Accurate Structural Elucidation of Samoquasine A and an Unknown Homologue Using a Computation-Based Machine Learning Protocol
The structure of samoquasine A has long been a subject of controversy, which was resolved only upon its successful total synthesis. We examined the structures of the associated compounds using the state-of-the-art SVM-M protocol. The method accurately discriminated all putative structures historical...
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| Published in | The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Vol. 128; no. 24; pp. 4830 - 4837 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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United States
American Chemical Society
20.06.2024
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| Abstract | The structure of samoquasine A has long been a subject of controversy, which was resolved only upon its successful total synthesis. We examined the structures of the associated compounds using the state-of-the-art SVM-M protocol. The method accurately discriminated all putative structures historically attributed to samoquasine A from a pool of 48 isomeric structures, confirming that samoquasine A is indeed identical to perlolidine. Furthermore, by applying the SVM-M protocol to an additional pool of 67 isomeric structures, we successfully assigned a yet unknown natural product, initially misidentified as perlolidine, as a novel oxime, (E)-3H-cyclopenta[c]quinolin-3-one oxime, representing the first reported cyclone oxime-quinoline natural product. |
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| AbstractList | The structure of samoquasine A has long been a subject of controversy, which was resolved only upon its successful total synthesis. We examined the structures of the associated compounds using the state-of-the-art SVM-M protocol. The method accurately discriminated all putative structures historically attributed to samoquasine A from a pool of 48 isomeric structures, confirming that samoquasine A is indeed identical to perlolidine. Furthermore, by applying the SVM-M protocol to an additional pool of 67 isomeric structures, we successfully assigned a yet unknown natural product, initially misidentified as perlolidine, as a novel oxime, (E)-3H-cyclopenta[c]quinolin-3-one oxime, representing the first reported cyclone oxime-quinoline natural product.The structure of samoquasine A has long been a subject of controversy, which was resolved only upon its successful total synthesis. We examined the structures of the associated compounds using the state-of-the-art SVM-M protocol. The method accurately discriminated all putative structures historically attributed to samoquasine A from a pool of 48 isomeric structures, confirming that samoquasine A is indeed identical to perlolidine. Furthermore, by applying the SVM-M protocol to an additional pool of 67 isomeric structures, we successfully assigned a yet unknown natural product, initially misidentified as perlolidine, as a novel oxime, (E)-3H-cyclopenta[c]quinolin-3-one oxime, representing the first reported cyclone oxime-quinoline natural product. The structure of samoquasine A has long been a subject of controversy, which was resolved only upon its successful total synthesis. We examined the structures of the associated compounds using the state-of-the-art SVM-M protocol. The method accurately discriminated all putative structures historically attributed to samoquasine A from a pool of 48 isomeric structures, confirming that samoquasine A is indeed identical to perlolidine. Furthermore, by applying the SVM-M protocol to an additional pool of 67 isomeric structures, we successfully assigned a yet unknown natural product, initially misidentified as perlolidine, as a novel oxime, (E)-3H-cyclopenta[c]quinolin-3-one oxime, representing the first reported cyclone oxime-quinoline natural product. The structure of samoquasine A has long been a subject of controversy, which was resolved only upon its successful total synthesis. We examined the structures of the associated compounds using the state-of-the-art SVM-M protocol. The method accurately discriminated all putative structures historically attributed to samoquasine A from a pool of 48 isomeric structures, confirming that samoquasine A is indeed identical to perlolidine. Furthermore, by applying the SVM-M protocol to an additional pool of 67 isomeric structures, we successfully assigned a yet unknown natural product, initially misidentified as perlolidine, as a novel oxime, ( )-3 -cyclopenta[ ]quinolin-3-one oxime, representing the first reported cyclone oxime-quinoline natural product. |
| Author | Chen, Qiwen Ye, Jianliang Wu, Anan Feng, Jin Xu, Xin |
| AuthorAffiliation | Fujian Provincial Key Laboratory for Theoretical and Computational Chemistry, Departmental of Chemistry, College of Chemistry and Chemical Engineering Collaborative Innovation Center of Chemistry for Energy Materials, Shanghai; Key Laboratory of Molecular Catalysis and Innovative Materials; MOE Key Laboratory of Computational Physical Sciences; Department of Chemistry |
| AuthorAffiliation_xml | – name: Collaborative Innovation Center of Chemistry for Energy Materials, Shanghai; Key Laboratory of Molecular Catalysis and Innovative Materials; MOE Key Laboratory of Computational Physical Sciences; Department of Chemistry – name: Fujian Provincial Key Laboratory for Theoretical and Computational Chemistry, Departmental of Chemistry, College of Chemistry and Chemical Engineering |
| Author_xml | – sequence: 1 givenname: Anan orcidid: 0000-0001-5243-9291 surname: Wu fullname: Wu, Anan email: ananwu@xmu.edu.cn organization: Fujian Provincial Key Laboratory for Theoretical and Computational Chemistry, Departmental of Chemistry, College of Chemistry and Chemical Engineering – sequence: 2 givenname: Qiwen surname: Chen fullname: Chen, Qiwen organization: Fujian Provincial Key Laboratory for Theoretical and Computational Chemistry, Departmental of Chemistry, College of Chemistry and Chemical Engineering – sequence: 3 givenname: Jin surname: Feng fullname: Feng, Jin organization: Fujian Provincial Key Laboratory for Theoretical and Computational Chemistry, Departmental of Chemistry, College of Chemistry and Chemical Engineering – sequence: 4 givenname: Jianliang orcidid: 0000-0003-1488-7311 surname: Ye fullname: Ye, Jianliang email: yejl@xmu.edu.cn organization: Fujian Provincial Key Laboratory for Theoretical and Computational Chemistry, Departmental of Chemistry, College of Chemistry and Chemical Engineering – sequence: 5 givenname: Xin orcidid: 0000-0002-5247-2937 surname: Xu fullname: Xu, Xin email: xxchem@fudan.edu.cn organization: Collaborative Innovation Center of Chemistry for Energy Materials, Shanghai; Key Laboratory of Molecular Catalysis and Innovative Materials; MOE Key Laboratory of Computational Physical Sciences; Department of Chemistry |
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| Title | Accurate Structural Elucidation of Samoquasine A and an Unknown Homologue Using a Computation-Based Machine Learning Protocol |
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