Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 21:46:43 UTC |
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Updated at | 2022-04-28 21:46:44 UTC |
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NP-MRD ID | NP0076585 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+)-Gaultherin B |
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Description | Gaultherin B belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. (+)-Gaultherin B is found in Gaultheria yunnanensis. It was first documented in 2007 (PMID: 17329839). Based on a literature review a small amount of articles have been published on Gaultherin B (PMID: 34768963) (PMID: 32744786) (PMID: 34798162) (PMID: 31398629). |
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Structure | COC1=CC(=CC(OC)=C1O)[C@@H]1[C@@H](COC(C)=O)[C@H](COC(C)=O)CC2=C1C(OC)=C(O)C(OC)=C2 InChI=1S/C26H32O10/c1-13(27)35-11-17-7-15-8-21(33-5)25(30)26(34-6)23(15)22(18(17)12-36-14(2)28)16-9-19(31-3)24(29)20(10-16)32-4/h8-10,17-18,22,29-30H,7,11-12H2,1-6H3/t17-,18-,22+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C26H32O10 |
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Average Mass | 504.5320 Da |
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Monoisotopic Mass | 504.19955 Da |
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IUPAC Name | [(2R,3R,4S)-3-[(acetyloxy)methyl]-6-hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-5,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methyl acetate |
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Traditional Name | [(2R,3R,4S)-3-[(acetyloxy)methyl]-6-hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-5,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methyl acetate |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(=CC(OC)=C1O)[C@@H]1[C@@H](COC(C)=O)[C@H](COC(C)=O)CC2=C1C(OC)=C(O)C(OC)=C2 |
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InChI Identifier | InChI=1S/C26H32O10/c1-13(27)35-11-17-7-15-8-21(33-5)25(30)26(34-6)23(15)22(18(17)12-36-14(2)28)16-9-19(31-3)24(29)20(10-16)32-4/h8-10,17-18,22,29-30H,7,11-12H2,1-6H3/t17-,18-,22+/m0/s1 |
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InChI Key | ZFEKJLMOQMMNLF-NPPFBWRTSA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Aryltetralin lignans |
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Sub Class | Not Available |
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Direct Parent | Aryltetralin lignans |
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Alternative Parents | |
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Substituents | - 1-aryltetralin lignan
- Methoxyphenol
- Tetralin
- Dimethoxybenzene
- M-dimethoxybenzene
- Anisole
- Phenoxy compound
- Phenol ether
- Methoxybenzene
- Phenol
- Alkyl aryl ether
- Dicarboxylic acid or derivatives
- Benzenoid
- Monocyclic benzene moiety
- Carboxylic acid ester
- Ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organooxygen compound
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic 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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General References | - Olszewska MA, Owczarek A, Magiera A, Granica S, Michel P: Screening for the Active Anti-Inflammatory and Antioxidant Polyphenols of Gaultheria procumbens and Their Application for Standardisation: From Identification through Cellular Studies to Quantitative Determination. Int J Mol Sci. 2021 Oct 26;22(21):11532. doi: 10.3390/ijms222111532. [PubMed:34768963 ]
- Xiang JC, Wang Q, Zhu J: Radical-Cation Cascade to Aryltetralin Cyclic Ether Lignans Under Visible-Light Photoredox Catalysis. Angew Chem Int Ed Engl. 2020 Nov 16;59(47):21195-21202. doi: 10.1002/anie.202007548. Epub 2020 Sep 11. [PubMed:32744786 ]
- Wang X, Dong Y, Song R, Yu A, Wei J, Fan Q, Yao J, Shan D, Zhong X, Lv F, She G: Intestinal metabolism and absorption mechanism of multi-components in Gaultheria leucocarpa var. yunnanensis - An assessment using in situ and in vitro models, comparing gut segments in pathological with physiological conditions. J Ethnopharmacol. 2022 Mar 25;286:114844. doi: 10.1016/j.jep.2021.114844. Epub 2021 Nov 16. [PubMed:34798162 ]
- Wang X, Li X, Wang R, Wang L, Fan S, Wang X, Xu X, Yan X, He T, Ren X, She G: Human gastrointestinal metabolism of the anti-rheumatic fraction of Dianbaizhu (Gaultheria leucocarpa var. yunnanensis) in vitro: Elucidation of the metabolic analysis in gastric juice, intestinal juice and human intestinal bacteria by UPLC-LTQ-Orbitrap-MS(n) and HPLC-DAD. J Pharm Biomed Anal. 2019 Oct 25;175:112791. doi: 10.1016/j.jpba.2019.112791. Epub 2019 Jul 26. [PubMed:31398629 ]
- Zhang B, Li JB, Zhang DM, Ding Y, Du GH: Analgesic and anti-inflammatory activities of a fraction rich in gaultherin isolated from Gaultheria yunnanensis (FRANCH.) REHDER. Biol Pharm Bull. 2007 Mar;30(3):465-9. doi: 10.1248/bpb.30.465. [PubMed:17329839 ]
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