Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-12 00:17:29 UTC |
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Update Date | 2022-03-07 02:56:00 UTC |
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HMDB ID | HMDB0038943 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (E)-Avenanthramide D |
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Description | (E)-Avenanthramide D belongs to the class of organic compounds known as avenanthramides. These are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid (E)-Avenanthramide D has been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and oats (Avena sativa). This could make (e)-avenanthramide D a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E)-Avenanthramide D. |
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Structure | OC(=O)C1=C(NC(=O)\C=C/C2=CC=C(O)C=C2)C=CC=C1 InChI=1S/C16H13NO4/c18-12-8-5-11(6-9-12)7-10-15(19)17-14-4-2-1-3-13(14)16(20)21/h1-10,18H,(H,17,19)(H,20,21)/b10-7- |
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Synonyms | Value | Source |
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2-{[(2Z)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}benzoate | HMDB |
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Chemical Formula | C16H13NO4 |
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Average Molecular Weight | 283.2787 |
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Monoisotopic Molecular Weight | 283.084457909 |
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IUPAC Name | 2-[(2Z)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid |
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Traditional Name | 2-[(2Z)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid |
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CAS Registry Number | Not Available |
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SMILES | OC(=O)C1=C(NC(=O)\C=C/C2=CC=C(O)C=C2)C=CC=C1 |
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InChI Identifier | InChI=1S/C16H13NO4/c18-12-8-5-11(6-9-12)7-10-15(19)17-14-4-2-1-3-13(14)16(20)21/h1-10,18H,(H,17,19)(H,20,21)/b10-7- |
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InChI Key | INBHLTYBRKASIZ-YFHOEESVSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as avenanthramides. These are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid. |
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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 | Avenanthramides |
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Alternative Parents | |
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Substituents | - Avenanthramide
- N-cinnamoylanthranilic acid
- Acylaminobenzoic acid or derivatives
- Coumaric acid or derivatives
- Cinnamic acid amide
- Benzoic acid or derivatives
- Benzoic acid
- Anilide
- Styrene
- N-arylamide
- Benzoyl
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous amide
- Secondary carboxylic acid amide
- Carboxamide group
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- 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 | |
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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 | 219 °C | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(E)-Avenanthramide D,1TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C\C1=CC=C(O)C=C1 | 2986.9 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(/C=C\C(=O)NC2=CC=CC=C2C(=O)O)C=C1 | 2985.1 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,1TMS,isomer #3 | C[Si](C)(C)N(C(=O)/C=C\C1=CC=C(O)C=C1)C1=CC=CC=C1C(=O)O | 2829.6 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1 | 2978.0 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,2TMS,isomer #2 | C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C\C1=CC=C(O)C=C1)[Si](C)(C)C | 2778.1 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,2TMS,isomer #3 | C[Si](C)(C)OC1=CC=C(/C=C\C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)C=C1 | 2826.6 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C | 2838.8 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C | 2808.2 | Standard non polar | 33892256 | (E)-Avenanthramide D,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C\C1=CC=C(O)C=C1 | 3245.9 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)NC2=CC=CC=C2C(=O)O)C=C1 | 3280.2 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(C(=O)/C=C\C1=CC=C(O)C=C1)C1=CC=CC=C1C(=O)O | 3117.6 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 3498.7 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C\C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C | 3307.3 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)C=C1 | 3373.1 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 3548.5 | Semi standard non polar | 33892256 | (E)-Avenanthramide D,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 3380.7 | Standard non polar | 33892256 |
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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 - (E)-Avenanthramide D GC-MS (Non-derivatized) - 70eV, Positive | splash10-014s-0970000000-a566f728fa7183881de4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (E)-Avenanthramide D GC-MS (2 TMS) - 70eV, Positive | splash10-01w0-5249400000-a46404a5c44e28b98c0a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (E)-Avenanthramide D 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 - (E)-Avenanthramide D 10V, Positive-QTOF | splash10-0019-0890000000-04ad40c92e259a7d11d6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 20V, Positive-QTOF | splash10-000i-1920000000-44906bb2b5721bdec1ff | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 40V, Positive-QTOF | splash10-0f79-9800000000-ad6fc6f94bf65f268a8c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 10V, Negative-QTOF | splash10-001r-0190000000-4ee1473cdcf98c48a16e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 20V, Negative-QTOF | splash10-000i-1490000000-f60605812a47a3f42c41 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 40V, Negative-QTOF | splash10-0006-8900000000-d19f83c6414c2312c761 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 10V, Negative-QTOF | splash10-001i-0090000000-0786f2d6ceb295d228c4 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 20V, Negative-QTOF | splash10-014r-1790000000-d3cc0cd017bee4c03d71 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 40V, Negative-QTOF | splash10-014i-1910000000-79dcee6fd90a20fbd59a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 10V, Positive-QTOF | splash10-0002-0900000000-061a828162cdf954fd23 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 20V, Positive-QTOF | splash10-00kb-1900000000-7a1597345127828215e4 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Avenanthramide D 40V, Positive-QTOF | splash10-014i-4900000000-9c1631c53579bbdd3f75 | 2021-09-25 | Wishart Lab | View Spectrum |
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