A QSTR-based expert system to predict sweetness of molecules

Frontiers in Chemistry

Volumn 5, Issue JUL, 2017, Pages

  Rojas, Cristian ^a,b   Todeschini, Roberto ^c   Ballabio, Davide ^c   Mauri, Andrea ^d   Consonni, Viviana ^c   Tripaldi, Piercosimo ^b   Grisoni, Francesca ^c  

^a INSTITUTO DE INVESTIGACIONES FISICOQUÍMICAS TEÓRICAS Y APLICADAS INIFTA   (Argentina)

^b UNIVERSIDAD DEL AZUAY   (Ecuador)

^c UNIVERSITY OF MILANO BICOCCA   (Italy)

^d Kode srl   (Italy)

Author keywords

Classification; Expert system; Molecular descriptors; QSAR; Sweetness

Indexed keywords

EID: 85026784871     PISSN: None     EISSN: 22962646     Source Type: Journal    
DOI: 10.3389/fchem.2017.00053     Document Type: Article

References (58)

1. Balaban, A. T., and Balaban, T.-S. (1991). New vertex invariants and topological indices of chemical graphs based on information on distances. J. Math. Chem. 8, 383-397. doi: 10.1007/BF01166951
2. Ballabio, D. (2015). A MATLAB toolbox for Principal Component Analysis and unsupervised exploration of data structure. Chemom. Intell. Lab. Syst. 149, 1-9. doi: 10.1016/j.chemolab.2015.10.003
3. Ballabio, D., and Consonni, V. (2013). Classification tools in chemistry. Part 1: linear models. PLS-DA. Anal. Methods 5, 3790-3798. doi: 10.1039/c3ay40582f
4. Ballabio, D., Consonni, V., Mauri, A., Claeys-Bruno, M., Sergent, M., and Todeschini, R. (2014). A novel variable reduction method adapted from space-filling designs. Chemom. Intell. Lab. Syst. 136, 147-154. doi: 10.1016/j.chemolab.2014.05.010
5. Bassoli, A., Laureati, M., Borgonovo, G., Morini, G., Servant, G., and Pagliarini, E. (2008). Isovanillic sweeteners: sensory evaluation and in vitro assays with human sweet taste receptor. Chemosens. Percept. 1, 174-183. doi: 10.1007/s12078-008-9027-z
6. Baurin, N., Mozziconacci, J.-C., Arnoult, E., Chavatte, P., Marot, C., and Morin-Allory, L. (2004). 2D QSAR consensus prediction for high-throughput virtual screening. An application to COX-2 inhibition modeling and screening of the NCI database. J. Chem. Inform. Comput. Sci. 44, 276-285. doi: 10.1021/ci0341565
7. Berthold, M., Cebron, N., Dill, F., Gabriel, T., Kötter, T., Meinl, T., et al. (2008). "KNIME: the konstanz information miner," in Data Analysis, Machine Learning and Applications, eds C. Preisach, H. Burkhardt, L. Schmidt-Thieme, and R. Decker (Berlin; Heidelberg: Springer), 319-326
8. Birch, G. G., Karim, R., and Lopez, A. (1994). Novel aspects of structure-activity relationships in sweet taste chemoreception. Food Qual. Prefer. 5, 87-93. doi: 10.1016/0950-3293(94)90012-4
9. Carhart, R. E., Smith, D. H., and Venkataraghavan, R. (1985). Atom pairs as molecular features in structure-activity studies: definition and applications. J. Chem. Inform. Comput. Sci. 25, 64-73. doi: 10.1021/ci00046a002
10. Chéron, J.-B., Casciuc, I., Golebiowski, J., Antonczak, S., and Fiorucci, S. (2017). Sweetness prediction of natural compounds. Food Chem. 221, 1421-1425. doi: 10.1016/j.foodchem.2016.10.145
11. Damodaran, S., Parkin, K. L., and Fennema, O. R. (2008). Fennema's Food Chemistry. Boca Raton, FL; CRC Press
12. Drew, M. G. B., Wilden, G. R. H., Spillane, W. J., Walsh, R. M., Ryder, C. A., and Simmie, J. M. (1998). Quantitative structure-activity relationship studies of sulfamates RNHSO3Na: distinction between sweet, sweet-bitter, and bitter molecules. J. Agric. Food Chem. 46, 3016-3026. doi: 10.1021/jf980095c
13. Ghose, A. K., Viswanadhan, V. N., and Wendoloski, J. J. (1998). Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: an analysis of ALOGP and CLOGP methods. J. Phys. Chem. A 102, 3762-3772. doi: 10.1021/jp980230o
14. Iwamura, H. (1980). Structure-taste relationship of perillartine and nitro-and cyanoaniline derivatives. J. Med. Chem. 23, 308-312. doi: 10.1021/jm00177a020
15. Jaccard, P. (1912). The distribution of the flora in the alpine zone. New Phytol. 11, 37-50. doi: 10.1111/j.1469-8137.1912.tb05611.x
16. Kelly, D. P., Spillane, W. J., and Newell, J. (2005). Development of structure-taste relationships for monosubstituted phenylsulfamate sweeteners using classification and regression tree (CART) Analysis. J. Agric. Food Chem. 53, 6750-6758. doi: 10.1021/jf0507137
17. Kier, L. B. (1980). Molecular structure influencing either a sweet or bitter taste among aldoximes. J. Pharm. Sci. 69, 416-419. doi: 10.1002/jps.2600690414
18. Kode Srl,. P. (2016). Dragon (Software for Molecular Descriptor Calculation) Version 7. Available online at: https://chm.kode-solutions.net
19. Krakowska, B., Custers, D., Deconinck, E., and Daszykowski, M. (2016). The Monte Carlo validation framework for the discriminant partial least squares model extended with variable selection methods applied to authenticity studies of Viagra[registered sign] based on chromatographic impurity profiles. Analyst 141, 1060-1070. doi: 10.1039/C5AN01656H
20. Kruskal, J. B. (1964). Multidimensional scaling by optimizing goodness of fit to a nonmetric hypothesis. Psychometrika 29, 1-27. doi: 10.1007/BF02289565
21. Leardi, R., and González, A. L. (1998). Genetic algorithms applied to feature selection in PLS regression: how and when to use them. Chemom. Intell. Lab. Syst. 41, 195-207. doi: 10.1016/S0169-7439(98)00051-3
22. Li, X., Staszewski, L., Xu, H., Durick, K., Zoller, M., and Adler, E. (2002). Human receptors for sweet and umami taste. Proc. Natl. Acad. Sci. U.S.A. 99, 4692-4696. doi: 10.1073/pnas.072090199
23. Mauri, A., Consonni, V., and Todeschini, R. (2016). "Molecular descriptors," in Handbook of Computational Chemistry, ed J. Leszczynski (Dordrecht: Springer), 1-29
24. Miyashita, Y., Takahashi, Y., Takayama, C., Ohkubo, T., Funatsu, K., and Sasaki, S.-I. (1986a). Computer-assisted structure/taste studies on sulfamates by pattern recognition methods. Anal. Chim. Acta 184, 143-149. doi: 10.1016/S0003-2670(00)86477-6
25. Miyashita, Y., Takahashi, Y., Takayama, C., Sumi, K., Nakatsuka, K., Ohkubo, T., et al. (1986b). Structure-taste correlation of L-aspartyl dipeptides using the SIMCA method. J. Med. Chem. 29, 906-912. doi: 10.1021/jm00156a006
26. Moran, P. A. (1950). Notes on continuous stochastic phenomena. Biometrika 37, 17-23. doi: 10.1093/biomet/37.1-2.17
27. Morini, G., Bassoli, A., and Borgonovo, G. (2011). Molecular modelling and models in the study of sweet and umami taste receptors. A review. Flavour Fragr. J. 26, 254-259. doi: 10.1002/ffj.2054
28. OECD (2007). Guidance Document on the Validation of (Quantitative) Structure-Activity Relationship [(Q)SAR] Models. Paris: OECD Publishing
29. O'Boyle, N. M., Banck, M., James, C. A., Morley, C., Vandermeersch, T., and Hutchison, G. R. (2011). Open babel: an open chemical toolbox. J. Cheminform. 3, 1-14. doi: 10.1186/1758-2946-3-33
30. Ojha, P. K., and Roy, K. (2017). Development of a robust and validated 2D-QSPR model for sweetness potency of diverse functional organic molecules. Food Chem. Toxicol. S0278-S6915, 30139-301344. doi: 10.1016/j.fct.2017.03.043
31. Okuyama, T., Miyashita, Y., Kanaya, S., Katsumi, H., Sasaki, S.-I., and Randic, M. (1988). Computer assisted structure-taste studies on sulfamates by pattern recognition method using graph theoretical invariants. J. Comput. Chem. 9, 636-646. doi: 10.1002/jcc.540090609
32. Pearlman, R. S. (1998). "3D molecular structures: generation and use in 3D searching," in 3D QSAR in Drug Design. Theory and Applications, ed H. Kubinyi (Springer Science and Business Media), 41-79
33. Randic, M. (1997). On characterization of cyclic structures. J. Chem. Inform. Model. 37, 1063-1071. doi: 10.1021/ci9702407
34. Renner, S., Fechner, U., and Schneider, G. (2006). "Alignment-free pharmacophore patterns-A correlation-vector approach," in Pharmacophores and Pharmacophore Searches, eds T. Langer and R. D. Hoffmann (Weinheim: John Wiley & Sons), 395
35. Rogers, D., and Hahn, M. (2010). Extended-connectivity fingerprints. J. Chem. Inform. Model. 50, 742-754. doi: 10.1021/ci100050t
36. Rojas, C., Ballabio, D., Consonni, V., Tripaldi, P., Mauri, A., and Todeschini, R. (2016a). Quantitative structure-activity relationships to predict sweet and non-sweet tastes. Theor. Chem. Acc. 135, 1-13. doi: 10.1007/s00214-016-1812-1
37. Rojas, C., Duchowicz, P. R., Pis Diez, R., and Tripaldi, P. (2016c). "Applications of quantitative structure-relative sweetness relationships in food chemistry," in Chemometrics Applications and Research: QSAR in Medicinal Chemistry, eds A. G. Mercader, R. P. Duchowicz, and P. M. Sivakumar (Waretown, NJ: Apple Academic Press), 317-339
38. Rojas, C., Tripaldi, P., and Duchowicz, P. R. (2016b). A new QSPR study on relative sweetness. Int. J. Quant. Struct. Prop. Relatsh. 1, 76-90. doi: 10.4018/ijqspr.2016010104
39. Shamil, S., Birch, G., Mathlouthi, M., and Clifford, M. (1987). Apparent molar volumes and tastes of molecules with more than one sapophore. Chem. Senses 12, 397-409. doi: 10.1093/chemse/12.2.397
40. Spillane, W. J., and McGlinchey, G. (1981). Structure-activity studies on sulfamate sweeteners II: semiquantitative structure-taste relationship for sulfamate (RNHSO3-) sweeteners-the role of R. J. Pharm. Sci. 70, 933-935. doi: 10.1002/jps.2600700826
41. Spillane, W. J., and Sheahan, M. (1991). Structure-taste relationships for sulfamate sweeteners (RNHSO3-). Phosphorus Sulfur Silicon Relat. Elem. 59, 255-258. doi: 10.1080/10426509108045736
42. Spillane, W. J., and Sheahan, M. B. (1989). Semi-quantitative and quantitative structure-taste relationships for carboand hetero-sulphamate (RNHSO3-) sweeteners. J. Chem. Soc. Perkin Trans. 2, 741-746. doi: 10.1039/P29890000741
43. Spillane, W. J., Coyle, C. M., Feeney, B. G., and Thompson, E. F. (2009). Development of structure-taste relationships for thiazolyl-, benzothiazolyl-, and thiadiazolylsulfamates. J. Agric. Food Chem. 57, 5486-5493. doi: 10.1021/jf9002472
44. Spillane, W. J., Feeney, B. G., and Coyle, C. M. (2002). Further studies on the synthesis and tastes of monosubstituted benzenesulfamates. A semi-quantitative structure-taste relationship for the meta-compounds. Food Chem. 79, 15-22. doi: 10.1016/S0308-8146(02)00169-3
45. Spillane, W. J., Kelly, D. P., Curran, P. J., and Feeney, B. G. (2006). Structure-taste relationships for disubstituted phenylsulfamate tastants using classification and regression tree (CART) analysis. J. Agric. Food Chem. 54, 5996-6004. doi: 10.1021/jf0606656
46. Spillane, W. J., Kelly, L. M., Feeney, B. G., Drew, M. G., and Hattotuwagama, C. K. (2003). Synthesis of heterosulfamates. Search for structure-taste relationships. Arkivoc 7, 297-309. doi: 10.3998/ark.5550190.0004.725
47. Spillane, W. J., McGlinchey, G., Muircheartaigh, I. ó., and Benson, G. A. (1983). Structure-activity studies on sulfamate sweetners III: structure-taste relationships for heterosulfamates. J. Pharm. Sci. 72, 852-856. doi: 10.1002/jps.2600720804
48. Spillane, W. J., Ryder, C. A., Curran, P. J., Wall, S. N., Kelly, L. M., Feeney, B. G., et al. (2000). Development of structure-taste relationships for sweet and non-sweet heterosulfamates. J. Chem. Soc. Perkin Trans. 2, 1369-1374. doi: 10.1039/b002482l
49. Spillane, W. J., Sheahan, M. B., and Ryder, C. A. (1993). Synthesis and taste properties of sodium disubstituted phenylsulfamates. Structure-taste relationships for sweet and bitter/sweet sulfamates. Food Chem. 47, 363-369. doi: 10.1016/0308-8146(93)90178-I
50. Spillane, W., and Malaubier, J.-B. (2014). Sulfamic acid and its N-and O-substituted derivatives. Chem. Rev. 114, 2507-2586. doi: 10.1021/cr400230c
51. Takahashi, Y., Abe, H., Miyashita, Y., Tanaka, Y., Hayasaka, H., and Sasaki, S. I. (1984). Discriminative structural analysis using pattern recognition techniques in the structure-taste problem of perillartines. J. Pharm. Sci. 73, 737-741. doi: 10.1002/jps.2600730608
52. Takahashi, Y., Miyashita, Y., Tanaka, Y., Abe, H., and Sasaki, S. (1982). A consideration for structure-taste correlations of perillartines using pattern-recognition techniques. J. Med. Chem. 25, 1245-1248. doi: 10.1021/jm00352a030
53. Todeschini, R., and Consonni, V. (2009). Molecular Descriptors for Chemoinformatics. Weinheim: Wiley-VCH
54. Todeschini, R., Ballabio, D., Cassotti, M., and Consonni, V. (2015). N3 and BNN: two new similarity based classification methods in comparison with other classifiers. J. Chem. Inform. Model. 55, 2365-2374. doi: 10.1021/acs.jcim.5b00326
55. van der Wel, H., van der Heijden, A., and Peer, H. (1987). Sweeteners. Food Rev. Int. 3, 193-268. doi: 10.1080/87559128709540815
56. Walters, D. E. (2006). "Analysing and predicting properties of sweet-tasting compounds," in Optimising Sweet Taste in Foods, ed W. J. Spillane (Boca Raton, FL: CRC Press), 283-291
57. Wold, S., Sjöström, M., and Eriksson, L. (2001). PLS-regression: a basic tool of chemometrics. Chemom. Intell. Lab. Syst. 58, 109-130. doi: 10.1016/S0169-7439(01)00155-1
58. Yuasa, Y., Nagakura, A., and Tsuruta, H. (1994). The sweetness and stereochemistry of L-aspartyl-fenchylaminoalcohol derivatives. Tetrahedron Lett. 35, 6891-6894. doi: 10.1016/0040-4039(94)85033-X