Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:48:02 UTC |
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Updated at | 2021-11-26 17:45:01 UTC |
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NP-MRD ID | NP0044063 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Siebolside A |
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Description | SIEBOLSIDE A 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. Siebolside A is found in Populus sieboldii. It was first documented in 2006 (PMID: 16933880). Based on a literature review very few articles have been published on SIEBOLSIDE A. |
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Structure | CC(=O)OC[C@H]1O[C@@H](OC2=CC(COC(=O)C3=CC=CC=C3)=CC=C2O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C22H24O10/c1-12(23)29-11-17-18(25)19(26)20(27)22(32-17)31-16-9-13(7-8-15(16)24)10-30-21(28)14-5-3-2-4-6-14/h2-9,17-20,22,24-27H,10-11H2,1H3/t17-,18-,19+,20-,22-/m1/s1 |
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Synonyms | Value | Source |
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2-Hydroxy-5-((benzoyloxy)methyl)phenyl (6'-O-acetyl) beta-D-glucopyranoside | MeSH |
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Chemical Formula | C22H24O10 |
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Average Mass | 448.4240 Da |
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Monoisotopic Mass | 448.13695 Da |
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IUPAC Name | (3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4-hydroxyphenyl)methyl benzoate |
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Traditional Name | (3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4-hydroxyphenyl)methyl benzoate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)OC[C@H]1O[C@@H](OC2=CC(COC(=O)C3=CC=CC=C3)=CC=C2O)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C22H24O10/c1-12(23)29-11-17-18(25)19(26)20(27)22(32-17)31-16-9-13(7-8-15(16)24)10-30-21(28)14-5-3-2-4-6-14/h2-9,17-20,22,24-27H,10-11H2,1H3/t17-,18-,19+,20-,22-/m1/s1 |
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InChI Key | FUCUESRRBJSDMA-OUUKCGNVSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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
- O-glycosyl compound
- Benzoate ester
- Benzyloxycarbonyl
- Benzoic acid or derivatives
- Phenoxy compound
- Benzoyl
- Phenol ether
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Monocyclic benzene moiety
- Oxane
- Monosaccharide
- Dicarboxylic acid or derivatives
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Acetal
- Carboxylic acid derivative
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Carbonyl group
- 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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