Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-02-26 10:58:06 UTC |
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Update Date | 2020-02-26 21:35:44 UTC |
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HMDB ID | HMDB0011721 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Trans-2, 3, 4-Trimethoxycinnamate |
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Description | 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\C(O)=O)C(OC)=C1OC InChI=1S/C12H14O5/c1-15-9-6-4-8(5-7-10(13)14)11(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b7-5+ |
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Synonyms | Value | Source |
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trans-2, 3, 4-Trimethoxycinnamic acid | Generator | (2E)-3-(2,3,4-Trimethoxyphenyl)-2-propenoate | HMDB | (2E)-3-(2,3,4-Trimethoxyphenyl)-2-propenoic acid | HMDB | 3-(2,3,4-Trimethoxyphenyl)-2-propenoate | HMDB | 3-(2,3,4-Trimethoxyphenyl)-2-propenoic acid | HMDB | 3-(2,3,4-Trimethoxyphenyl)acrylic acid | MeSH, HMDB | (Z)-3-(2,3,4-Trimethoxyphenyl)acrylic acid | MeSH, HMDB | (2E)-3-(2,3,4-Trimethoxyphenyl)prop-2-enoate | Generator, HMDB | trans-2,3,4-Trimethoxycinnamic acid | Generator, HMDB |
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Chemical Formula | C12H14O5 |
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Average Molecular Weight | 238.2366 |
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Monoisotopic Molecular Weight | 238.084123558 |
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IUPAC Name | (2E)-3-(2,3,4-trimethoxyphenyl)prop-2-enoic acid |
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Traditional Name | (2E)-3-(2,3,4-trimethoxyphenyl)prop-2-enoic acid |
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CAS Registry Number | 33130-03-9 |
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SMILES | COC1=CC=C(\C=C\C(O)=O)C(OC)=C1OC |
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InChI Identifier | InChI=1S/C12H14O5/c1-15-9-6-4-8(5-7-10(13)14)11(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b7-5+ |
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InChI Key | ZYOPDNLIHHFGEC-FNORWQNLSA-N |
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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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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate GC-MS (Non-derivatized) - 70eV, Positive | splash10-05fr-0790000000-546566c77f735621458e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate GC-MS (1 TMS) - 70eV, Positive | splash10-00dm-5390000000-84739ec48a42b66e5594 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 10V, Positive-QTOF | splash10-00di-0190000000-1e13429db4d85040c54d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 20V, Positive-QTOF | splash10-00dl-1960000000-4b218f0b564a1657e43f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 40V, Positive-QTOF | splash10-0729-4900000000-3cb11ab02839a3aabf06 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 10V, Negative-QTOF | splash10-000i-0190000000-f1990d4a97b412cc36b0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 20V, Negative-QTOF | splash10-00ku-0790000000-29bb631a9b0a887069fd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 40V, Negative-QTOF | splash10-03xs-1900000000-4fabb2bb92e441555d5b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 10V, Positive-QTOF | splash10-000i-0090000000-cc5b267c35e4cc81ce2d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 20V, Positive-QTOF | splash10-000f-0980000000-d08ea794055c7d924773 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 40V, Positive-QTOF | splash10-0a4i-3900000000-e096e3d21a4e3906168e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 10V, Negative-QTOF | splash10-000l-0590000000-26899881860df02e938a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 20V, Negative-QTOF | splash10-03fr-0900000000-515bec14a141b2c91d89 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 40V, Negative-QTOF | splash10-01t9-1900000000-e4f8a20c79574252d009 | 2021-09-23 | Wishart Lab | View Spectrum |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- 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 ]
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