Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:06 UTC |
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Update date | 2019-11-26 03:06:32 UTC |
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Primary ID | FDB012300 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Auraptene |
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Description | Isolated from Citrus aurantium (Seville orange) and bael fruit (Aegle marmelos)
Auraptene is a natural bioactive monoterpene coumarin ether. It was first isolated from members of the genus Citrus. Auraptene has shown a remarkable effect in the prevention of degenerative diseases. Many studies have reported the effect of auraptene as a chemopreventative agent against cancers of liver, skin, tongue, esophagus, and colon in rodent models. The effect in humans is not yet known. Auraptene is found in many foods, some of which are citrus, fruits, sweet orange, and lemon. |
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CAS Number | 495-02-3 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C19H22O3 |
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IUPAC name | 7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one |
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InChI Identifier | InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+ |
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InChI Key | RSDDHGSKLOSQFK-RVDMUPIBSA-N |
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Isomeric SMILES | CC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1 |
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Average Molecular Weight | 298.3762 |
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Monoisotopic Molecular Weight | 298.15689457 |
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Classification |
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Description | Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene lactones |
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Direct Parent | Terpene lactones |
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Alternative Parents | |
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Substituents | - Terpene lactone
- Coumarin
- Aromatic monoterpenoid
- Benzopyran
- Bicyclic monoterpenoid
- Monoterpenoid
- 1-benzopyran
- Alkyl aryl ether
- Pyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Lactone
- Oxacycle
- Ether
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: 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 | Auraptene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-02u0-8890000000-e171be9caec4d2a11ee5 | Spectrum | Predicted GC-MS | Auraptene, 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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MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0040-0951000000-79a592191716b8a00de8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-03di-0900000000-29a7bac9e8f94ca0d09c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-08fr-1900000000-b149439e3218a537d0ac | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0490000000-32af6826fbefdf3a35ac | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-07br-5960000000-d750ef85cd2d4a24a646 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gb9-9500000000-d8284943e9e7d046ea7e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0390000000-50c66a59f956b01fdb9a | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0930000000-1a7ac827ff79742e805c | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-1900000000-7a051e8b339080b6467d | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03dj-1940000000-dc613a802ac097906469 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-ebcff9e2f7b33fef0429 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0159-0900000000-833c0e8e483ddb0387a6 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dj-0970000000-509fac58feb4fa761513 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03ea-9500000000-190906af7b5b2a65c2f4 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0929-9700000000-4aeadfc84ff6db8dd015 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 1267148 |
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ChEMBL ID | CHEMBL307341 |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 1550607 |
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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 | HMDB34054 |
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CRC / DFC (Dictionary of Food Compounds) ID | HFS51-H:HFS51-H |
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EAFUS ID | Not Available |
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Dr. Duke ID | AURAPTENE|AURAPTEN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00029763 |
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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 | Auraptene |
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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 | — 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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