| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-05 11:52:18 UTC |
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| Updated at | 2022-09-05 11:52:18 UTC |
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| NP-MRD ID | NP0213023 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | filipin iii |
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| Description | Filipin III, also known as filimarisin or 14-deoxylagosin, 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. Filipin III 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. filipin iii is found in Streptomyces avermitilis, Streptomyces filipinensis and Streptomyces miharaensis. filipin iii was first documented in 2021 (PMID: 34361779). Based on a literature review a small amount of articles have been published on filipin III (PMID: 35892953) (PMID: 35678098) (PMID: 35204701) (PMID: 34562242). |
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| Structure | CCCCC[C@@H](O)[C@@H]1[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@H](O)\C(C)=C\C=C\C=C\C=C\C=C\[C@H](O)[C@@H](C)OC1=O InChI=1S/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14+/t24-,25+,26-,27+,28-,29+,30+,31-,32+,33+,34-/m1/s1 |
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| Synonyms | | Value | Source |
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| 14-Deoxylagosin | ChEBI | | Filimarisin | ChEBI | | Filipin | ChEBI | | Filipina | ChEBI | | Filipine | ChEBI | | Filipinum | ChEBI | | Filipin IV | MeSH | | Filipin I | MeSH | | Filipin II | MeSH | | Desoxylagosin | MeSH |
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| Chemical Formula | C35H58O11 |
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| Average Mass | 654.8380 Da |
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| Monoisotopic Mass | 654.39791 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 | CCCCC[C@@H](O)[C@@H]1[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@H](O)\C(C)=C\C=C\C=C\C=C\C=C\[C@H](O)[C@@H](C)OC1=O |
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| InChI Identifier | InChI=1S/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14+/t24-,25+,26-,27+,28-,29+,30+,31-,32+,33+,34-/m1/s1 |
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| InChI Key | IMQSIXYSKPIGPD-YQRUMEKGSA-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 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
- Fatty alcohol
- Fatty acyl
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Polyol
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Carbonyl group
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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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 | - Zuniga R, Mancilla D, Rojas T, Vergara F, Gonzalez W, Catalan MA, Zuniga L: A Direct Interaction between Cyclodextrins and TASK Channels Decreases the Leak Current in Cerebellar Granule Neurons. Biology (Basel). 2022 Jul 23;11(8):1097. doi: 10.3390/biology11081097. [PubMed:35892953 ]
- Li L, Liu Y, Liu X, Zheng N, Gu Y, Song Y, Wang X: Regulatory roles of external cholesterol in human airway epithelial mitochondrial function through STARD3 signalling. Clin Transl Med. 2022 Jun;12(6):e902. doi: 10.1002/ctm2.902. [PubMed:35678098 ]
- Pavlik V, Machalova V, Cepa M, Sinova R, Safrankova B, Kulhanek J, Drmota T, Kubala L, Huerta-Angeles G, Velebny V, Nesporova K: Retinoic Acid Grafted to Hyaluronic Acid Activates Retinoid Gene Expression and Removes Cholesterol from Cellular Membranes. Biomolecules. 2022 Jan 25;12(2):200. doi: 10.3390/biom12020200. [PubMed:35204701 ]
- Miyamoto T, Hosoba K, Akutsu SN, Matsuura S: Imaging of the Ciliary Cholesterol Underlying the Sonic Hedgehog Signal Transduction. Methods Mol Biol. 2022;2374:49-57. doi: 10.1007/978-1-0716-1701-4_5. [PubMed:34562242 ]
- Maddila SC, Voshavar C, Arjunan P, Chowath RP, Rachamalla HKR, Balakrishnan B, Balasubramanian P, Banerjee R, Marepally S: Cholesterol Sequestration from Caveolae/Lipid Rafts Enhances Cationic Liposome-Mediated Nucleic Acid Delivery into Endothelial Cells. Molecules. 2021 Jul 30;26(15):4626. doi: 10.3390/molecules26154626. [PubMed:34361779 ]
- LOTUS database [Link]
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