Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:34 UTC |
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Update date | 2020-09-17 15:33:07 UTC |
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Primary ID | FDB000432 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Moupinamide |
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Description | Moupinamide, also known as Alfrutamide or N-feruloyltyramine or N-trans-feruloyltyramine (NTF), belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is also classified as a phenylpropanoid amide. Phenylpropanoids consist of a six-carbon, aromatic phenyl group and a three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. A phenylpropanoid amide has an amide group incorporated into its propanoid chain. There are two known isomers of N-Feruloyltyramine, N-trans-Feruloyltyramine and N-cis-Feruloyltyramine. Moupinamide is a largely neutral molecule, that is somewhat insoluble in water. It exists as a pale yellow oil. Moupinamide or N-trans-Feruloyltyramine is found in black and white peppers. N-cis-Feruloyltyramine has been identified in yellow bell peppers, red bell peppers and in a lower concentration in orange bell peppers, green bell peppers, celery leaves, hyssops, quinoa, agars, and oxheart cabbages. Moupinamide is an inhibitor of COX 1 and COX 2 and has potential antioxidant properties (PMID: 19807156) |
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CAS Number | 66648-43-9 |
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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 | C18H19NO4 |
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IUPAC name | (Z,2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid |
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InChI Identifier | InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+ |
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InChI Key | NPNNKDMSXVRADT-WEVVVXLNSA-N |
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Isomeric SMILES | COC1=CC(\C=C\C(=O)NCCC2=CC=C(O)C=C2)=CC=C1O |
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Average Molecular Weight | 313.3478 |
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Monoisotopic Molecular Weight | 313.131408101 |
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Classification |
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Description | Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | Methoxyphenols |
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Direct Parent | Methoxyphenols |
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Alternative Parents | |
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Substituents | - Methoxyphenol
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Styrene
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Carboximidic acid
- Carboximidic acid derivative
- Ether
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organopnictogen compound
- Organic nitrogen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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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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 69.00%; H 6.11%; N 4.47%; O 20.42% | DFC |
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Melting Point | Mp 144.5-145° | 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 | Not Available | |
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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 | Moupinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4j-0930000000-0d34a7b54bbeaebc282b | Spectrum | Predicted GC-MS | Moupinamide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00dl-9433600000-1e204cd575b97a4b0e8e | Spectrum | Predicted GC-MS | Moupinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Moupinamide, 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 - , negative | splash10-03di-0509000000-7a8a88d076bfbf1cf48c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-00ba-1900000000-1acd727ab1a27d74943c | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01p9-0902000000-35cbd3fbcb8058d64329 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kr-0900000000-714a65fcbd5aa8249bea | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0avs-3900000000-cdd8344e1c4c188399fb | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0419000000-87271f4c26fc442256b3 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08ic-0922000000-64a362d838af2e86e0dc | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002f-3900000000-b725e376ed0d4ee8b405 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0209000000-c1a4d6d9de34cccce22b | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03k9-0913000000-efa7c33a7ab2898ad0e3 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-2920000000-c1af345555bf57620ee1 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0009000000-5cd9c8e6e0b2900b51af | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ri-0902000000-10d6192946f54c2146a7 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000x-1920000000-bbb470c57468688aaedc | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4444168 |
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ChEMBL ID | CHEMBL206555 |
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KEGG Compound ID | C02717 |
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Pubchem Compound ID | 5280537 |
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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 | HMDB29365 |
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CRC / DFC (Dictionary of Food Compounds) ID | BCB62-V:BCB61-U |
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EAFUS ID | Not Available |
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Dr. Duke ID | N-TRANS-FERULOYL-TYRAMINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00025334 |
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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 | Not Available |
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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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