O InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2 |
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Synonyms | Value | Source |
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Passiedulin | HMDB |
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Chemical Formula | C14H17NO6 |
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Average Molecular Weight | 295.2879 |
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Monoisotopic Molecular Weight | 295.105587281 |
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IUPAC Name | 2-phenyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile |
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Traditional Name | 2-phenyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile |
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CAS Registry Number | Not Available |
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SMILES | OCC1OC(OC(C#N)C2=CC=CC=C2)C(O)C(O)C1O |
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InChI Identifier | InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2 |
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InChI Key | ZKSZEJFBGODIJW-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
- Monocyclic benzene moiety
- Monosaccharide
- Oxane
- Benzenoid
- Secondary alcohol
- Polyol
- Nitrile
- Carbonitrile
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Primary alcohol
- Organonitrogen compound
- Hydrocarbon derivative
- Alcohol
- Organopnictogen compound
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic 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 | 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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(S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,1TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O)C(O)C1O | 2510.4 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,1TMS,isomer #2 | C[Si](C)(C)OC1C(OC(C#N)C2=CC=CC=C2)OC(CO)C(O)C1O | 2466.5 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,1TMS,isomer #3 | C[Si](C)(C)OC1C(O)C(CO)OC(OC(C#N)C2=CC=CC=C2)C1O | 2456.2 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,1TMS,isomer #4 | C[Si](C)(C)OC1C(CO)OC(OC(C#N)C2=CC=CC=C2)C(O)C1O | 2462.1 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C)C(O)C1O | 2458.1 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TMS,isomer #2 | C[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O)C(O[Si](C)(C)C)C1O | 2436.8 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TMS,isomer #3 | C[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O)C(O)C1O[Si](C)(C)C | 2460.7 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TMS,isomer #4 | C[Si](C)(C)OC1C(CO)OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C)C1O | 2447.0 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TMS,isomer #5 | C[Si](C)(C)OC1C(OC(C#N)C2=CC=CC=C2)OC(CO)C(O)C1O[Si](C)(C)C | 2438.4 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TMS,isomer #6 | C[Si](C)(C)OC1C(CO)OC(OC(C#N)C2=CC=CC=C2)C(O)C1O[Si](C)(C)C | 2439.7 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,3TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O | 2409.0 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,3TMS,isomer #2 | C[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C | 2430.6 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,3TMS,isomer #3 | C[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 2426.2 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,3TMS,isomer #4 | C[Si](C)(C)OC1C(CO)OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 2428.2 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,4TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 2394.4 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O)C(O)C1O | 2715.3 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1C(OC(C#N)C2=CC=CC=C2)OC(CO)C(O)C1O | 2721.0 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1C(O)C(CO)OC(OC(C#N)C2=CC=CC=C2)C1O | 2720.6 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC(C#N)C2=CC=CC=C2)C(O)C1O | 2716.6 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)C(O)C1O | 2885.3 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O)C(O[Si](C)(C)C(C)(C)C)C1O | 2889.5 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O)C(O)C1O[Si](C)(C)C(C)(C)C | 2892.2 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)C1O | 2897.1 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC1C(OC(C#N)C2=CC=CC=C2)OC(CO)C(O)C1O[Si](C)(C)C(C)(C)C | 2897.2 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC(C#N)C2=CC=CC=C2)C(O)C1O[Si](C)(C)C(C)(C)C | 2903.1 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O | 3058.9 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C | 3059.3 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 3057.6 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC(C#N)C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 3034.5 | Semi standard non polar | 33892256 | (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC(C#N)C2=CC=CC=C2)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 | 3216.7 | 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 - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside GC-MS (Non-derivatized) - 70eV, Positive | splash10-02e9-5970000000-af7eea9783215b5077ec | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside GC-MS (4 TMS) - 70eV, Positive | splash10-014i-2411490000-eb6d4c8c77d360144d24 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 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 - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 10V, Positive-QTOF | splash10-001j-0950000000-94af28ff3325aa91829f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 20V, Positive-QTOF | splash10-00lr-0900000000-c209318aed53a776a604 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 40V, Positive-QTOF | splash10-067i-3900000000-f46229fde33733da738a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 10V, Negative-QTOF | splash10-000x-1890000000-a1a34454361f8a461a19 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 20V, Negative-QTOF | splash10-001i-2910000000-9efa8331da9f7f35adb0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 40V, Negative-QTOF | splash10-003r-9800000000-6551bbcd67cdb9809506 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 10V, Negative-QTOF | splash10-0006-0950000000-911e901878111f3552da | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 20V, Negative-QTOF | splash10-0gc0-1910000000-e65f091dbdc8f43dd35c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 40V, Negative-QTOF | splash10-00lr-2900000000-ae791f613076bd282606 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 10V, Positive-QTOF | splash10-014j-0930000000-b073c628b5ae90962ddb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 20V, Positive-QTOF | splash10-0159-1930000000-0195cac2f79233b86e61 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-2-Hydroxy-2-phenylacetonitrile O-b-D-allopyranoside 40V, Positive-QTOF | splash10-014i-6900000000-14cef03a9110265ac2a2 | 2021-09-24 | 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) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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