| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-02 22:04:28 UTC |
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| Updated at | 2022-09-02 22:04:28 UTC |
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| NP-MRD ID | NP0163434 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | bassianolide |
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| Description | Bassianolide, also known as BASS, 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. Bassianolide 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. bassianolide was first documented in 2018 (PMID: 30029532). Based on a literature review a significant number of articles have been published on bassianolide (PMID: 33058930) (PMID: 34512581) (PMID: 33451141) (PMID: 33166889) (PMID: 33053646) (PMID: 31715183). |
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| Structure | CC(C)C[C@@H]1N(C)C(=O)[C@H](OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C)C(C)C InChI=1S/C48H84N4O12/c1-25(2)21-33-45(57)61-38(30(11)12)42(54)50(18)35(23-27(5)6)47(59)63-40(32(15)16)44(56)52(20)36(24-28(7)8)48(60)64-39(31(13)14)43(55)51(19)34(22-26(3)4)46(58)62-37(29(9)10)41(53)49(33)17/h25-40H,21-24H2,1-20H3/t33-,34-,35-,36-,37+,38+,39+,40+/m0/s1 |
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| Synonyms | | Value | Source |
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| (-)-Bassianolide | ChEBI | | BASS | ChEBI |
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| Chemical Formula | C48H84N4O12 |
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| Average Mass | 909.2160 Da |
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| Monoisotopic Mass | 908.60857 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 | CC(C)C[C@@H]1N(C)C(=O)[C@H](OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C)C(C)C |
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| InChI Identifier | InChI=1S/C48H84N4O12/c1-25(2)21-33-45(57)61-38(30(11)12)42(54)50(18)35(23-27(5)6)47(59)63-40(32(15)16)44(56)52(20)36(24-28(7)8)48(60)64-39(31(13)14)43(55)51(19)34(22-26(3)4)46(58)62-37(29(9)10)41(53)49(33)17/h25-40H,21-24H2,1-20H3/t33-,34-,35-,36-,37+,38+,39+,40+/m0/s1 |
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| InChI Key | QVZZPLDJERFENQ-NKTUOASPSA-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
- Tetracarboxylic acid or derivatives
- Macrolide
- Macrolactam
- Alpha-amino acid ester
- Alpha-amino acid or derivatives
- Tertiary carboxylic acid amide
- Lactone
- Lactam
- Carboxylic acid ester
- Carboxamide group
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- 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 | - 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 ]
- D'Amato A, Della Sala G, Izzo I, Costabile C, Masuda Y, De Riccardis F: Cyclic Octamer Peptoids: Simplified Isosters of Bioactive Fungal Cyclodepsipeptides. Molecules. 2018 Jul 19;23(7). pii: molecules23071779. doi: 10.3390/molecules23071779. [PubMed:30029532 ]
- Wang H, Peng H, Li W, Cheng P, Gong M: The Toxins of Beauveria bassiana and the Strategies to Improve Their Virulence to Insects. Front Microbiol. 2021 Aug 26;12:705343. doi: 10.3389/fmicb.2021.705343. eCollection 2021. [PubMed:34512581 ]
- Blaszczyk L, Waskiewicz A, Gromadzka K, Mikolajczak K, Chelkowski J: Sarocladium and Lecanicillium Associated with Maize Seeds and Their Potential to Form Selected Secondary Metabolites. Biomolecules. 2021 Jan 13;11(1):98. doi: 10.3390/biom11010098. [PubMed:33451141 ]
- Li Y, He N, Luo M, Hong B, Xie Y: Application of untargeted tandem mass spectrometry with molecular networking for detection of enniatins and beauvericins from complex samples. J Chromatogr A. 2020 Dec 20;1634:461626. doi: 10.1016/j.chroma.2020.461626. Epub 2020 Oct 22. [PubMed:33166889 ]
- Baldiviezo LV, Pedrini N, Santana M, Mannino MC, Nieva LB, Gentile A, Cardozo RM: Isolation of Beauveria bassiana from the Chagas Disease Vector Triatoma infestans in the Gran Chaco Region of Argentina: Assessment of Gene Expression during Host-Pathogen Interaction. J Fungi (Basel). 2020 Oct 12;6(4):219. doi: 10.3390/jof6040219. [PubMed:33053646 ]
- Cheong PCH, Glare TR, Rostas M, Haines S, Brookes JJ, Ford S: Lack of involvement of chitinase in direct toxicity of Beauveria bassiana cultures to the aphid Myzus persicae. J Invertebr Pathol. 2020 Jan;169:107276. doi: 10.1016/j.jip.2019.107276. Epub 2019 Nov 9. [PubMed:31715183 ]
- Xu F, Butler R, May K, Rexhepaj M, Yu D, Zi J, Chen Y, Liang Y, Zeng J, Hevel J, Zhan J: Modified substrate specificity of a methyltransferase domain by protein insertion into an adenylation domain of the bassianolide synthetase. J Biol Eng. 2019 Jul 31;13:65. doi: 10.1186/s13036-019-0195-y. eCollection 2019. [PubMed:31388353 ]
- Keppanan R, Sivaperumal S, Hussain M, Dash CK, Bamisile BS, Qasim M, Wang L: Corrigendum to "Investigation and molecular docking studies of Bassianolide from Lecanicillium lecanii against Plutella xylostella (Lepidoptera: Plutellidae)" [Comp. Biochem. Physiol. C 206-207 (2018) 65-72]. Comp Biochem Physiol C Toxicol Pharmacol. 2018 Nov;213:62-63. doi: 10.1016/j.cbpc.2018.05.011. Epub 2018 Jun 22. [PubMed:29909016 ]
- LOTUS database [Link]
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