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 02:44:00 UTC |
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Update Date | 2022-03-07 02:56:52 UTC |
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HMDB ID | HMDB0041088 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (E)-Squamosamide |
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Description | (E)-Squamosamide belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids (E)-Squamosamide has been detected, but not quantified in, fruits. This could make (e)-squamosamide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E)-Squamosamide. |
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Structure | COC1=CC(\C=C(/C(=O)NCCC2=CC=C(O)C=C2)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O InChI=1S/C26H27NO7/c1-32-22-13-17(6-9-21(22)29)12-20(18-14-23(33-2)25(30)24(15-18)34-3)26(31)27-11-10-16-4-7-19(28)8-5-16/h4-9,12-15,28-30H,10-11H2,1-3H3,(H,27,31)/b20-12- |
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Synonyms | Value | Source |
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Squamosamide | HMDB | (2Z)-2-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidate | Generator | FLZ Compound | MeSH |
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Chemical Formula | C26H27NO7 |
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Average Molecular Weight | 465.4951 |
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Monoisotopic Molecular Weight | 465.178752223 |
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IUPAC Name | (2Z)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide |
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Traditional Name | (2Z)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide |
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CAS Registry Number | 142750-35-4 |
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SMILES | COC1=CC(\C=C(/C(=O)NCCC2=CC=C(O)C=C2)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O |
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InChI Identifier | InChI=1S/C26H27NO7/c1-32-22-13-17(6-9-21(22)29)12-20(18-14-23(33-2)25(30)24(15-18)34-3)26(31)27-11-10-16-4-7-19(28)8-5-16/h4-9,12-15,28-30H,10-11H2,1-3H3,(H,27,31)/b20-12- |
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InChI Key | VEUGFVRUMOLGFJ-NDENLUEZSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Stilbenes |
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Sub Class | Not Available |
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Direct Parent | Stilbenes |
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Alternative Parents | |
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Substituents | - Stilbene
- Cinnamic acid amide
- Cinnamic acid or derivatives
- Hydroxycinnamic acid or derivatives
- Methoxyphenol
- Phenylacetamide
- Dimethoxybenzene
- M-dimethoxybenzene
- Methoxybenzene
- Anisole
- Styrene
- Phenoxy compound
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Carboxamide group
- Secondary carboxylic acid amide
- Ether
- Carboxylic acid derivative
- Organic oxide
- Organic oxygen compound
- Organic nitrogen compound
- Organopnictogen compound
- Carbonyl group
- Hydrocarbon derivative
- Organooxygen compound
- 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 | |
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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 | 206 - 207 °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)-Squamosamide,1TMS,isomer #1 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O[Si](C)(C)C)C=C2)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O | 4470.5 | Semi standard non polar | 33892256 | (E)-Squamosamide,1TMS,isomer #2 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O)C=C2)C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O | 4459.1 | Semi standard non polar | 33892256 | (E)-Squamosamide,1TMS,isomer #3 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O)C=C2)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O[Si](C)(C)C | 4511.3 | Semi standard non polar | 33892256 | (E)-Squamosamide,1TMS,isomer #4 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O | 4347.5 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TMS,isomer #1 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O[Si](C)(C)C)C=C2)C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O | 4362.6 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TMS,isomer #2 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O[Si](C)(C)C)C=C2)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O[Si](C)(C)C | 4404.9 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TMS,isomer #3 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O | 4200.0 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TMS,isomer #4 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O)C=C2)C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C | 4311.0 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TMS,isomer #5 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C)C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O | 4180.7 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TMS,isomer #6 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O[Si](C)(C)C | 4204.8 | Semi standard non polar | 33892256 | (E)-Squamosamide,3TMS,isomer #1 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O[Si](C)(C)C)C=C2)C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C | 4317.6 | Semi standard non polar | 33892256 | (E)-Squamosamide,3TMS,isomer #2 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O | 4155.4 | Semi standard non polar | 33892256 | (E)-Squamosamide,3TMS,isomer #3 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O[Si](C)(C)C | 4185.9 | Semi standard non polar | 33892256 | (E)-Squamosamide,3TMS,isomer #4 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C)C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C | 4107.5 | Semi standard non polar | 33892256 | (E)-Squamosamide,4TMS,isomer #1 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C | 4179.2 | Semi standard non polar | 33892256 | (E)-Squamosamide,4TMS,isomer #1 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C | 3311.1 | Standard non polar | 33892256 | (E)-Squamosamide,1TBDMS,isomer #1 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O | 4765.6 | Semi standard non polar | 33892256 | (E)-Squamosamide,1TBDMS,isomer #2 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O)C=C2)C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O | 4736.2 | Semi standard non polar | 33892256 | (E)-Squamosamide,1TBDMS,isomer #3 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O)C=C2)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 4779.6 | Semi standard non polar | 33892256 | (E)-Squamosamide,1TBDMS,isomer #4 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O | 4580.3 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TBDMS,isomer #1 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O | 4910.9 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TBDMS,isomer #2 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 4943.3 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TBDMS,isomer #3 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O | 4710.5 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TBDMS,isomer #4 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O)C=C2)C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 4879.3 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TBDMS,isomer #5 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O | 4694.6 | Semi standard non polar | 33892256 | (E)-Squamosamide,2TBDMS,isomer #6 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 4722.1 | Semi standard non polar | 33892256 | (E)-Squamosamide,3TBDMS,isomer #1 | COC1=CC(/C=C(\C(=O)NCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 5070.4 | Semi standard non polar | 33892256 | (E)-Squamosamide,3TBDMS,isomer #2 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O | 4870.8 | Semi standard non polar | 33892256 | (E)-Squamosamide,3TBDMS,isomer #3 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 4893.7 | Semi standard non polar | 33892256 | (E)-Squamosamide,3TBDMS,isomer #4 | COC1=CC(/C=C(\C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 4823.6 | Semi 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)-Squamosamide GC-MS (Non-derivatized) - 70eV, Positive | splash10-0zfr-1419100000-f28b388fe00d04c35d40 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (E)-Squamosamide GC-MS (3 TMS) - 70eV, Positive | splash10-014i-0100419000-01d7b0e4e83b0f52ce3f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (E)-Squamosamide 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)-Squamosamide 10V, Positive-QTOF | splash10-016r-0306900000-e28caa99c43e074d3a09 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 20V, Positive-QTOF | splash10-00g0-0916400000-29ba9401ef4bd732aa22 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 40V, Positive-QTOF | splash10-0079-3911000000-d9279dc9586c452c8954 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 10V, Negative-QTOF | splash10-03di-0001900000-b8a5acbd5930380b92d9 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 20V, Negative-QTOF | splash10-08g4-0306900000-d9e1fff27090a74a98d6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 40V, Negative-QTOF | splash10-002u-2659300000-0838e6d20b4a54489b40 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 10V, Positive-QTOF | splash10-01b9-0300900000-e27576aab9b0cddd7cc9 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 20V, Positive-QTOF | splash10-01b9-0525900000-31a598287fac5323984d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 40V, Positive-QTOF | splash10-00di-2908200000-2b9799725628ac96d750 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 10V, Negative-QTOF | splash10-03di-0002900000-72c4a2633db9ea8c015a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 20V, Negative-QTOF | splash10-03fr-0308900000-90249d4dc2d495db242e | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (E)-Squamosamide 40V, Negative-QTOF | splash10-01ox-2019500000-a89c8dfebdf7c4024227 | 2021-09-25 | Wishart Lab | View Spectrum |
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