Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:46 UTC |
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Update date | 2019-11-26 03:08:33 UTC |
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Primary ID | FDB013526 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Prunasin |
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Description | Prunasin, also known as (R)-prunasin or prulaurasin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Prunasin exists in all living organisms, ranging from bacteria to humans. Prunasin has been detected, but not quantified in, several different foods, such as peaches (Prunus persica), sour cherries (Prunus cerasus), almonds (Prunus dulcis), herbs and spices, and passion fruits (Passiflora edulis). This could make prunasin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Prunasin. |
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CAS Number | 99-18-3 |
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Structure | |
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Synonyms | Synonym | Source |
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(R)-(beta-D-Glucopyranosyloxy)phenylacetonitrile | ChEBI | (R)-alpha-(beta-D-Glucopyranosyloxy)benzene-acetonitrile | ChEBI | (R)-Mandelonitrile beta-D-glucopyranoside | ChEBI | (R)-Mandelonitrile beta-D-glucoside | ChEBI | D-Prunasin | ChEBI | (R)-Prunasin | Kegg | (R)-(b-D-Glucopyranosyloxy)phenylacetonitrile | Generator | (R)-(Β-D-glucopyranosyloxy)phenylacetonitrile | Generator | (R)-a-(b-D-Glucopyranosyloxy)benzene-acetonitrile | Generator | (R)-Α-(β-D-glucopyranosyloxy)benzene-acetonitrile | Generator | (R)-Mandelonitrile b-D-glucopyranoside | Generator | (R)-Mandelonitrile β-D-glucopyranoside | Generator | (R)-Mandelonitrile b-D-glucoside | Generator | (R)-Mandelonitrile β-D-glucoside | Generator | Mandelonitrile-beta-glucoside | MeSH | Prulaurasin | MeSH | Prunasin, (R)-isomer | MeSH | Prunasine | MeSH | (-)-(2R)-Prunasin | HMDB | (-)-Prunasin | HMDB | (2R)-(beta-D-Glucopyranosyloxy)(phenyl)acetonitrile | HMDB | (2R)-Prunasin | HMDB | Prunasin | ChEBI | (R)-(β-D-glucopyranosyloxy)phenylacetonitrile | Generator | (R)-α-(β-D-glucopyranosyloxy)benzene-acetonitrile | Generator |
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Predicted Properties | |
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Chemical Formula | C14H17NO6 |
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IUPAC name | (2R)-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+/m0/s1 |
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InChI Key | ZKSZEJFBGODIJW-GMDXDWKASA-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 - 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 56.95%; H 5.80%; N 4.74%; O 32.51% | DFC |
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Melting Point | Mp 147-148° | 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]D -29.6 (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 | Prunasin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-02e9-5970000000-af7eea9783215b5077ec | Spectrum | Predicted GC-MS | Prunasin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014i-2411490000-eb6d4c8c77d360144d24 | Spectrum | Predicted GC-MS | Prunasin, 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, Positive | splash10-014j-0930000000-b073c628b5ae90962ddb | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0159-1930000000-0195cac2f79233b86e61 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-6900000000-14cef03a9110265ac2a2 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0950000000-911e901878111f3552da | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0gc0-1910000000-e65f091dbdc8f43dd35c | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00lr-2900000000-ae791f613076bd282606 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 106360 |
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ChEMBL ID | CHEMBL1778417 |
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KEGG Compound ID | C00844 |
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Pubchem Compound ID | 119033 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17396 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB34934 |
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CRC / DFC (Dictionary of Food Compounds) ID | JDX91-A:JDX99-I |
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EAFUS ID | Not Available |
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Dr. Duke ID | PRUNASIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001454 |
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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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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 | Descriptor | ID | Definition | Reference |
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aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE | cyanogenic | | | DUKE |
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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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