Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:56:11 UTC |
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Updated at | 2021-11-26 17:46:26 UTC |
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NP-MRD ID | NP0044191 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Gastrodin |
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Description | Gastrodin 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. Gastrodin is found in Anoectochilus formosanus, Anoectochilus koshunensis, Bletilla formosana, Citrullus colocynthis, Citrullus colocynthis (L.) , Cremastra appendiculata, Cyrtosia septentrionalis, Galeola faberi, Gastrodia elata , Gymnadenia conopsea, Helicia cochinchinensis, Dactylorhiza hatagirea, Origanum vulgare , Pyrus bourgaeana and Sicana odorifera. It was first documented in 2021 (PMID: 34685754). Based on a literature review a significant number of articles have been published on Gastrodin (PMID: 34718133) (PMID: 34603025) (PMID: 34581069) (PMID: 34541406). |
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Structure | OC[C@H]1O[C@@H](OC2=CC=C(CO)C=C2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C13H18O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1 |
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Synonyms | Value | Source |
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4-(Hydroxymethyl)phenyl-beta-D-glucopyranoside | Kegg | 4-(Hydroxymethyl)phenyl-b-D-glucopyranoside | Generator | 4-(Hydroxymethyl)phenyl-β-D-glucopyranoside | Generator | Gastrodine | MeSH |
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Chemical Formula | C13H18O7 |
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Average Mass | 286.2800 Da |
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Monoisotopic Mass | 286.10525 Da |
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IUPAC Name | (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol |
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Traditional Name | gastrodin |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](OC2=CC=C(CO)C=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C13H18O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1 |
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InChI Key | PUQSUZTXKPLAPR-UJPOAAIJSA-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
- Phenoxy compound
- Benzyl alcohol
- Phenol ether
- Monocyclic benzene moiety
- Monosaccharide
- Oxane
- Benzenoid
- Secondary alcohol
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Alcohol
- Hydrocarbon derivative
- Primary alcohol
- Aromatic alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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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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General References | - Bayan N, Yazdanpanah N, Rezaei N: Role of toll-like receptor 4 in diabetic retinopathy. Pharmacol Res. 2022 Jan;175:105960. doi: 10.1016/j.phrs.2021.105960. Epub 2021 Oct 28. [PubMed:34718133 ]
- Ting HC, Yang HI, Harn HJ, Chiu IM, Su HL, Li X, Chen MF, Ho TJ, Liu CA, Tsai YJ, Chiou TW, Lin SZ, Chang CY: Coactivation of GSK3beta and IGF-1 Attenuates Amyotrophic Lateral Sclerosis Nerve Fiber Cytopathies in SOD1 Mutant Patient-Derived Motor Neurons. Cells. 2021 Oct 16;10(10). pii: cells10102773. doi: 10.3390/cells10102773. [PubMed:34685754 ]
- Bai Y, Mo K, Wang G, Chen W, Zhang W, Guo Y, Sun Z: Intervention of Gastrodin in Type 2 Diabetes Mellitus and Its Mechanism. Front Pharmacol. 2021 Sep 16;12:710722. doi: 10.3389/fphar.2021.710722. eCollection 2021. [PubMed:34603025 ]
- Yan Y, Zhang YL, Jin XL, Liao X, Gong X, Chen WJ, Wei JJ, Fan XM, Piao JZ, Fu GJ, Guo CL: [Systematic review and Meta-analysis of efficacy and safety of gastrodin in treatment of tension-type headache]. Zhongguo Zhong Yao Za Zhi. 2021 Sep;46(18):4615-4622. doi: 10.19540/j.cnki.cjcmm.20210615.501. [PubMed:34581069 ]
- Yang H, Li Q, Li L, Chen S, Zhao Y, Hu Y, Wang L, Lan X, Zhong L, Lu D: Gastrodin modified polyurethane conduit promotes nerve repair via optimizing Schwann cells function. Bioact Mater. 2021 Jul 2;8:355-367. doi: 10.1016/j.bioactmat.2021.06.020. eCollection 2022 Feb. [PubMed:34541406 ]
- Chae, Sung-Wook et al. (2008). Three Phenolic Glycosides from Gastrodia elata. Journal of Applied Biological Chemistry, Volume 51 Issue 2, Pages.61-65 (2008). DOI: 10.3839/jabc.2008.011. Journal of Applied Biological Chemistry.
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