Record Information |
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Version | 1.0 |
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Created at | 2021-01-06 07:08:21 UTC |
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Updated at | 2021-07-15 17:37:35 UTC |
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NP-MRD ID | NP0021893 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Armillaridin |
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Provided By | NPAtlas![NPAtlas Logo](/attributions/npatlas_logo_square_small.png) |
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Description | Armillaridin is found in Armillaria mellea and Armillaria ostoyae. It was first documented in 1984 (PMID: 6548820). Based on a literature review a significant number of articles have been published on Armillaridin (PMID: 31488037) (PMID: 28632913) (PMID: 27592257) (PMID: 26952552). |
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Structure | [H]OC1=C(C(=O)O[C@]2([H])C([H])([H])[C@]3(C([H])([H])[H])[C@@]4([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[C@@]4([H])C([H])=C(C([H])=O)[C@]23O[H])C(=C(Cl)C(OC([H])([H])[H])=C1[H])C([H])([H])[H] InChI=1S/C24H29ClO6/c1-12-19(16(27)7-17(30-5)20(12)25)21(28)31-18-10-23(4)15-9-22(2,3)8-13(15)6-14(11-26)24(18,23)29/h6-7,11,13,15,18,27,29H,8-10H2,1-5H3/t13-,15+,18-,23-,24+/m1/s1 |
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Synonyms | Value | Source |
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(2R,2AS,4as,7as,7BR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoic acid | Generator |
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Chemical Formula | C24H29ClO6 |
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Average Mass | 448.9400 Da |
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Monoisotopic Mass | 448.16527 Da |
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IUPAC Name | (2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate |
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Traditional Name | (2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate |
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CAS Registry Number | Not Available |
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SMILES | COC1=C(Cl)C(C)=C(C(=O)O[C@@H]2C[C@]3(C)[C@H]4CC(C)(C)C[C@H]4C=C(C=O)[C@]23O)C(O)=C1 |
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InChI Identifier | InChI=1S/C24H29ClO6/c1-12-19(16(27)7-17(30-5)20(12)25)21(28)31-18-10-23(4)15-9-22(2,3)8-13(15)6-14(11-26)24(18,23)29/h6-7,11,13,15,18,27,29H,8-10H2,1-5H3/t13-,15+,18-,23-,24+/m1/s1 |
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InChI Key | QETHRCCHQRWBIJ-OXKPQTCESA-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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Classification | Not classified |
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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 | - Yang JS, Chen YW, Feng XZ, Yu DQ, Liang XT: Chemical constituents of Armillaria mellea mycelium. I. Isolation and characterization of armillarin and armillaridin. Planta Med. 1984 Aug;50(4):288-90. doi: 10.1055/s-2007-969711. [PubMed:6548820 ]
- Leu YS, Chen YJ, Chen CC, Huang HL: Induction of Autophagic Death of Human Hepatocellular Carcinoma Cells by Armillaridin from Armillaria mellea. Am J Chin Med. 2019;47(6):1365-1380. doi: 10.1142/S0192415X19500708. Epub 2019 Sep 5. [PubMed:31488037 ]
- Hovey MT, Cohen DT, Walden DM, Cheong PH, Scheidt KA: A Carbene Catalysis Strategy for the Synthesis of Protoilludane Natural Products. Angew Chem Int Ed Engl. 2017 Aug 7;56(33):9864-9867. doi: 10.1002/anie.201705308. Epub 2017 Jul 17. [PubMed:28632913 ]
- Chang WH, Huang HL, Huang WP, Chen CC, Chen YJ: Armillaridin induces autophagy-associated cell death in human chronic myelogenous leukemia K562 cells. Tumour Biol. 2016 Oct;37(10):14291-14300. doi: 10.1007/s13277-016-5208-6. Epub 2016 Sep 3. [PubMed:27592257 ]
- Li Z, Wang Y, Jiang B, Li W, Zheng L, Yang X, Bao Y, Sun L, Huang Y, Li Y: Structure, cytotoxic activity and mechanism of protoilludane sesquiterpene aryl esters from the mycelium of Armillaria mellea. J Ethnopharmacol. 2016 May 26;184:119-27. doi: 10.1016/j.jep.2016.02.044. Epub 2016 Mar 4. [PubMed:26952552 ]
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