Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:54:47 UTC |
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Updated at | 2021-11-26 17:46:20 UTC |
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NP-MRD ID | NP0044182 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Macrosphelide G |
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Description | Macrosphelide G belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Macrosphelide G is found in Periconia byssoides. It was first documented in 2003 (PMID: 12666244). Based on a literature review a significant number of articles have been published on Macrosphelide G (PMID: 34756847) (PMID: 34758548) (PMID: 34758547) (PMID: 34758546). |
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Structure | C[C@H]1C\C=C/C(=O)O[C@@H](C)[C@H](O)\C=C/C(=O)O[C@H](C)CC(=O)O1 InChI=1S/C16H22O7/c1-10-5-4-6-14(18)23-12(3)13(17)7-8-15(19)22-11(2)9-16(20)21-10/h4,6-8,10-13,17H,5,9H2,1-3H3/b6-4-,8-7-/t10-,11+,12-,13+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C16H22O7 |
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Average Mass | 326.3450 Da |
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Monoisotopic Mass | 326.13655 Da |
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IUPAC Name | (4R,7Z,9R,10S,13Z,16S)-9-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione |
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Traditional Name | (4R,7Z,9R,10S,13Z,16S)-9-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione |
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CAS Registry Number | Not Available |
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SMILES | C[C@H]1C\C=C/C(=O)O[C@@H](C)[C@H](O)\C=C/C(=O)O[C@H](C)CC(=O)O1 |
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InChI Identifier | InChI=1S/C16H22O7/c1-10-5-4-6-14(18)23-12(3)13(17)7-8-15(19)22-11(2)9-16(20)21-10/h4,6-8,10-13,17H,5,9H2,1-3H3/b6-4-,8-7-/t10-,11+,12-,13+/m0/s1 |
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InChI Key | QTVMZKJQTJNPJL-DZQDPMDGSA-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, 50 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Chloroform-d, 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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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Macrolides and analogues |
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Sub Class | Not Available |
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Direct Parent | Macrolides and analogues |
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Alternative Parents | |
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Substituents | - Macrolide
- Tricarboxylic acid or derivatives
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 | - McDonagh MS, Wagner J, Ahmed AY, Morasco B, Kansagara D, Chou R: Living Systematic Review on Cannabis and Other Plant-Based Treatments for Chronic Pain - Quarterly Progress Report/Addendum: September 2021. 2020 Dec. [PubMed:34756847 ]
- Zhang WB, Yang QB, Wu SF, Lu SH, Cheng M, Sheng Y, Zhang QC, Yang LF, Yu L, Yan SX: [Application of diffusion-weighted magnetic resonance imaging in evaluating the efficacy of radiotherapy and chemotherapy for esophageal cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3427-3430. doi: 10.3760/cma.j.cn112137-20210709-01544. [PubMed:34758548 ]
- Sun Y, Wang DM, Yu H, Liu C, Ji TY, Wang S, Wu Y, Liu XY, Jiang YW, Cai LX, Liu QZ: [The screening of potential biological markers of seizure onset zone in focal cortical dysplasia based on bioinformatics analysis]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3422-3426. doi: 10.3760/cma.j.cn112137-20210331-00779. [PubMed:34758547 ]
- Dong HH, Cai YS, Liang XN, Miao JB, Chen QS, Gao YD, Li H: [Analysis of incidence and risk factors for postoperative venous thromboembolism in patients with stage a non-small-cell lung cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3417-3421. doi: 10.3760/cma.j.cn112137-20210418-00929. [PubMed:34758546 ]
- Akita H, Nakamura H, Ono M: Total synthesis of (+)-macrosphelides A, C, E, F, and G based on enzymatic function. Chirality. 2003 May 5;15(4):352-9. doi: 10.1002/chir.10203. [PubMed:12666244 ]
- Takeshi Yamada, Masashi Iritani, Mitsunobu Doi, Katsuhiko Minoura, Tadayoshi Itob and Atsushi Numata (2001). Absolute stereostructures of cell-adhesion inhibitors, macrosphelides C, E–G and I, produced by a Periconia species separated from an Aplysia sea hare. Journal of the Chemical Society Perkin Transactions 1, 2001, 1(22):3046-3053. DOI:10.1039/b104337b. Journal of the Chemical Society Perkin Transactions 1.
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