| Record Information |
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| Version | 2.0 |
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| Created at | 2021-06-19 22:29:44 UTC |
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| Updated at | 2021-06-29 23:59:57 UTC |
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| NP-MRD ID | NP0031407 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | delta1-lupenone |
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| Provided By | JEOL Database |
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| Description | Glochidone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. delta1-lupenone is found in Byrsonima microphylla, Glochidion eriocarpum, Glochidion zeylanicum, Phyllanthus flexuosus, Phyllanthus sellowianus and Phyllanthus taxodiifolius. delta1-lupenone was first documented in 2003 (PMID: 15615412). Based on a literature review a significant number of articles have been published on glochidone (PMID: 22536331) (PMID: 31815547) (PMID: 19521844) (PMID: 19122328) (PMID: 16450297). |
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| Structure | [H]C([H])=C(C([H])([H])[H])[C@]1([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@]4([H])[C@]5(C([H])=C([H])C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@]5([H])C([H])([H])C([H])([H])[C@@]34C([H])([H])[H])C([H])([H])[H])[C@@]12[H] InChI=1S/C30H46O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h13,15,20-23,25H,1,9-12,14,16-18H2,2-8H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C30H46O |
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| Average Mass | 422.6970 Da |
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| Monoisotopic Mass | 422.35487 Da |
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| IUPAC Name | (1R,2R,5R,8R,9R,10R,13R,14R,19R)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-15-en-17-one |
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| Traditional Name | (1R,2R,5R,8R,9R,10R,13R,14R,19R)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-15-en-17-one |
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| CAS Registry Number | Not Available |
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| SMILES | [H]C([H])=C(C([H])([H])[H])[C@]1([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@]4([H])[C@]5(C([H])=C([H])C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@]5([H])C([H])([H])C([H])([H])[C@@]34C([H])([H])[H])C([H])([H])[H])[C@@]12[H] |
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| InChI Identifier | InChI=1S/C30H46O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h13,15,20-23,25H,1,9-12,14,16-18H2,2-8H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1 |
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| InChI Key | FWBYBHVDDGVPDF-BHMAJAPKSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Species Where Detected | |
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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 | - Gao LM, Wei XM, He YQ: [Studies on chemical constituents of Clerodendrum bungei]. Zhongguo Zhong Yao Za Zhi. 2003 Nov;28(11):1042-4. [PubMed:15615412 ]
- Ramasamy S, Abdul Wahab N, Zainal Abidin N, Manickam S, Zakaria Z: Growth inhibition of human gynecologic and colon cancer cells by Phyllanthus watsonii through apoptosis induction. PLoS One. 2012;7(4):e34793. doi: 10.1371/journal.pone.0034793. Epub 2012 Apr 20. [PubMed:22536331 ]
- Sichaem J, Vo HC, Nha-Tran T, Jarupinthusophon S, Niamnont N, Srikittiwanna K, Nguyen TK, Tran TN, Le TT, Duong TH: 29-Norlupane-1beta-hydroxy-3,20-dione, a new norlupane triterpenoid from the twigs and leaves of Phyllanthus acidus. Nat Prod Res. 2019 Dec 9:1-6. doi: 10.1080/14786419.2019.1700252. [PubMed:31815547 ]
- Catapan E, Moreno FN, Luis Busi da Silva M, Otuki MF, Niero R, Filho VC, Augusto Yunes R, Viana AM: Protocols for in vitro culture and phytochemical analysis of Phyllanthus species (euphorbiaceae). Methods Mol Biol. 2009;547:167-77. doi: 10.1007/978-1-60327-287-2_14. [PubMed:19521844 ]
- Kiem PV, Thu VK, Yen PH, Nhiem NX, Tung NH, Cuong NX, Minh CV, Huong HT, Hyun JH, Kang HK, Kim YH: New triterpenoid saponins from Glochidion eriocarpum and their cytotoxic activity. Chem Pharm Bull (Tokyo). 2009 Jan;57(1):102-5. doi: 10.1248/cpb.57.102. [PubMed:19122328 ]
- Tuchinda P, Kumkao A, Pohmakotr M, Sophasan S, Santisuk T, Reutrakul V: Cytotoxic arylnaphthalide lignan glycosides from the aerial parts of Phyllanthus taxodiifolius. Planta Med. 2006 Jan;72(1):60-2. doi: 10.1055/s-2005-873141. [PubMed:16450297 ]
- Aguiar, R. M., et al. (2005). Aguiar, R. M., et al, Phytochemistry 66, 2388 (2005) . Phytochem..
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