Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 16:07:07 UTC |
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Updated at | 2022-09-12 16:07:07 UTC |
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NP-MRD ID | NP0330607 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one |
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Description | Acovenosigenin belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. 4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one is found in Streptocaulon juventas. It was first documented in 2003 (PMID: 14640513). Based on a literature review a small amount of articles have been published on Acovenosigenin (PMID: 31250411) (PMID: 25555472) (PMID: 23286880) (PMID: 17510995). |
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Structure | C[C@]12CCC3C(CC[C@@H]4C[C@@H](O)C[C@@H](O)[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1 InChI=1S/C23H34O5/c1-21-7-5-17-18(4-3-14-10-15(24)11-19(25)22(14,17)2)23(21,27)8-6-16(21)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15-,16-,17?,18?,19-,21-,22+,23+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C23H34O5 |
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Average Mass | 390.5200 Da |
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Monoisotopic Mass | 390.24062 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 | C[C@]12CCC3C(CC[C@@H]4C[C@@H](O)C[C@@H](O)[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1 |
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InChI Identifier | InChI=1S/C23H34O5/c1-21-7-5-17-18(4-3-14-10-15(24)11-19(25)22(14,17)2)23(21,27)8-6-16(21)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15-,16-,17?,18?,19-,21-,22+,23+/m1/s1 |
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InChI Key | CSKIDXJFNAYMTR-YTAKEYINSA-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 cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroid lactones |
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Direct Parent | Cardenolides and derivatives |
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Alternative Parents | |
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Substituents | - Cardanolide-skeleton
- 3-hydroxysteroid
- 1-hydroxysteroid
- 3-beta-hydroxysteroid
- 14-hydroxysteroid
- Hydroxysteroid
- 2-furanone
- Cyclic alcohol
- Dihydrofuran
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tertiary alcohol
- Carboxylic acid ester
- Secondary alcohol
- Lactone
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic 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 | - Pecio L, Hassan EM, Omer EA, Gajek G, Kontek R, Sobieraj A, Stochmal A, Oleszek W: Cytotoxic Cardenolides from the Leaves of Acokanthera oblongifolia. Planta Med. 2019 Aug;85(11-12):965-972. doi: 10.1055/a-0958-2566. Epub 2019 Jun 27. [PubMed:31250411 ]
- Xue R, Han N, Xia M, Ye C, Hao Z, Wang L, Wang Y, Yang J, Saiki I, Yin J: TXA9, a cardiac glycoside from Streptocaulon juventas, exerts a potent anti-tumor activity against human non-small cell lung cancer cells in vitro and in vivo. Steroids. 2015 Feb;94:51-9. doi: 10.1016/j.steroids.2014.12.015. Epub 2014 Dec 30. [PubMed:25555472 ]
- Xue R, Han N, Ye C, Wang HB, Yin J: Cardenolide glycosides from root of Streptocaulon juventas. Phytochemistry. 2013 Apr;88:105-11. doi: 10.1016/j.phytochem.2012.12.004. Epub 2012 Dec 31. [PubMed:23286880 ]
- Zhang XH, Zhu HL, Yu Q, Xuan LJ: Cytotoxic cardenolides from Streptocaulon griffithii. Chem Biodivers. 2007 May;4(5):998-1002. doi: 10.1002/cbdv.200790091. [PubMed:17510995 ]
- Ueda JY, Tezuka Y, Banskota AH, Tran QL, Tran QK, Saiki I, Kadota S: Constituents of the Vietnamese medicinal plant Streptocaulon juventas and their antiproliferative activity against the human HT-1080 fibrosarcoma cell line. J Nat Prod. 2003 Nov;66(11):1427-33. doi: 10.1021/np030177h. [PubMed:14640513 ]
- LOTUS database [Link]
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