Record Information |
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Version | 1.0 |
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Created at | 2023-07-17 20:14:17 UTC |
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Updated at | 2024-04-19 09:49:40 UTC |
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NP-MRD ID | NP0331728 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Benzoic acid, 2-[[2-(β-D-glucopyranosyloxy)-5-hydroxybenzoyl] amino]-4-hydroxy-3-methoxy-, methyl ester |
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Description | 2-[[2-(Beta-D-Glucopyranosyloxy)-5-hydroxybenzoyl]amino]-4-hydroxy-3-methoxybenzoic acid methyl ester belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. It was first documented in 2002 (PMID: 33651529). Based on a literature review very few articles have been published on 2-[[2-(beta-D-Glucopyranosyloxy)-5-hydroxybenzoyl]amino]-4-hydroxy-3-methoxybenzoic acid methyl ester (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454). |
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Structure | [H]OC1=C([H])C([H])=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])C(=C1[H])C(=O)N([H])C1=C(C([H])=C([H])C(O[H])=C1OC([H])([H])[H])C(=O)OC([H])([H])[H] InChI=1S/C22H25NO12/c1-32-19-12(26)5-4-10(21(31)33-2)15(19)23-20(30)11-7-9(25)3-6-13(11)34-22-18(29)17(28)16(27)14(8-24)35-22/h3-7,14,16-18,22,24-29H,8H2,1-2H3,(H,23,30)/t14-,16-,17+,18-,22-/m1/s1 |
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Synonyms | Value | Source |
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2-[[2-(b-D-Glucopyranosyloxy)-5-hydroxybenzoyl]amino]-4-hydroxy-3-methoxybenzoate methyl ester | Generator | 2-[[2-(b-D-Glucopyranosyloxy)-5-hydroxybenzoyl]amino]-4-hydroxy-3-methoxybenzoic acid methyl ester | Generator | 2-[[2-(beta-D-Glucopyranosyloxy)-5-hydroxybenzoyl]amino]-4-hydroxy-3-methoxybenzoate methyl ester | Generator | 2-[[2-(Β-D-glucopyranosyloxy)-5-hydroxybenzoyl]amino]-4-hydroxy-3-methoxybenzoate methyl ester | Generator | 2-[[2-(Β-D-glucopyranosyloxy)-5-hydroxybenzoyl]amino]-4-hydroxy-3-methoxybenzoic acid methyl ester | Generator |
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Chemical Formula | C22H25NO12 |
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Average Mass | 495.4370 Da |
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Monoisotopic Mass | 495.13768 Da |
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IUPAC Name | methyl 4-hydroxy-2-(5-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamido)-3-methoxybenzoate |
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Traditional Name | methyl 4-hydroxy-2-(5-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamido)-3-methoxybenzoate |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C([H])C([H])=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])C(=C1[H])C(=O)N([H])C1=C(C([H])=C([H])C(O[H])=C1OC([H])([H])[H])C(=O)OC([H])([H])[H] |
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InChI Identifier | InChI=1S/C22H25NO12/c1-32-19-12(26)5-4-10(21(31)33-2)15(19)23-20(30)11-7-9(25)3-6-13(11)34-22-18(29)17(28)16(27)14(8-24)35-22/h3-7,14,16-18,22,24-29H,8H2,1-2H3,(H,23,30)/t14-,16-,17+,18-,22-/m1/s1 |
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InChI Key | DYFYQIKBEWHCME-RMZWBFLNSA-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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HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | 1D NMR | [13C, ] NMR Spectrum (2D, 151 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CD3OD, 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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Tannins |
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Sub Class | Hydrolyzable tannins |
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Direct Parent | Hydrolyzable tannins |
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Alternative Parents | |
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Substituents | - Hydrolyzable tannin
- Phenolic glycoside
- Benzanilide
- Aromatic anilide
- Hexose monosaccharide
- P-hydroxybenzoic acid alkyl ester
- P-hydroxybenzoic acid ester
- Glycosyl compound
- M-methoxybenzoic acid or derivatives
- O-glycosyl compound
- Benzoate ester
- Methoxyphenol
- Benzamide
- Benzoic acid or derivatives
- 4-alkoxyphenol
- Methoxyaniline
- Anisole
- Phenoxy compound
- Benzoyl
- Methoxybenzene
- Phenol ether
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Monosaccharide
- Benzenoid
- Oxane
- Methyl ester
- Vinylogous amide
- Secondary carboxylic acid amide
- Carboxamide group
- Secondary alcohol
- Carboxylic acid ester
- Acetal
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Oxacycle
- Organoheterocyclic compound
- Ether
- Polyol
- Primary alcohol
- Organic oxygen compound
- Organopnictogen compound
- Alcohol
- Organic oxide
- Organic nitrogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- 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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