Record Information |
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Version | 1.0 |
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Created at | 2020-10-21 16:38:18 UTC |
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Updated at | 2021-07-15 16:45:18 UTC |
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NP-MRD ID | NP0001802 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Lactone II |
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Provided By | NPAtlas |
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Description | Lactone II is found in Streptomyces sp. It was first documented in 1999 (PMID: 10513843). Based on a literature review very few articles have been published on [(3S,4S)-4-hydroxy-5-oxooxolan-3-yl]methyl (2E)-3-[(2R,3S)-3-methyloxiran-2-yl]prop-2-enoate (PMID: 30825578) (PMID: 30166552) (PMID: 22572126) (PMID: 15455149) (PMID: 12240331). |
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Structure | [H]O[C@]1([H])C(=O)OC([H])([H])[C@]1([H])C([H])([H])OC(=O)C(\[H])=C(/[H])[C@@]1([H])O[C@@]1([H])C([H])([H])[H] InChI=1S/C11H14O6/c1-6-8(17-6)2-3-9(12)15-4-7-5-16-11(14)10(7)13/h2-3,6-8,10,13H,4-5H2,1H3/b3-2+/t6-,7-,8+,10-/m0/s1 |
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Synonyms | Value | Source |
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[(3S,4S)-4-Hydroxy-5-oxooxolan-3-yl]methyl (2E)-3-[(2R,3S)-3-methyloxiran-2-yl]prop-2-enoic acid | Generator |
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Chemical Formula | C11H14O6 |
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Average Mass | 242.2270 Da |
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Monoisotopic Mass | 242.07904 Da |
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IUPAC Name | [(3S,4S)-4-hydroxy-5-oxooxolan-3-yl]methyl (2E)-3-[(2R,3S)-3-methyloxiran-2-yl]prop-2-enoate |
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Traditional Name | [(3S,4S)-4-hydroxy-5-oxooxolan-3-yl]methyl (2E)-3-[(2R,3S)-3-methyloxiran-2-yl]prop-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1O[C@@H]1\C=C\C(=O)OC[C@H]1COC(=O)[C@H]1O |
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InChI Identifier | InChI=1S/C11H14O6/c1-6-8(17-6)2-3-9(12)15-4-7-5-16-11(14)10(7)13/h2-3,6-8,10,13H,4-5H2,1H3/b3-2+/t6-,7-,8+,10-/m0/s1 |
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InChI Key | MDZROSJVVHMKCB-VHSKBXSJSA-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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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 | - Schiewe HJ, Zeeck A: Cineromycins, gamma-butyrolactones and ansamycins by analysis of the secondary metabolite pattern created by a single strain of Streptomyces. J Antibiot (Tokyo). 1999 Jul;52(7):635-42. doi: 10.7164/antibiotics.52.635. [PubMed:10513843 ]
- Jing W, Zhang X, Zhou H, Wang Y, Yang M, Long L, Gao H: Naturally occurring cassane diterpenoids (CAs) of Caesalpinia: A systematic review of its biosynthesis, chemistry and pharmacology. Fitoterapia. 2019 Apr;134:226-249. doi: 10.1016/j.fitote.2019.02.023. Epub 2019 Feb 27. [PubMed:30825578 ]
- Awakawa T, Fujioka T, Zhang L, Hoshino S, Hu Z, Hashimoto J, Kozone I, Ikeda H, Shin-Ya K, Liu W, Abe I: Reprogramming of the antimycin NRPS-PKS assembly lines inspired by gene evolution. Nat Commun. 2018 Aug 30;9(1):3534. doi: 10.1038/s41467-018-05877-z. [PubMed:30166552 ]
- Chen CS, Yu YP, Hsu CH, Zou W, Fang JM, Wu SH: Evaluation of the regioselective delactonization of tri-sialic acid lactone by in-solution molecular dynamics simulation. Carbohydr Res. 2012 Jun 1;354:87-93. doi: 10.1016/j.carres.2012.02.022. Epub 2012 Mar 3. [PubMed:22572126 ]
- Ueki T, Kinoshita T: Stereoselective synthesis and structure of butalactin and lactone II isolated from Streptomyces species. Org Biomol Chem. 2004 Oct 7;2(19):2777-85. doi: 10.1039/B407820A. Epub 2004 Aug 23. [PubMed:15455149 ]
- Ueki T, Morimoto Y, Kinoshita T: Synthesis and absolute configuration of lactone II isolated from Streptomyces sp. Go 40/10. Chem Commun (Camb). 2001 Sep 21;(18):1820-1. doi: 10.1039/b104920h. [PubMed:12240331 ]
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