Record Information |
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Version | 1.0 |
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Created at | 2021-06-21 00:45:48 UTC |
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Updated at | 2021-06-30 00:18:56 UTC |
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NP-MRD ID | NP0043322 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | simplextone D |
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Provided By | JEOL Database![JEOL Logo](/attributions/jeol_logo.png) |
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Description | Simplextone D belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. simplextone D is found in Plakortis simplex. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on Simplextone D (PMID: 27466641) (PMID: 28467388) (PMID: 23806071) (PMID: 27253005). |
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Structure | [H]O[C@@]1([H])C([H])([H])C(=O)O[C@@]1(C([H])([H])C([H])([H])[H])[C@@]1([H])[C@]([H])(C([H])([H])C([H])([H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@]1(O[H])C([H])([H])C([H])([H])[H] InChI=1S/C17H30O4/c1-5-8-12-11(4)10-16(20,6-2)15(12)17(7-3)13(18)9-14(19)21-17/h11-13,15,18,20H,5-10H2,1-4H3/t11-,12+,13-,15-,16+,17+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C17H30O4 |
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Average Mass | 298.4230 Da |
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Monoisotopic Mass | 298.21441 Da |
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IUPAC Name | (4S,5S)-5-ethyl-5-[(1S,2R,4S,5R)-2-ethyl-2-hydroxy-4-methyl-5-propylcyclopentyl]-4-hydroxyoxolan-2-one |
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Traditional Name | (4S,5S)-5-ethyl-5-[(1S,2R,4S,5R)-2-ethyl-2-hydroxy-4-methyl-5-propylcyclopentyl]-4-hydroxyoxolan-2-one |
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CAS Registry Number | Not Available |
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SMILES | [H]O[C@@]1([H])C([H])([H])C(=O)O[C@@]1(C([H])([H])C([H])([H])[H])[C@@]1([H])[C@]([H])(C([H])([H])C([H])([H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@]1(O[H])C([H])([H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C17H30O4/c1-5-8-12-11(4)10-16(20,6-2)15(12)17(7-3)13(18)9-14(19)21-17/h11-13,15,18,20H,5-10H2,1-4H3/t11-,12+,13-,15-,16+,17+/m0/s1 |
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InChI Key | BSZWGEKCCWIUCC-FGBAQLTPSA-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, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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 | Species Name | Source | Reference |
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Plakortis simplex | JEOL database | - Zhang, J., et al, J. Nat. Prod. 76, 600 (2013)
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene lactones |
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Direct Parent | Terpene lactones |
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Alternative Parents | |
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Substituents | - Terpene lactone
- 11-noriridane monoterpenoid
- Monocyclic monoterpenoid
- Monoterpenoid
- Cyclopentanol
- Gamma butyrolactone
- Cyclic alcohol
- Tetrahydrofuran
- Tertiary alcohol
- Lactone
- Carboxylic acid ester
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic 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 | - Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
- Li J, Li C, Riccio R, Lauro G, Bifulco G, Li TJ, Tang H, Zhuang CL, Ma H, Sun P, Zhang W: Chemistry and Selective Tumor Cell Growth Inhibitory Activity of Polyketides from the South China Sea Sponge Plakortis sp. Mar Drugs. 2017 May 3;15(5). pii: md15050129. doi: 10.3390/md15050129. [PubMed:28467388 ]
- Zhang J, Tang X, Li J, Li P, de Voogd NJ, Ni X, Jin X, Yao X, Li P, Li G: Cytotoxic polyketide derivatives from the South China Sea sponge Plakortis simplex. J Nat Prod. 2013 Apr 26;76(4):600-6. doi: 10.1021/np300771p. Epub 2013 Mar 25. [PubMed:23806071 ]
- Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
- Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
- Zhang, J., et al. (2013). Zhang, J., et al, J. Nat. Prod. 76, 600 (2013). J. Nat. Prod..
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