Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 05:13:34 UTC |
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Updated at | 2022-09-11 05:13:35 UTC |
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NP-MRD ID | NP0310134 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid |
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Description | 4-O-beta-D-glucosyl-trans-sinapic acid, also known as 4-O-(b-D-glucopyranosyl)-(2E)-sinapate or sinapoyl-4-O-beta-D-glucoside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid is found in Brassica napus, Cydonia oblonga and Salacia chinensis. It was first documented in 2022 (PMID: 36122129). Based on a literature review a significant number of articles have been published on 4-O-beta-D-glucosyl-trans-sinapic acid (PMID: 36122121) (PMID: 36123115) (PMID: 36122940) (PMID: 36122933). |
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Structure | COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O InChI=1S/C17H22O10/c1-24-9-5-8(3-4-12(19)20)6-10(25-2)16(9)27-17-15(23)14(22)13(21)11(7-18)26-17/h3-6,11,13-15,17-18,21-23H,7H2,1-2H3,(H,19,20)/b4-3+/t11-,13-,14+,15-,17+/m1/s1 |
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Synonyms | Value | Source |
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4-O-(beta-D-Glucopyranosyl)-(2E)-sinapic acid | ChEBI | 4-O-(beta-D-Glucosyl)-(2E)-sinapic acid | ChEBI | O(4)-(beta-D-Glucosyl)-(2E)-sinapic acid | ChEBI | Sinapoyl-4-O-beta-D-glucoside | ChEBI | 4-O-(b-D-Glucopyranosyl)-(2E)-sinapate | Generator | 4-O-(b-D-Glucopyranosyl)-(2E)-sinapic acid | Generator | 4-O-(beta-D-Glucopyranosyl)-(2E)-sinapate | Generator | 4-O-(Β-D-glucopyranosyl)-(2E)-sinapate | Generator | 4-O-(Β-D-glucopyranosyl)-(2E)-sinapic acid | Generator | 4-O-(b-D-Glucosyl)-(2E)-sinapate | Generator | 4-O-(b-D-Glucosyl)-(2E)-sinapic acid | Generator | 4-O-(beta-D-Glucosyl)-(2E)-sinapate | Generator | 4-O-(Β-D-glucosyl)-(2E)-sinapate | Generator | 4-O-(Β-D-glucosyl)-(2E)-sinapic acid | Generator | O(4)-(b-D-Glucosyl)-(2E)-sinapate | Generator | O(4)-(b-D-Glucosyl)-(2E)-sinapic acid | Generator | O(4)-(beta-D-Glucosyl)-(2E)-sinapate | Generator | O(4)-(Β-D-glucosyl)-(2E)-sinapate | Generator | O(4)-(Β-D-glucosyl)-(2E)-sinapic acid | Generator | Sinapoyl-4-O-b-D-glucoside | Generator | Sinapoyl-4-O-β-D-glucoside | Generator | 4-O-b-D-Glucosyl-trans-sinapate | Generator | 4-O-b-D-Glucosyl-trans-sinapic acid | Generator | 4-O-beta-D-Glucosyl-trans-sinapate | Generator | 4-O-Β-D-glucosyl-trans-sinapate | Generator | 4-O-Β-D-glucosyl-trans-sinapic acid | Generator |
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Chemical Formula | C17H22O10 |
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Average Mass | 386.3530 Da |
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Monoisotopic Mass | 386.12130 Da |
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IUPAC Name | (2E)-3-(3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid |
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Traditional Name | (2E)-3-(3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C17H22O10/c1-24-9-5-8(3-4-12(19)20)6-10(25-2)16(9)27-17-15(23)14(22)13(21)11(7-18)26-17/h3-6,11,13-15,17-18,21-23H,7H2,1-2H3,(H,19,20)/b4-3+/t11-,13-,14+,15-,17+/m1/s1 |
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InChI Key | KKLWTTVTWMTNBP-KYXYLJOWSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | 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 phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Phenolic glycosides |
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Alternative Parents | |
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Substituents | - Phenolic glycoside
- Hexose monosaccharide
- Coumaric acid or derivatives
- Cinnamic acid or derivatives
- Cinnamic acid
- O-glycosyl compound
- M-dimethoxybenzene
- Dimethoxybenzene
- Phenoxy compound
- Phenol ether
- Anisole
- Styrene
- Methoxybenzene
- Alkyl aryl ether
- Monocyclic benzene moiety
- Oxane
- Benzenoid
- Monosaccharide
- Secondary alcohol
- Acetal
- Oxacycle
- Carboxylic acid derivative
- Carboxylic acid
- Organoheterocyclic compound
- Polyol
- Monocarboxylic acid or derivatives
- Ether
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Carbonyl group
- Organic oxide
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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