| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:11:15 UTC |
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| Update date | 2019-11-26 03:10:00 UTC |
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| Primary ID | FDB014417 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | (-)-Matairesinol |
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| Description | (-)-Matairesinol belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring (-)-Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa) (-)-Matairesinol is found, on average, in the highest concentration within a few different foods, such as sesames, burdocks, and flaxseeds and in a lower concentration in radish (var.), grape wines, and miso (-)-Matairesinol has also been detected, but not quantified in, several different foods, such as cardamoms, canada blueberries, beans, arctic blackberries, and kelps. This could make (-)-matairesinol a potential biomarker for the consumption of these foods. |
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| CAS Number | 580-72-3 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C20H34O6 |
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| IUPAC name | 3,4-bis[(4-hydroxy-3-methoxycyclohexyl)methyl]oxolan-2-one |
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| InChI Identifier | InChI=1S/C20H34O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h12-19,21-22H,3-11H2,1-2H3 |
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| InChI Key | ARQURIMKGVUGBH-UHFFFAOYSA-N |
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| Isomeric SMILES | COC1CC(CC2COC(=O)C2CC2CCC(O)C(C2)OC)CCC1O |
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| Average Molecular Weight | 370.486 |
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| Monoisotopic Molecular Weight | 370.235538815 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. |
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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 | Alcohols and polyols |
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| Direct Parent | Cyclohexanols |
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| Alternative Parents | |
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| Substituents | - Cyclohexanol
- Gamma butyrolactone
- Cyclic alcohol
- Tetrahydrofuran
- Lactone
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- 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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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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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 67.03%; H 6.19%; O 26.79% | DFC |
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| Melting Point | Mp 119° (anhyd.) | 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 -40 (c, 0.1 in EtOH) | DFC |
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| Spectroscopic UV Data | 280 () (EtOH) (Berdy) | DFC |
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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 | Not Available |
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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 | splash10-00di-0119000000-ae72af1af4f3cfa6528c | 2015-05-27 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0uxu-0596000000-99bed884feb6e3715ddc | 2015-05-27 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fr7-6960000000-5b62d3b5ac51ccd551fd | 2015-05-27 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0009000000-8304813b564f8cb08e8a | 2015-05-27 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fvi-0119000000-229bd20dbf53c370dde9 | 2015-05-27 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0aba-1936000000-bf6ea59c6a4c08f732d4 | 2015-05-27 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 106491 |
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| ChEMBL ID | CHEMBL425148 |
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| KEGG Compound ID | C10682 |
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| Pubchem Compound ID | 119205 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | 595 |
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| DrugBank ID | DB04200 |
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| HMDB ID | HMDB35698 |
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| CRC / DFC (Dictionary of Food Compounds) ID | JRV93-M:JQK13-E |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | MATAIRESINOL|MATIRESINOL |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00000606 |
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| HET ID | MAX |
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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 | Matairesinol |
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| Phenol-Explorer Metabolite ID | 595 |
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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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| anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | cAMP-phosphodiesterase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | | insecticide | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | | anti angiogenic | 48422 | An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. | CHEBI |
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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 |
- Muller U, Mrestani Y, Neubert R, Drager B: Chiral separation of the plant lignan matairesinol by capillary electrophoresis. Electrophoresis. 2008 Sep;29(17):3582-7. Pubmed [Structure]
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| Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— 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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