Record Information |
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Version | 1.0 |
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Created at | 2006-05-22 14:17:55 UTC |
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Updated at | 2021-08-19 20:22:34 UTC |
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NP-MRD ID | NP0000110 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 3,4,5-Trimethoxycinnamic acid |
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Description | 3, 4, 5-Trimethoxycinnamic acid is a methoxycinnamic acid with three methoxy substituents at the 3-, 4- and 5-positions. It has a role as an allergen. It is a conjugate acid of a 3,4,5-trimethoxycinnamate. 3, 4, 5-Trimethoxycinnamic acid is an organic acid found in normal human urine (PMID: 6992730 , 6511847 ). Trimethoxycinnamate is a natural aromatic ester from Piper longum that inhibits expression of cell adhesion molecules on endothelial cells (TNF- -induced expression of intercellular adhesion molecule-1 (ICAM-1) and E-Selectin and vascular adhesion molecules-1 (VCAM-1)), without being toxic to endothelial cells. (PMID: 16313198 ). |
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Structure | COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+ |
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Synonyms | Value | Source |
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3,4,5-Trimethoxycinnamate | Generator | 3,4,5-Trimethoxy cinnamate | HMDB | 3,4,5-Trimethoxy cinnamic acid | HMDB | 3,4,5-Trimethoxyphenylacrylate | HMDB | 3,4,5-Trimethoxyphenylacrylic acid | HMDB | O-Methylsinapate | HMDB | O-Methylsinapic acid | HMDB | (2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoate | HMDB | 3-(3,4,5-Trimethoxyphenyl)-2-propenoic acid | HMDB | 3,4,5-Trimethoxycinnamic acid | MeSH |
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Chemical Formula | C12H14O5 |
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Average Mass | 238.2366 Da |
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Monoisotopic Mass | 238.08412 Da |
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IUPAC Name | (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid |
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Traditional Name | 3,4,5-trimethoxycinnamic acid |
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CAS Registry Number | 90-50-6 |
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SMILES | COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC |
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InChI Identifier | InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+ |
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InChI Key | YTFVRYKNXDADBI-SNAWJCMRSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, simulated) | V.dorna83 | | | 2021-08-10 | View Spectrum |
| Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. |
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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 | Coumaric acids and derivatives |
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Alternative Parents | |
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Substituents | - Cinnamic acid
- Coumaric acid or derivatives
- Phenoxy compound
- Anisole
- Methoxybenzene
- Styrene
- Phenol ether
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Ether
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Organooxygen compound
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Jenner AM, Rafter J, Halliwell B: Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free Radic Biol Med. 2005 Mar 15;38(6):763-72. [PubMed:15721987 ]
- Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [PubMed:6511847 ]
- Kissling E: [The detection of Azotobacter and its significance in criminal technical soil examinations]. Arch Kriminol. 1980;165(1-2):27-34. [PubMed:6992730 ]
- Kumar S, Arya P, Mukherjee C, Singh BK, Singh N, Parmar VS, Prasad AK, Ghosh B: Novel aromatic ester from Piper longum and its analogues inhibit expression of cell adhesion molecules on endothelial cells. Biochemistry. 2005 Dec 6;44(48):15944-52. [PubMed:16313198 ]
- Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
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