Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:48 UTC |
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Update date | 2019-11-26 03:08:39 UTC |
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Primary ID | FDB013582 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Sambunigrin |
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Description | Sambunigrin, also known as (2S)-sambunigrin or L-prunasin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Sambunigrin is found, on average, in the highest concentration within black elderberries (Sambucus nigra). Sambunigrin has also been detected, but not quantified in, fruits and passion fruits (Passiflora edulis). This could make sambunigrin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Sambunigrin. |
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CAS Number | 99-19-4 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C14H17NO6 |
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IUPAC name | (2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile |
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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/t9-,10-,11-,12+,13-,14-/m1/s1 |
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InChI Key | ZKSZEJFBGODIJW-YOVYLDAJSA-N |
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Isomeric SMILES | OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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Average Molecular Weight | 295.2879 |
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Monoisotopic Molecular Weight | 295.105587281 |
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Classification |
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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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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Sambunigrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-02e9-5970000000-af7eea9783215b5077ec | Spectrum | Predicted GC-MS | Sambunigrin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014i-2411490000-eb6d4c8c77d360144d24 | Spectrum | Predicted GC-MS | Sambunigrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001j-0950000000-94af28ff3325aa91829f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00lr-0900000000-c209318aed53a776a604 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-067i-3900000000-f46229fde33733da738a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000x-1890000000-a1a34454361f8a461a19 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-2910000000-9efa8331da9f7f35adb0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-003r-9800000000-6551bbcd67cdb9809506 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0950000000-911e901878111f3552da | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0gc0-1910000000-e65f091dbdc8f43dd35c | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00lr-2900000000-ae791f613076bd282606 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-0930000000-b073c628b5ae90962ddb | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0159-1930000000-0195cac2f79233b86e61 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-6900000000-14cef03a9110265ac2a2 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C04273 |
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Pubchem Compound ID | 91434 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 27761 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB34981 |
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CRC / DFC (Dictionary of Food Compounds) ID | JDX91-A:JFL71-A |
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EAFUS ID | Not Available |
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Dr. Duke ID | SAMBUNIGRIN|S-SAMBUNIGRIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00034206 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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