Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:58 UTC |
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Update date | 2019-11-26 03:06:04 UTC |
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Primary ID | FDB012049 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Lotaustralin |
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Description | Glycoside from Trifolium repens (white clover) and other plants
Lotaustralin is a cyanogenic glucoside found in small amounts in name giving Fabaceae Lotus australis, cassava (Manihot esculenta), lima bean (Phaseolus lunatus), roseroot (Rhodiola rosea) and white clover (Trifolium repens), among other plants. Lotaustralin is structurally related to linamarin, another glucoside found in these plants, and differs from it only by the presence of an extra methyl group. Both lotaustralin and linamarin may be hydrolysed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide. |
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CAS Number | 534-67-8 |
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Structure | |
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Synonyms | Synonym | Source |
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2(R)-Hydroxy-2-methylbutyronitrile-beta-D-glucopyranoside | HMDB | 2-(beta-D-Glucopyranosyloxy)-2-methyl-(R)-butanenitrile | HMDB | 2(R)-Hydroxy-2-methylbutyronitrile-beta-D- glucopyranoside | MeSH | Lotaustralin, (S)-isomer | MeSH | Butanenitrile, 2-(beta-D-glucopyranosyloxy)-2-methyl-, (R)- | biospider | Lotaustralin | db_source |
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Predicted Properties | |
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Chemical Formula | C11H19NO6 |
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IUPAC name | 2-methyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile |
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InChI Identifier | InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3 |
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InChI Key | WEWBWVMTOYUPHH-UHFFFAOYSA-N |
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Isomeric SMILES | CCC(C)(OC1OC(CO)C(O)C(O)C1O)C#N |
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Average Molecular Weight | 261.2717 |
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Monoisotopic Molecular Weight | 261.121237345 |
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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
- 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 | |
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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 - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 50.57%; H 7.33%; N 5.36%; O 36.74% | DFC |
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Melting Point | Mp 139° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]20D -26.4 (H2O) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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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 | Lotaustralin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fef-8790000000-d454286498bdc1d9e13f | Spectrum | Predicted GC-MS | Lotaustralin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001r-4001590000-5e0039f60e7278697d85 | Spectrum | Predicted GC-MS | Lotaustralin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Lotaustralin, 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 | splash10-0w30-7980000000-3a978648b67dd80be4fb | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f89-9500000000-3e356cb2d2384f50f2ef | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9200000000-afb8c395ff62b7b82250 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03dj-9370000000-ada45f93e850699107ba | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9210000000-8466a5626668275341b0 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00sj-9000000000-0527104530bbf9ac9fd4 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-2190000000-a92ee2fbaaa09afe368f | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a59-9100000000-3039433a4bbd413b8481 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9100000000-9382edde2cf9fde3c173 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0090000000-a1ae1ea792d89a4c1974 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-5950000000-1d766a073aad7b5c983d | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05ai-9000000000-c6f23f2a0abdfb4311b8 | 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 | C08334 |
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Pubchem Compound ID | 441467 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | DBZ32-R:HCT86-F |
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EAFUS ID | Not Available |
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Dr. Duke ID | LOTAUSTRALIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001448 |
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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 | Lotaustralin |
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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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Food | Content Range | Average | Reference |
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Food | | | Reference |
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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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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