Record Information |
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Version | 1.0 |
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Created at | 2022-09-03 23:06:21 UTC |
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Updated at | 2022-09-03 23:06:21 UTC |
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NP-MRD ID | NP0184071 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 3-[(3s,6s,9s,16r,21as)-3-[(2s)-butan-2-yl]-1,10-dihydroxy-6-isopropyl-5,8,9-trimethyl-4,7,14,17-tetraoxo-3h,6h,9h,12h,13h,16h,19h,20h,21h,21ah-pyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecan-16-yl]-2-methylpropanoic acid |
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Description | Destruxin D 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 2017 (PMID: 28280843). Based on a literature review a significant number of articles have been published on Destruxin D (PMID: 33058930) (PMID: 35696114) (PMID: 33439652) (PMID: 33301677). |
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Structure | CC[C@H](C)[C@@H]1N=C(O)[C@@H]2CCCN2C(=O)[C@@H](CC(C)C(O)=O)OC(=O)CCN=C(O)[C@H](C)N(C)C(=O)[C@H](C(C)C)N(C)C1=O InChI=1S/C30H49N5O9/c1-9-17(4)23-28(40)34(8)24(16(2)3)29(41)33(7)19(6)25(37)31-13-12-22(36)44-21(15-18(5)30(42)43)27(39)35-14-10-11-20(35)26(38)32-23/h16-21,23-24H,9-15H2,1-8H3,(H,31,37)(H,32,38)(H,42,43)/t17-,18?,19-,20-,21+,23-,24-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C30H49N5O9 |
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Average Mass | 623.7480 Da |
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Monoisotopic Mass | 623.35303 Da |
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IUPAC Name | 3-[(3S,6S,9S,16R,21aS)-3-[(2S)-butan-2-yl]-1,10-dihydroxy-5,8,9-trimethyl-4,7,14,17-tetraoxo-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-pentaazacyclononadecan-16-yl]-2-methylpropanoic acid |
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Traditional Name | 3-[(3S,6S,9S,16R,21aS)-3-[(2S)-butan-2-yl]-1,10-dihydroxy-6-isopropyl-5,8,9-trimethyl-4,7,14,17-tetraoxo-3H,6H,9H,12H,13H,16H,19H,20H,21H,21aH-pyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecan-16-yl]-2-methylpropanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC[C@H](C)[C@@H]1N=C(O)[C@@H]2CCCN2C(=O)[C@@H](CC(C)C(O)=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/C30H49N5O9/c1-9-17(4)23-28(40)34(8)24(16(2)3)29(41)33(7)19(6)25(37)31-13-12-22(36)44-21(15-18(5)30(42)43)27(39)35-14-10-11-20(35)26(38)32-23/h16-21,23-24H,9-15H2,1-8H3,(H,31,37)(H,32,38)(H,42,43)/t17-,18?,19-,20-,21+,23-,24-/m0/s1 |
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InChI Key | WTVZRLMVNARECX-ATPFRWRASA-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
- Alpha-amino acid or derivatives
- Dicarboxylic acid or derivatives
- Tertiary carboxylic acid amide
- Pyrrolidine
- Secondary carboxylic acid amide
- Lactone
- Lactam
- Carboxylic acid ester
- Carboxamide group
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- 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 | - 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 ]
- 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 ]
- Hsiao G, Wang SW, Chiang YR, Chi WC, Kuo YH, Phong DA, Chen CY, Lee TH: Anti-inflammatory effects of peptides from a marine algicolous fungus Acremonium sp. NTU492 in BV-2 microglial cells. J Food Drug Anal. 2020 Jun 15;28(2):283-291. doi: 10.38212/2224-6614.1062. [PubMed:35696114 ]
- Zhou T, Katsuragawa M, Xing T, Fukaya K, Okuda T, Tokiwa T, Tashiro E, Imoto M, Oku N, Urabe D, Igarashi Y: Cyclopeptides from the Mushroom Pathogen Fungus Cladobotryum varium. J Nat Prod. 2021 Feb 26;84(2):327-338. doi: 10.1021/acs.jnatprod.0c00980. Epub 2021 Jan 13. [PubMed:33439652 ]
- Liu Z, Sun Y, Tang M, Sun P, Wang A, Hao Y, Wang Y, Pei Y: Trichodestruxins A-D: Cytotoxic Cyclodepsipeptides from the Endophytic Fungus Trichoderma harzianum. J Nat Prod. 2020 Dec 24;83(12):3635-3641. doi: 10.1021/acs.jnatprod.0c00808. Epub 2020 Dec 10. [PubMed:33301677 ]
- LOTUS database [Link]
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