Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:29:26 UTC |
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Update Date | 2022-03-07 02:52:06 UTC |
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HMDB ID | HMDB0029285 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Avenanthramide 1s |
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Description | Avenanthramide 1s 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. Based on a literature review very few articles have been published on Avenanthramide 1s. |
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Structure | COC1=CC(\C=C\C(=O)NC2=CC=CC=C2C(O)=O)=CC(OC)=C1O InChI=1S/C18H17NO6/c1-24-14-9-11(10-15(25-2)17(14)21)7-8-16(20)19-13-6-4-3-5-12(13)18(22)23/h3-10,21H,1-2H3,(H,19,20)(H,22,23)/b8-7+ |
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Synonyms | Value | Source |
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N-[4-Hydroxy-3,5-dimethoxy-(e)-cinnamoyl]-anthranilic acid | HMDB | 2-{[(2E)-1-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-ylidene]amino}benzoate | HMDB |
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Chemical Formula | C18H17NO6 |
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Average Molecular Weight | 343.3307 |
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Monoisotopic Molecular Weight | 343.105587281 |
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IUPAC Name | 2-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamido]benzoic acid |
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Traditional Name | 2-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamido]benzoic acid |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(\C=C\C(=O)NC2=CC=CC=C2C(O)=O)=CC(OC)=C1O |
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InChI Identifier | InChI=1S/C18H17NO6/c1-24-14-9-11(10-15(25-2)17(14)21)7-8-16(20)19-13-6-4-3-5-12(13)18(22)23/h3-10,21H,1-2H3,(H,19,20)(H,22,23)/b8-7+ |
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InChI Key | RGFLTMLKBQWTSH-BQYQJAHWSA-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
- Cinnamic acid amide
- M-dimethoxybenzene
- Dimethoxybenzene
- Methoxyphenol
- Benzoic acid
- Anilide
- Benzoic acid or derivatives
- Phenoxy compound
- Anisole
- Benzoyl
- Styrene
- Methoxybenzene
- Phenol ether
- N-arylamide
- Alkyl aryl ether
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous amide
- Secondary carboxylic acid amide
- Carboxamide group
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Carboxylic acid
- Ether
- Organooxygen compound
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organonitrogen 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 | Not Available |
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Physical Properties |
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State | Not Available |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Avenanthramide 1s,1TMS,isomer #1 | COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C)=CC(OC)=C1O | 3301.3 | Semi standard non polar | 33892256 | Avenanthramide 1s,1TMS,isomer #2 | COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)=CC(OC)=C1O[Si](C)(C)C | 3314.4 | Semi standard non polar | 33892256 | Avenanthramide 1s,1TMS,isomer #3 | COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=CC(OC)=C1O | 3071.2 | Semi standard non polar | 33892256 | Avenanthramide 1s,2TMS,isomer #1 | COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C | 3246.1 | Semi standard non polar | 33892256 | Avenanthramide 1s,2TMS,isomer #2 | COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O | 2999.0 | Semi standard non polar | 33892256 | Avenanthramide 1s,2TMS,isomer #3 | COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C | 3037.5 | Semi standard non polar | 33892256 | Avenanthramide 1s,3TMS,isomer #1 | COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C | 3041.1 | Semi standard non polar | 33892256 | Avenanthramide 1s,3TMS,isomer #1 | COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C | 3015.1 | Standard non polar | 33892256 | Avenanthramide 1s,1TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O | 3546.7 | Semi standard non polar | 33892256 | Avenanthramide 1s,1TBDMS,isomer #2 | COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)=CC(OC)=C1O[Si](C)(C)C(C)(C)C | 3577.3 | Semi standard non polar | 33892256 | Avenanthramide 1s,1TBDMS,isomer #3 | COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O | 3357.3 | Semi standard non polar | 33892256 | Avenanthramide 1s,2TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C | 3737.4 | Semi standard non polar | 33892256 | Avenanthramide 1s,2TBDMS,isomer #2 | COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O | 3497.8 | Semi standard non polar | 33892256 | Avenanthramide 1s,2TBDMS,isomer #3 | COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C | 3552.5 | Semi standard non polar | 33892256 | Avenanthramide 1s,3TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C | 3697.5 | Semi standard non polar | 33892256 | Avenanthramide 1s,3TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C | 3500.7 | 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 - Avenanthramide 1s GC-MS (Non-derivatized) - 70eV, Positive | splash10-004r-1955000000-564736af845bb0a51278 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Avenanthramide 1s GC-MS (2 TMS) - 70eV, Positive | splash10-00di-9243700000-43632e64182dba9bc3d2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Avenanthramide 1s 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 - Avenanthramide 1s 10V, Positive-QTOF | splash10-000l-0927000000-e5d58a2a6d94e0c81805 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 20V, Positive-QTOF | splash10-000i-1921000000-47b213268a64bc7c0277 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 40V, Positive-QTOF | splash10-0f7c-5900000000-f3f4ed879aaefc57398d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 10V, Negative-QTOF | splash10-0007-0197000000-7d69fc260eea4ff9e9dd | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 20V, Negative-QTOF | splash10-000w-1291000000-055f9d8ef39d27d8a689 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 40V, Negative-QTOF | splash10-000x-6920000000-02b0a938a9a5166c0f60 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 10V, Positive-QTOF | splash10-0a6r-0694000000-66d11b75dd9029d84131 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 20V, Positive-QTOF | splash10-056r-0950000000-f0d118cd615062d02818 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 40V, Positive-QTOF | splash10-00di-1940000000-349643528b7f0a3e36c8 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 10V, Negative-QTOF | splash10-0006-0049000000-94f6ad9f0e27a9d34656 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 20V, Negative-QTOF | splash10-001i-0091000000-639f7b338d7e724c452d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Avenanthramide 1s 40V, Negative-QTOF | splash10-0006-2192000000-a4ac72f382e99750095d | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - Bratt K, Sunnerheim K, Bryngelsson S, Fagerlund A, Engman L, Andersson RE, Dimberg LH: Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships. J Agric Food Chem. 2003 Jan 29;51(3):594-600. [PubMed:12537428 ]
- Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]
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