TETRALIN, INDAN AND NITROBENZENE COMPOUND STRUCTURE-MUSK ODOR RELATIONSHIP USING NEURAL NETWORKS
TETRALIN, INDAN AND NITROBENZENE COMPOUND STRUCTURE-MUSK ODOR RELATIONSHIP USING NEURAL NETWORKS
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DOI：
10.1016/0223-5234(96)88285-7
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发表时间：
1995-01-01
影响因子：
6.7
通讯作者：
PEYRAUD, JF
中科院分区：
文献类型：
--
作者：
CHASTRETTE, M;ELAIDI, C;PEYRAUD, JF
采用神经网络方法，对硝基苯类化合物、羰基四氢萘类化合物和羰基茚满类化合物共105个分子进行了结构-麝香气味关系的研究。每个分子由八个变量描述（六个空间位阻描述符和两个电负性描述符，编码共同基础骨架上的六个取代基（苯环在相对于硝基或羰基的Meta位具有叔丁基或伪叔丁基））。气味是由二进制变量编码的。17个分子可以用两种不同的描述编码，因此反向传播神经网络在122个描述上进行了训练。神经网络给出了更好的分类（98.1%）比判别分析（65.7%）。为了测试神经网络方法的可靠性，在111个训练子集的111或110个描述上进行训练，正确分类率为96.4%至98.6%。对于11或12个描述的11个相应的测试子集，对于105个分子获得80%的正确预测率。评价了每个描述符的贡献。结果表明，具有不同结构的分子建立结构-麝香气味关系的可能性，并证实了前面提到的空间位阻的影响，在邻位的官能团与受体通过氢键相互作用。
Structure-musk odor relationships were established by means of a neural network (NN) on a sample of 105 molecules comprising nitrobenzene compounds, carbonyl tetralins and carbonyl indans. Each molecule was described by eight variables (six steric hindrance descriptors and two electronegativity descriptors, coding six substituents on a common underlying skeleton (benzene ring with a tertiobutyl or pseudo-tertiobutyl group in the meta position relative to a nitro or carbonyl group)). Odor was coded by a binary variable. Seventeen molecules could be coded by two different descriptions, and so the back-propagation NN was trained on 122 descriptions. The NN gave a better classification (98.1%) than that obtained by discriminant analysis (65.7%). To test the reliability of the NN approach, training was made on 11 training subsets of 111 or 110 descriptions with a correct classification rate of 96.4 to 98.6%. For the 11 corresponding test subsets of 11 or 12 descriptions a correct prediction rate of 80% was obtained for the 105 molecules. The contribution of each descriptor was evaluated. The results show the possibility of establishing structure-musk odor relationships for molecules with different structures and confirm the previously mentioned effect of steric hindrance in the ortho position of the functional groups interacting with the receptor by hydrogen bonding.