Record Information |
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Version | 1.0 |
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Created at | 2022-09-05 17:26:48 UTC |
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Updated at | 2022-09-05 17:26:49 UTC |
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NP-MRD ID | NP0217181 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+)-arctigenin |
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Description | (+)-Arctigenin belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. (+)-arctigenin is found in Bupleurum salicifolium, Centaurea regia, Saussurea parviflora and Wikstroemia indica. It was first documented in 2022 (PMID: 35987408). Based on a literature review a significant number of articles have been published on (+)-Arctigenin (PMID: 35847593) (PMID: 35850845) (PMID: 35779819) (PMID: 35731324). |
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Structure | COC1=CC=C(C[C@@H]2COC(=O)[C@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C21H24O6 |
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Average Mass | 372.4170 Da |
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Monoisotopic Mass | 372.15729 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC=C(C[C@@H]2COC(=O)[C@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC |
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InChI Identifier | InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m1/s1 |
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InChI Key | NQWVSMVXKMHKTF-CVEARBPZSA-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 dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Furanoid lignans |
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Sub Class | Tetrahydrofuran lignans |
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Direct Parent | Dibenzylbutyrolactone lignans |
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Alternative Parents | |
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Substituents | - Dibenzylbutyrolactone
- Lignan lactone
- Methoxyphenol
- Dimethoxybenzene
- O-dimethoxybenzene
- Phenoxy compound
- Methoxybenzene
- Anisole
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Gamma butyrolactone
- Benzenoid
- Oxolane
- Lactone
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Ether
- Oxacycle
- Carboxylic acid derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- 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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General References | - Wang Y, Li X, Pu S, Wang X, Guo L, Zhang L, Wang Z: Ameliorative Effects of Arctigenin on Pulmonary Fibrosis Induced by Bleomycin via the Antioxidant Activity. Oxid Med Cell Longev. 2022 Jul 5;2022:3541731. doi: 10.1155/2022/3541731. eCollection 2022. [PubMed:35847593 ]
- Yang L, Lyu H, Yiming A, Xu X, Ma C, Tu S, Chen B, Liu M, Wu C: Integrated metabolism, network pharmacology, and pharmacokinetics to explore the exposure differences of the pharmacodynamic material basis in vivo caused by different extraction methods for Saussurea involucrata. J Ethnopharmacol. 2022 Nov 15;298:115648. doi: 10.1016/j.jep.2022.115648. Epub 2022 Aug 18. [PubMed:35987408 ]
- Zhao ZF, Nian M, Ji XT, Lyu H, Qiao HF, Yang XH, Qian MC: [Virtual screening and antiepileptic activity evaluation of COX-2 inhibitory components in Trachelospermi Caulisetfolium]. Zhongguo Zhong Yao Za Zhi. 2022 Jul;47(14):3863-3875. doi: 10.19540/j.cnki.cjcmm.20220307.702. [PubMed:35850845 ]
- Jin Z, Sheng H, Wang S, Wang Y, Cheng Y: Network pharmacology study to reveal active compounds of Qinggan Yin formula against pulmonary inflammation by inhibiting MAPK activation. J Ethnopharmacol. 2022 Oct 5;296:115513. doi: 10.1016/j.jep.2022.115513. Epub 2022 Jun 30. [PubMed:35779819 ]
- Yuan Q, Wu Y, Wang G, Zhou X, Dong X, Lou Z, Li S, Wang D: Preventive effects of arctigenin from Arctium lappa L against LPS-induced neuroinflammation and cognitive impairments in mice. Metab Brain Dis. 2022 Aug;37(6):2039-2052. doi: 10.1007/s11011-022-01031-3. Epub 2022 Jun 22. [PubMed:35731324 ]
- LOTUS database [Link]
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