Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 11:32:28 UTC |
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Updated at | 2022-09-12 11:32:28 UTC |
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NP-MRD ID | NP0328239 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (3s,6s,9s,21as)-1,10-dihydroxy-16-(2-hydroxypropyl)-6-isopropyl-5,8,9-trimethyl-3-(sec-butyl)-3h,6h,9h,12h,13h,16h,19h,20h,21h,21ah-pyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-4,7,14,17-tetrone |
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Description | Destruxin F belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. It was first documented in 2007 (PMID: 18820723). Based on a literature review a significant number of articles have been published on Destruxin F (PMID: 33058930) (PMID: 36130844) (PMID: 36130843) (PMID: 28280843). |
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Structure | CCC(C)[C@@H]1N=C(O)[C@@H]2CCCN2C(=O)C(CC(C)O)OC(=O)CCN=C(O)[C@H](C)N(C)C(=O)[C@H](C(C)C)N(C)C1=O InChI=1S/C29H49N5O8/c1-9-17(4)23-28(40)33(8)24(16(2)3)29(41)32(7)19(6)25(37)30-13-12-22(36)42-21(15-18(5)35)27(39)34-14-10-11-20(34)26(38)31-23/h16-21,23-24,35H,9-15H2,1-8H3,(H,30,37)(H,31,38)/t17?,18?,19-,20-,21?,23-,24-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C29H49N5O8 |
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Average Mass | 595.7380 Da |
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Monoisotopic Mass | 595.35811 Da |
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IUPAC Name | (3S,6S,9S,21aS)-3-(butan-2-yl)-1,10-dihydroxy-16-(2-hydroxypropyl)-5,8,9-trimethyl-6-(propan-2-yl)-3H,4H,5H,6H,7H,8H,9H,12H,13H,14H,16H,17H,19H,20H,21H,21aH-pyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-4,7,14,17-tetrone |
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Traditional Name | (3S,6S,9S,21aS)-1,10-dihydroxy-16-(2-hydroxypropyl)-6-isopropyl-5,8,9-trimethyl-3-(sec-butyl)-3H,6H,9H,12H,13H,16H,19H,20H,21H,21aH-pyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-4,7,14,17-tetrone |
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CAS Registry Number | Not Available |
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SMILES | CCC(C)[C@@H]1N=C(O)[C@@H]2CCCN2C(=O)C(CC(C)O)OC(=O)CCN=C(O)[C@H](C)N(C)C(=O)[C@H](C(C)C)N(C)C1=O |
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InChI Identifier | InChI=1S/C29H49N5O8/c1-9-17(4)23-28(40)33(8)24(16(2)3)29(41)32(7)19(6)25(37)30-13-12-22(36)42-21(15-18(5)35)27(39)34-14-10-11-20(34)26(38)31-23/h16-21,23-24,35H,9-15H2,1-8H3,(H,30,37)(H,31,38)/t17?,18?,19-,20-,21?,23-,24-/m0/s1 |
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InChI Key | UOFIHDFDXCKQGS-CZYRZQCKSA-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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Peptidomimetics |
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Sub Class | Depsipeptides |
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Direct Parent | Cyclic depsipeptides |
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Alternative Parents | |
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Substituents | - Cyclic depsipeptide
- Macrolide lactam
- Macrolactam
- Macrolide
- Alpha-amino acid or derivatives
- Tertiary carboxylic acid amide
- Pyrrolidine
- Carboxamide group
- Carboxylic acid ester
- Lactam
- Lactone
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxylic acid derivative
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Alcohol
- Organic nitrogen compound
- Carbonyl group
- Organooxygen compound
- Organic oxygen compound
- Organonitrogen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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 | - Boot CM, Amagata T, Tenney K, Compton JE, Pietraszkiewicz H, Valeriote FA, Crews P: Four Classes of Structurally Unusual Peptides from Two Marine-Derived Fungi: Structures and Bioactivities. Tetrahedron. 2007 Sep 24;63(39):9903-9914. doi: 10.1016/j.tet.2007.06.034. [PubMed:18820723 ]
- Qasim M, Islam SU, Islam W, Noman A, Khan KA, Hafeez M, Hussain D, Dash CK, Bamisile BS, Akutse KS, Rizwan M, Nisar MS, Jan S, Wang L: Characterization of mycotoxins from entomopathogenic fungi (Cordyceps fumosorosea) and their toxic effects to the development of asian citrus psyllid reared on healthy and diseased citrus plants. Toxicon. 2020 Dec;188:39-47. doi: 10.1016/j.toxicon.2020.10.012. Epub 2020 Oct 12. [PubMed:33058930 ]
- Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
- Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
- Arroyo-Manzanares N, Diana Di Mavungu J, Garrido-Jurado I, Arce L, Vanhaecke L, Quesada-Moraga E, De Saeger S: Analytical strategy for determination of known and unknown destruxins using hybrid quadrupole-Orbitrap high-resolution mass spectrometry. Anal Bioanal Chem. 2017 May;409(13):3347-3357. doi: 10.1007/s00216-017-0276-z. Epub 2017 Mar 9. [PubMed:28280843 ]
- LOTUS database [Link]
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