Record Information |
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Version | 2.0 |
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Created at | 2022-09-04 09:16:49 UTC |
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Updated at | 2022-09-04 09:16:50 UTC |
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NP-MRD ID | NP0192138 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-12-(4-hydroxy-2-methoxyphenyl)-5-(4-hydroxyphenyl)-2-[5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one |
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Description | Alopecurone D belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-12-(4-hydroxy-2-methoxyphenyl)-5-(4-hydroxyphenyl)-2-[5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one is found in Sophora alopecuroides. It was first documented in 2020 (PMID: 31442619). Based on a literature review a significant number of articles have been published on Alopecurone D (PMID: 36068077) (PMID: 36068076) (PMID: 36068075) (PMID: 36068074). |
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Structure | COC1=CC(O)=CC=C1[C@@H]1CC(=O)C2=C(O)C3=C(O[C@@H]([C@H]3C3=CC(O)=CC(O)=C3)C3=CC=C(O)C=C3)C(CC(CC=C(C)C)C(C)=C)=C2O1 InChI=1S/C40H40O9/c1-20(2)6-7-23(21(3)4)16-30-39-35(31(45)19-33(48-39)29-13-12-26(42)18-32(29)47-5)37(46)36-34(24-14-27(43)17-28(44)15-24)38(49-40(30)36)22-8-10-25(41)11-9-22/h6,8-15,17-18,23,33-34,38,41-44,46H,3,7,16,19H2,1-2,4-5H3/t23?,33-,34-,38+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C40H40O9 |
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Average Mass | 664.7510 Da |
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Monoisotopic Mass | 664.26723 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(O)=CC=C1[C@@H]1CC(=O)C2=C(O)C3=C(O[C@@H]([C@H]3C3=CC(O)=CC(O)=C3)C3=CC=C(O)C=C3)C(CC(CC=C(C)C)C(C)=C)=C2O1 |
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InChI Identifier | InChI=1S/C40H40O9/c1-20(2)6-7-23(21(3)4)16-30-39-35(31(45)19-33(48-39)29-13-12-26(42)18-32(29)47-5)37(46)36-34(24-14-27(43)17-28(44)15-24)38(49-40(30)36)22-8-10-25(41)11-9-22/h6,8-15,17-18,23,33-34,38,41-44,46H,3,7,16,19H2,1-2,4-5H3/t23?,33-,34-,38+/m0/s1 |
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InChI Key | QXJNTDXKZVNKDH-CYXBZXPJSA-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 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | 2-arylbenzofuran flavonoids |
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Sub Class | Not Available |
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Direct Parent | 2-arylbenzofuran flavonoids |
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Alternative Parents | |
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Substituents | - 2-arylbenzofuran flavonoid
- 8-prenylated flavanone
- 7-prenylated 2-arybenzofuran
- 8-prenylated flavan
- Linear 1,7-diphenylheptane skeleton
- Furanoflavonoid or dihydroflavonoid
- 2p-methoxyflavonoid-skeleton
- Flavanone
- 4'-hydroxyflavonoid
- Neolignan skeleton
- Hydroxyflavonoid
- 5-hydroxyflavonoid
- Flavan
- 1-phenylcoumaran
- Furanochromone
- Stilbene
- Chromone
- Benzopyran
- Chromane
- Aromatic monoterpenoid
- Methoxyphenol
- Monoterpenoid
- 1-benzopyran
- Benzofuran
- Coumaran
- Phenol ether
- Phenoxy compound
- Anisole
- Methoxybenzene
- Resorcinol
- Aryl alkyl ketone
- Aryl ketone
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Vinylogous acid
- Ketone
- Organoheterocyclic compound
- Oxacycle
- Ether
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 R, Deng X, Gao Q, Wu X, Han L, Gao X, Zhao S, Chen W, Zhou R, Li Z, Bai C: Sophora alopecuroides L.: An ethnopharmacological, phytochemical, and pharmacological review. J Ethnopharmacol. 2020 Feb 10;248:112172. doi: 10.1016/j.jep.2019.112172. Epub 2019 Aug 20. [PubMed:31442619 ]
- Kazawa K, Kubo T, Akishita M, Ishii S: Long-term impact of the COVID-19 pandemic on facility- and home-dwelling people with dementia: Perspectives from professionals involved in dementia care. Geriatr Gerontol Int. 2022 Sep 6. doi: 10.1111/ggi.14465. [PubMed:36068077 ]
- Arthur JD, Alamaw ED, Jampachairsri K, Sharp P, Nagamine CM, Huss MK, Pacharinsak C: Efficacy of 3 Buprenorphine Formulations for the Attenuation of Hypersensitivity after Plantar Incision in Immunodeficient NSG Mice. J Am Assoc Lab Anim Sci. 2022 Sep 6. doi: 10.30802/AALAS-JAALAS-22-000058. [PubMed:36068076 ]
- Zhu N, Liu J, Ma T, Zhang Y, Lin Y: Fully digital versus conventional workflow for horizontal ridge augmentation with intraoral block bone: A randomized controlled clinical trial. Clin Implant Dent Relat Res. 2022 Sep 6. doi: 10.1111/cid.13129. [PubMed:36068075 ]
- Gerstle EE, O'Connor K, Keenan KG, Slavens BA, Cobb SC: The Effect of Age and Fall History on Lower Extremity Neuromuscular Function During Descent of a Single Transition Step. J Aging Phys Act. 2022 Sep 5:1-8. doi: 10.1123/japa.2021-0521. [PubMed:36068074 ]
- LOTUS database [Link]
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