Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-20 22:13:20 UTC |
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Update Date | 2020-11-09 23:15:51 UTC |
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HMDB ID | HMDB0001713 |
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Secondary Accession Numbers | - HMDB0062774
- HMDB01713
- HMDB62774
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Metabolite Identification |
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Common Name | m-Coumaric acid |
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Description | m-Coumaric acid, also known as 3-coumarate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. m-Coumaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). m-Coumaric acid exists in all living organisms, ranging from bacteria to humans. m-Coumaric acid (CAS: 588-30-7) is a polyphenol metabolite from caffeic acid, formed by the gut microflora. Outside of the human body, m-Coumaric acid is found, on average, in the highest concentration within a few different foods, such as olives, corns, and beers. m-Coumaric acid has also been detected, but not quantified in, several different foods, such as carrots, strawberries, grape wines, garden tomato (var.), and bilberries. This could make m-coumaric acid a potential biomarker for the consumption of these foods. MCT-mediated absorption of phenolic compounds per se and their colonic metabolites would exert a significant impact on human health (PMID: 16870009 , 15479001 , 15479001 ). m-Coumaric acid is transported by the monocarboxylic acid transporter (MCT). The amount of this compound in human biofluids is diet-dependant. m-Coumaric acid is detected after the consumption of whole grain. |
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Structure | |
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Synonyms | Value | Source |
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(2E)-3-(3-Hydroxyphenyl)-2-propenoic acid | ChEBI | (2E)-3-(3-Hydroxyphenyl)acrylic acid | ChEBI | (e)-3-(3-Hydroxyphenyl)-2-propenoic acid | ChEBI | 3-Coumaric acid | ChEBI | m-Hydroxycinnamic acid | ChEBI | trans-3-Hydroxycinnamate | ChEBI | trans-3-Hydroxycinnamic acid | ChEBI | (2E)-3-(3-Hydroxyphenyl)prop-2-enoate | Kegg | (2E)-3-(3-Hydroxyphenyl)-2-propenoate | Generator | (2E)-3-(3-Hydroxyphenyl)acrylate | Generator | (e)-3-(3-Hydroxyphenyl)-2-propenoate | Generator | 3-Coumarate | Generator | m-Hydroxycinnamate | Generator | (2E)-3-(3-Hydroxyphenyl)prop-2-enoic acid | Generator | m-Coumarate | Generator | 3'-Hydroxycinnamate | HMDB | 3'-Hydroxycinnamic acid | HMDB | 3-(3-Hydroxyphenyl)-2-propenoate | HMDB | 3-(3-Hydroxyphenyl)-2-propenoic acid | HMDB | 3-(3-Hydroxyphenyl)acrylate | HMDB | 3-(3-Hydroxyphenyl)acrylic acid | HMDB | 3-(3-Hydroxyphenyl)acrylsaeure | HMDB | 3-(3-Hydroxyphenyl)prop-2-enoate | HMDB | 3-(3-Hydroxyphenyl)prop-2-enoic acid | HMDB | 3-Hydroxycinnamate | HMDB | 3-Hydroxycinnamic acid | HMDB | m-Hydroxy-cinnamate | HMDB | m-Hydroxy-cinnamic acid | HMDB | trans-3-Coumaric acid | HMDB | 3-Coumaric acid, (e)-isomer | HMDB | Meta-coumaric acid | HMDB | (e)-3-(3-Hydroxyphenyl)acrylic acid | HMDB | (e)-3-Hydroxycinnamic acid | HMDB | trans-3-(m-Hydroxyphenyl)-2-propenoic acid | HMDB | trans-m-Coumaric acid | HMDB | trans-m-Hydroxycinnamic acid | HMDB | m-Coumaric acid | HMDB | trans-3-Coumarate | HMDB |
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Chemical Formula | C9H8O3 |
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Average Molecular Weight | 164.158 |
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Monoisotopic Molecular Weight | 164.047344122 |
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IUPAC Name | (2E)-3-(3-hydroxyphenyl)prop-2-enoic acid |
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Traditional Name | m-coumaric acid |
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CAS Registry Number | 14755-02-3 |
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SMILES | OC(=O)\C=C\C1=CC(O)=CC=C1 |
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InChI Identifier | InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+ |
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InChI Key | KKSDGJDHHZEWEP-SNAWJCMRSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamic acids and derivatives |
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Sub Class | Hydroxycinnamic acids and derivatives |
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Direct Parent | Hydroxycinnamic acids |
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Alternative Parents | |
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Substituents | - Cinnamic acid
- Coumaric acid
- Coumaric acid or derivatives
- Hydroxycinnamic acid
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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: Biological location: Source: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 192 - 194 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0udl-1691000000-331053d0d0b85549ac0b | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udl-1691000000-331053d0d0b85549ac0b | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-1891000000-049e1d80dd47b23e8c28 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-02t9-2900000000-91ffd4c10eaed6a17632 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00y3-6390000000-f1a30e2fb9cd1fb11341 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-03xr-0900000000-4259219e89806dfe2602 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-014i-4900000000-2157a17ec65ead35585e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-00kf-9300000000-3325dd31a734dd4659bb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-03di-0900000000-be33d196fbb525019f07 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-0002-0900000000-d256885fb0f35d3d6680 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-03di-0900000000-be33d196fbb525019f07 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-0900000000-d256885fb0f35d3d6680 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-0900000000-b5ad37fb931b464df7d5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014j-1900000000-c66c146ee9509bf8a413 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fvi-9700000000-fcc332df0fcb818fe0e0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-408ac0dd815354188750 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-146bae2da386ca2d4f1a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014m-3900000000-235b38f342376d1c9f90 | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-03xr-7900000000-61ee2ad0ad164a1f7550 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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