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Volumn 17, Issue 6, 2016, Pages

In Silico prediction of cytochrome P450-drug interaction: QSARs for CYP3a4 and CYP2C9

Author keywords

ADMET; CYP2C9; CYP3A4; Cytochrome P450; In silico; QSAR

Indexed keywords

CYTOCHROME P450 2C9; CYTOCHROME P450 3A4; CYTOCHROME P450 2C9 INHIBITOR; CYTOCHROME P450 3A; CYTOCHROME P450 3A INHIBITOR; PROTEIN BINDING;

EID: 84973527678     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms17060914     Document Type: Article
Times cited : (58)

References (71)
  • 2
    • 0035523337 scopus 로고    scopus 로고
    • Metabolism Profiling, and Cytochrome P450 inhibition & induction in drug discovery
    • [PubMed]
    • Yan, Z.; Caldwell, G.W. Metabolism Profiling, and Cytochrome P450 inhibition & induction in drug discovery. Curr. Top. Med. Chem. 2001, 1, 403-425. [PubMed]
    • (2001) Curr. Top. Med. Chem , vol.1 , pp. 403-425
    • Yan, Z.1    Caldwell, G.W.2
  • 3
    • 80052847569 scopus 로고    scopus 로고
    • Novel advances in cytochrome P450 research
    • [CrossRef] [PubMed]
    • Singh, D.; Kashyap, A.; Pandey, R.V.; Saini, K.S. Novel advances in cytochrome P450 research. Drug Discov. Today 2011, 16, 793-799. [CrossRef] [PubMed]
    • (2011) Drug Discov. Today , vol.16 , pp. 793-799
    • Singh, D.1    Kashyap, A.2    Pandey, R.V.3    Saini, K.S.4
  • 4
    • 84875211310 scopus 로고    scopus 로고
    • Cytochrome P450 enzymes in drug metabolism: Regulation of gene expression, enzyme activities, and impact of genetic variation
    • [CrossRef] [PubMed]
    • Zanger, U.M.; Schwab, M. Cytochrome P450 enzymes in drug metabolism: Regulation of gene expression, enzyme activities, and impact of genetic variation. Pharmacol. Ther. 2013, 138, 103-141. [CrossRef] [PubMed]
    • (2013) Pharmacol. Ther , vol.138 , pp. 103-141
    • Zanger, U.M.1    Schwab, M.2
  • 5
    • 0025688972 scopus 로고
    • Role of cytochromes P450 in drug metabolism and hepatotoxicity
    • Pb, W. Role of cytochromes P450 in drug metabolism and hepatotoxicity. Semin. Liver Dis. 1990, 10, 235-250.
    • (1990) Semin. Liver Dis , vol.10 , pp. 235-250
    • Pb, W.1
  • 6
    • 0028272001 scopus 로고
    • Role of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxins
    • [CrossRef] [PubMed]
    • Gonzalez, F.J.; Gelboin, H.V. Role of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxins. Drug Metab. Rev. 1994, 26, 165-183. [CrossRef] [PubMed]
    • (1994) Drug Metab. Rev , vol.26 , pp. 165-183
    • Gonzalez, F.J.1    Gelboin, H.V.2
  • 7
    • 10444229539 scopus 로고    scopus 로고
    • Role of cytochromes P450 in chemical toxicity and oxidative stress: Studies with CYP2E1
    • [CrossRef] [PubMed]
    • Gonzalez, F.J. Role of cytochromes P450 in chemical toxicity and oxidative stress: Studies with CYP2E1. Mutat. Res. Mol. Mech. Mutagen. 2005, 569, 101-110. [CrossRef] [PubMed]
    • (2005) Mutat. Res. Mol. Mech. Mutagen , vol.569 , pp. 101-110
    • Gonzalez, F.J.1
  • 8
    • 0037204551 scopus 로고    scopus 로고
    • Computer systems for the prediction of xenobiotic metabolism
    • [CrossRef]
    • Langowski, J.; Long, A. Computer systems for the prediction of xenobiotic metabolism. Adv. Drug Deliv. Rev. 2002, 54, 407-415. [CrossRef]
    • (2002) Adv. Drug Deliv. Rev , vol.54 , pp. 407-415
    • Langowski, J.1    Long, A.2
  • 11
    • 53249095707 scopus 로고    scopus 로고
    • Considerations and recent advances in QSAR models for cytochrome P450-mediated drug metabolism prediction
    • [CrossRef] [PubMed]
    • Li, H.; Sun, J.; Fan, X.; Sui, X.; Zhang, L.; Wang, Y.; He, Z. Considerations and recent advances in QSAR models for cytochrome P450-mediated drug metabolism prediction. J. Comput. Aided Mol. Des. 2008, 22, 843-855. [CrossRef] [PubMed]
    • (2008) J. Comput. Aided Mol. Des , vol.22 , pp. 843-855
    • Li, H.1    Sun, J.2    Fan, X.3    Sui, X.4    Zhang, L.5    Wang, Y.6    He, Z.7
  • 12
    • 23844460948 scopus 로고    scopus 로고
    • Prediction of Cytochrome P450 3A4, 2D6, and 2C9 inhibitors and substrates by using support vector machines
    • [CrossRef] [PubMed]
    • Yap, C.W.; Chen, Y.Z. Prediction of Cytochrome P450 3A4, 2D6, and 2C9 inhibitors and substrates by using support vector machines. J. Chem. Inf. Model. 2005, 45, 982-992. [CrossRef] [PubMed]
    • (2005) J. Chem. Inf. Model , vol.45 , pp. 982-992
    • Yap, C.W.1    Chen, Y.Z.2
  • 13
    • 84880983289 scopus 로고    scopus 로고
    • WhichCyp: Prediction of cytochromes P450 inhibition
    • [CrossRef] [PubMed]
    • Rostkowski, M.; Spjuth, O.; Rydberg, P. WhichCyp: Prediction of cytochromes P450 inhibition. Bioinformatics 2013, 29, 2051-2052. [CrossRef] [PubMed]
    • (2013) Bioinformatics , vol.29 , pp. 2051-2052
    • Rostkowski, M.1    Spjuth, O.2    Rydberg, P.3
  • 14
    • 84944104817 scopus 로고    scopus 로고
    • An improved large-scale prediction model of CYP1A2 inhibitors by using combined fragment descriptors
    • [CrossRef]
    • Pan, X.; Chao, L.; Qu, S.; Huang, S.; Yang, L.; Mei, H. An improved large-scale prediction model of CYP1A2 inhibitors by using combined fragment descriptors. RSC Adv. 2015, 5, 84232-84237. [CrossRef]
    • (2015) RSC Adv , vol.5 , pp. 84232-84237
    • Pan, X.1    Chao, L.2    Qu, S.3    Huang, S.4    Yang, L.5    Mei, H.6
  • 15
    • 80054909003 scopus 로고    scopus 로고
    • Predictive models for cytochrome P450 isozymes based on quantitative high throughput screening data
    • [CrossRef] [PubMed]
    • Sun, H.; Veith, H.; Xia, M.; Austin, C.P.; Huang, R. Predictive models for cytochrome P450 isozymes based on quantitative high throughput screening data. J. Chem. Inf. Model. 2011, 51, 2474-2481. [CrossRef] [PubMed]
    • (2011) J. Chem. Inf. Model , vol.51 , pp. 2474-2481
    • Sun, H.1    Veith, H.2    Xia, M.3    Austin, C.P.4    Huang, R.5
  • 16
    • 33846923287 scopus 로고    scopus 로고
    • In silico prediction of cytochrome P450 2D6 and 3A4 inhibition using gaussian kernel weighted k-Nearest neighbor and extended connectivity fingerprints, including structural fragment analysis of inhibitors versus noninhibitors
    • [CrossRef] [PubMed]
    • Jensen, B.F.; Vind, C.; Brockhoff, P.B.; Refsgaard, H.H.F. In silico prediction of cytochrome P450 2D6 and 3A4 inhibition using gaussian kernel weighted k-Nearest neighbor and extended connectivity fingerprints, including structural fragment analysis of inhibitors versus noninhibitors. J. Med. Chem. 2007, 50, 501-511. [CrossRef] [PubMed]
    • (2007) J. Med. Chem , vol.50 , pp. 501-511
    • Jensen, B.F.1    Vind, C.2    Brockhoff, P.B.3    Refsgaard, H.H.F.4
  • 19
    • 84973549663 scopus 로고    scopus 로고
    • (accessed on1 March 2016)
    • NCBI The PubChem Project. Available online: http://pubchem.ncbi.nlm.nih.gov/(accessed on1 March 2016).
    • NCBI the Pubchem Project
  • 21
    • 84973534924 scopus 로고    scopus 로고
    • accessed on 8 June 2016
    • Available online: http://www.talete.mi.it/(accessed on 8 June 2016).
    • (2012)
  • 22
    • 77952772341 scopus 로고    scopus 로고
    • Extended-connectivity fingerprints
    • [CrossRef] [PubMed]
    • Rogers, D.; Hahn, M. Extended-connectivity fingerprints. J. Chem. Inf. Model. 2010, 50, 742-754. [CrossRef] [PubMed]
    • (2010) J. Chem. Inf. Model , vol.50 , pp. 742-754
    • Rogers, D.1    Hahn, M.2
  • 24
    • 84951507118 scopus 로고
    • Genetic algorithms and machine learning
    • [CrossRef]
    • Goldberg, D.E.; Holland, J.H. Genetic algorithms and machine learning. Mach. Learn. 1988, 3, 95-99. [CrossRef]
    • (1988) Mach. Learn , vol.3 , pp. 95-99
    • Goldberg, D.E.1    Holland, J.H.2
  • 25
    • 84897543946 scopus 로고    scopus 로고
    • Reshaped sequential replacement for variable selection in QSPR: Comparison with other reference methods
    • [CrossRef]
    • Grisoni, F.; Cassotti, M.; Todeschini, R. Reshaped sequential replacement for variable selection in QSPR: Comparison with other reference methods. J. Chemom. 2014, 28, 249-259. [CrossRef]
    • (2014) J. Chemom , vol.28 , pp. 249-259
    • Grisoni, F.1    Cassotti, M.2    Todeschini, R.3
  • 27
    • 0001757405 scopus 로고
    • K-Nearest Neighbor Classification Rule (Pattern recognition) applied to nuclear magnetic resonance spectral interpretation
    • [CrossRef]
    • Kowalski, B.R.; Bender, C.F. K-Nearest Neighbor Classification Rule (pattern recognition) applied to nuclear magnetic resonance spectral interpretation. Anal. Chem. 1972, 44, 1405-1411. [CrossRef]
    • (1972) Anal. Chem , vol.44 , pp. 1405-1411
    • Kowalski, B.R.1    Bender, C.F.2
  • 28
    • 84936798684 scopus 로고    scopus 로고
    • N3 and BNN: Two new similarity based classification methods in comparison with other classifiers
    • [CrossRef] [PubMed]
    • Todeschini, R.; Ballabio, D.; Cassotti, M.; Consonni, V. N3 and BNN: Two new similarity based classification methods in comparison with other classifiers. J. Chem. Inf. Model. 2015, 55, 2365-2374. [CrossRef] [PubMed]
    • (2015) J. Chem. Inf. Model , vol.55 , pp. 2365-2374
    • Todeschini, R.1    Ballabio, D.2    Cassotti, M.3    Consonni, V.4
  • 30
    • 85164278893 scopus 로고
    • Partial least squares analysis with cross-validation for the two-class problem: A Monte Carlo study
    • [CrossRef]
    • Ståhle, L.; Wold, S. Partial least squares analysis with cross-validation for the two-class problem: A Monte Carlo study. J. Chemom. 1987, 1, 185-196. [CrossRef]
    • (1987) J. Chemom , vol.1 , pp. 185-196
    • Ståhle, L.1    Wold, S.2
  • 31
    • 84861521242 scopus 로고    scopus 로고
    • Comparison of different approaches to define the applicability domain of QSAR models
    • [CrossRef] [PubMed]
    • Sahigara, F.; Mansouri, K.; Ballabio, D.; Mauri, A.; Consonni, V.; Todeschini, R. Comparison of different approaches to define the applicability domain of QSAR models. Molecules 2012, 17, 4791-4810. [CrossRef] [PubMed]
    • (2012) Molecules , vol.17 , pp. 4791-4810
    • Sahigara, F.1    Mansouri, K.2    Ballabio, D.3    Mauri, A.4    Consonni, V.5    Todeschini, R.6
  • 32
    • 84988471224 scopus 로고    scopus 로고
    • Principal component analysis
    • John Wiley & Sons, Ltd.: Boca Raton, FL, USA
    • Jolliffe, I. Principal component analysis. In Wiley StatsRef: Statistics Reference Online; John Wiley & Sons, Ltd.: Boca Raton, FL, USA, 2014.
    • (2014) Wiley Statsref: Statistics Reference Online
    • Jolliffe, I.1
  • 33
    • 0029865450 scopus 로고    scopus 로고
    • Design of drugs involving the concepts and theories of drug metabolism and pharmacokinetics
    • [CrossRef]
    • Smith, D.A.; Jones, B.C.; Walker, D.K. Design of drugs involving the concepts and theories of drug metabolism and pharmacokinetics. Med. Res. Rev. 1996, 16, 243-266. [CrossRef]
    • (1996) Med. Res. Rev. , vol.16 , pp. 243-266
    • Smith, D.A.1    Jones, B.C.2    Walker, D.K.3
  • 35
    • 36048939609 scopus 로고    scopus 로고
    • Mechanisms of cytochrome P450 substrate oxidation: MiniReview
    • [CrossRef] [PubMed]
    • Guengerich, F.P. Mechanisms of cytochrome P450 substrate oxidation: MiniReview. J. Biochem. Mol. Toxicol. 2007, 21, 163-168. [CrossRef] [PubMed]
    • (2007) J. Biochem. Mol. Toxicol. , vol.21 , pp. 163-168
    • Guengerich, F.P.1
  • 36
    • 0024326020 scopus 로고
    • Oxidation of halogenated compounds by cytochrome P-450, peroxidases, and model metalloporphyrins
    • Guengerich, F.P. Oxidation of halogenated compounds by cytochrome P-450, peroxidases, and model metalloporphyrins. J. Biol. Chem. 1989, 264, 17198-17205.
    • (1989) J. Biol. Chem , vol.264 , pp. 17198-17205
    • Guengerich, F.P.1
  • 37
    • 4644275807 scopus 로고    scopus 로고
    • Mechanism of oxidation reactions catalyzed by cytochrome P450 enzymes
    • [CrossRef] [PubMed]
    • Meunier, B.; Visser, S.P.D. Mechanism of oxidation reactions catalyzed by cytochrome P450 enzymes. Chem. Rev. 2004, 104, 3947-3980. [CrossRef] [PubMed]
    • (2004) Chem. Rev , vol.104 , pp. 3947-3980
    • Meunier, B.1    Visser, S.P.D.2
  • 39
    • 0014220832 scopus 로고
    • Hydroxylation-induced migration: The NIH shift. Recent experiments reveal an unexpected and general result of enzymatic hydroxylation of aromatic compounds
    • [CrossRef] [PubMed]
    • Guroff, G.; Daly, J.W.; Jerina, D.M.; Renson, J.; Witkop, B.; Udenfriend, S. Hydroxylation-induced migration: The NIH shift. Recent experiments reveal an unexpected and general result of enzymatic hydroxylation of aromatic compounds. Science 1967, 157, 1524-1530. [CrossRef] [PubMed]
    • (1967) Science , vol.157 , pp. 1524-1530
    • Guroff, G.1    Daly, J.W.2    Jerina, D.M.3    Renson, J.4    Witkop, B.5    Udenfriend, S.6
  • 40
    • 0011479353 scopus 로고
    • Topological indices based on neighborhood symmetry: Chemical and biological applications
    • Magnuson, V.R.; Harriss, D.K.; Basak, S.C. Topological indices based on neighborhood symmetry: Chemical and biological applications. Chem. Appl. Topol. Graph Theory 1983, 178-191.
    • (1983) Chem. Appl. Topol. Graph Theory , pp. 178-191
    • Magnuson, V.R.1    Harriss, D.K.2    Basak, S.C.3
  • 41
    • 84930650069 scopus 로고    scopus 로고
    • Modeling of interactions between xenobiotics and cytochrome P450 (CYP) enzymes
    • [CrossRef] [PubMed]
    • Raunio, H.; Kuusisto, M.; Juvonen, R.O.; Pentikäinen, O.T. Modeling of interactions between xenobiotics and cytochrome P450 (CYP) enzymes. Front. Pharmacol. 2015, 6. [CrossRef] [PubMed]
    • (2015) Front. Pharmacol , pp. 6
    • Raunio, H.1    Kuusisto, M.2    Juvonen, R.O.3    Pentikäinen, O.T.4
  • 42
    • 44049091290 scopus 로고    scopus 로고
    • Calculation of protein-ligand binding free energy by using a polarizable potential
    • [CrossRef] [PubMed]
    • Jiao, D.; Golubkov, P.A.; Darden, T.A.; Ren, P. Calculation of protein-ligand binding free energy by using a polarizable potential. Proc. Natl. Acad. Sci. USA 2008, 105, 6290-6295. [CrossRef] [PubMed]
    • (2008) Proc. Natl. Acad. Sci. USA , vol.105 , pp. 6290-6295
    • Jiao, D.1    Golubkov, P.A.2    Darden, T.A.3    Ren, P.4
  • 43
    • 0028355745 scopus 로고
    • Electrostatic potential of the acetylcholine binding sites in the nicotinic receptor probed by reactions of binding-site cysteines with charged methanethiosulfonates
    • [CrossRef] [PubMed]
    • Stauffer, D.A.; Karlin, A. Electrostatic potential of the acetylcholine binding sites in the nicotinic receptor probed by reactions of binding-site cysteines with charged methanethiosulfonates. Biochemistry 1994, 33, 6840-6849. [CrossRef] [PubMed]
    • (1994) Biochemistry , vol.33 , pp. 6840-6849
    • Stauffer, D.A.1    Karlin, A.2
  • 44
    • 12344303439 scopus 로고    scopus 로고
    • Performance of Kier-hall E-state descriptors in quantitative structure activity relationship (QSAR) studies of multifunctional molecules
    • [CrossRef] [PubMed]
    • Butina, D. Performance of Kier-hall E-state descriptors in quantitative structure activity relationship (QSAR) studies of multifunctional molecules. Molecules 2004, 9, 1004-1009. [CrossRef] [PubMed]
    • (2004) Molecules , vol.9 , pp. 1004-1009
    • Butina, D.1
  • 46
    • 0034768019 scopus 로고    scopus 로고
    • Phenytoin and fluorouracil interaction
    • [CrossRef] [PubMed]
    • Gilbar, P.J.; Brodribb, T.R. Phenytoin and fluorouracil interaction. Ann. Pharmacother. 2001, 35, 1367-1370. [CrossRef] [PubMed]
    • (2001) Ann. Pharmacother , vol.35 , pp. 1367-1370
    • Gilbar, P.J.1    Brodribb, T.R.2
  • 47
    • 0032844275 scopus 로고    scopus 로고
    • An adverse interaction between warfarin and 5-fluorouracil: A case report and review of the literature
    • [CrossRef] [PubMed]
    • Brown, M.C. An adverse interaction between warfarin and 5-fluorouracil: A case report and review of the literature. Chemotherapy 1999, 45, 392-395. [CrossRef] [PubMed]
    • (1999) Chemotherapy , vol.45 , pp. 392-395
    • Brown, M.C.1
  • 48
    • 0035894174 scopus 로고    scopus 로고
    • The anticancer agent ellipticine on activation by cytochrome P450 forms covalent DNA adducts
    • [CrossRef]
    • Stiborová, M.; Bieler, C.A.; Wiessler, M.; Frei, E. The anticancer agent ellipticine on activation by cytochrome P450 forms covalent DNA adducts. Biochem. Pharmacol. 2001, 62, 1675-1684. [CrossRef]
    • (2001) Biochem. Pharmacol , vol.62 , pp. 1675-1684
    • Stiborová, M.1    Bieler, C.A.2    Wiessler, M.3    Frei, E.4
  • 49
    • 0030772328 scopus 로고    scopus 로고
    • The role of non-P450 enzymes in drug oxidation
    • [CrossRef] [PubMed]
    • Beedham, C. The role of non-P450 enzymes in drug oxidation. Pharm. World Sci. 1997, 19, 255-263. [CrossRef] [PubMed]
    • (1997) Pharm. World Sci , vol.19 , pp. 255-263
    • Beedham, C.1
  • 50
    • 1842728122 scopus 로고    scopus 로고
    • QSPR with TAU indices: Water solubility of diverse functional acyclic compounds
    • Roy, K.; Saha, A. QSPR with TAU indices: Water solubility of diverse functional acyclic compounds. Intern. Electron. J. Mol. Des. 2003, 2, 475-491.
    • (2003) Intern. Electron. J. Mol. Des , vol.2 , pp. 475-491
    • Roy, K.1    Saha, A.2
  • 51
    • 0026597449 scopus 로고
    • Simple method of calculating octanol/water partition coefficient
    • [CrossRef]
    • Moriguchi, I.; Hirono, S.; Liu, Q.; Nakagome, I.; Matsushita, Y. Simple method of calculating octanol/water partition coefficient. Chem. Pharm. Bull. 1992, 40, 127-130. [CrossRef]
    • (1992) Chem. Pharm. Bull , vol.40 , pp. 127-130
    • Moriguchi, I.1    Hirono, S.2    Liu, Q.3    Nakagome, I.4    Matsushita, Y.5
  • 52
    • 2942625954 scopus 로고    scopus 로고
    • Compound lipophilicity for substrate binding to human P450s in drug metabolism
    • [CrossRef]
    • Lewis, D.F.V.; Jacobs, M.N.; Dickins, M. Compound lipophilicity for substrate binding to human P450s in drug metabolism. Drug Discov. Today 2004, 9, 530-537. [CrossRef]
    • (2004) Drug Discov. Today , vol.9 , pp. 530-537
    • Lewis, D.F.V.1    Jacobs, M.N.2    Dickins, M.3
  • 53
    • 0027534457 scopus 로고
    • Quantitative structure-activity relationships of cytochrome P-450
    • [CrossRef] [PubMed]
    • Hansch, C.; Zhang, L. Quantitative structure-activity relationships of cytochrome P-450. Drug Metab. Rev. 1993, 25, 1-48. [CrossRef] [PubMed]
    • (1993) Drug Metab. Rev , vol.25 , pp. 1-48
    • Hansch, C.1    Zhang, L.2
  • 54
    • 0018145146 scopus 로고
    • The role of substrate lipophilicity in determining type 1 microsomal P450 binding characteristics
    • [CrossRef]
    • Al-Gailany, K.A.S.; Houston, J.B.; Bridges, J.W. The role of substrate lipophilicity in determining type 1 microsomal P450 binding characteristics. Biochem. Pharmacol. 1978, 27, 783-788. [CrossRef]
    • (1978) Biochem. Pharmacol , vol.27 , pp. 783-788
    • Al-Gailany, K.A.S.1    Houston, J.B.2    Bridges, J.W.3
  • 55
    • 0029988975 scopus 로고    scopus 로고
    • Quantitative structure activity relationship for the effect of benzoic acids, cinnamic acids and benzaldehydes on Listeria monocytogenes
    • [CrossRef] [PubMed]
    • Ramos-Nino, M.E.; Clifford, M.N.; Adams, M.R. Quantitative structure activity relationship for the effect of benzoic acids, cinnamic acids and benzaldehydes on Listeria monocytogenes. J. Appl. Bacteriol. 1996, 80, 303-310. [CrossRef] [PubMed]
    • (1996) J. Appl. Bacteriol. , vol.80 , pp. 303-310
    • Ramos-Nino, M.E.1    Clifford, M.N.2    Adams, M.R.3
  • 56
    • 46449133537 scopus 로고    scopus 로고
    • New spectral indices for molecule description
    • Consonni, V.; Todeschini, R. New spectral indices for molecule description. MATCH 2008, 1, 2.
    • (2008) MATCH , vol.1 , pp. 2
    • Consonni, V.1    Todeschini, R.2
  • 57
    • 0000960565 scopus 로고
    • The contiguity ratio and statistical mapping
    • [CrossRef]
    • Geary, R.C. The contiguity ratio and statistical mapping. Inc. Stat. 1954, 5, 115-146. [CrossRef]
    • (1954) Inc. Stat , vol.5 , pp. 115-146
    • Geary, R.C.1
  • 58
    • 33845379303 scopus 로고
    • Atom pairs as molecular features in structure-activity studies: Definition and applications
    • [CrossRef]
    • Carhart, R.E.; Smith, D.H.; Venkataraghavan, R. Atom pairs as molecular features in structure-activity studies: Definition and applications. J. Chem. Inf. Comput. Sci. 1985, 25, 64-73. [CrossRef]
    • (1985) J. Chem. Inf. Comput. Sci , vol.25 , pp. 64-73
    • Carhart, R.E.1    Smith, D.H.2    Venkataraghavan, R.3
  • 59
    • 84952923189 scopus 로고    scopus 로고
    • Investigating the mechanisms of bioconcentration through QSAR classification trees
    • [CrossRef] [PubMed]
    • Grisoni, F.; Consonni, V.; Vighi, M.; Villa, S.; Todeschini, R. Investigating the mechanisms of bioconcentration through QSAR classification trees. Environ. Int. 2016, 88, 198-205. [CrossRef] [PubMed]
    • (2016) Environ. Int , vol.88 , pp. 198-205
    • Grisoni, F.1    Consonni, V.2    Vighi, M.3    Villa, S.4    Todeschini, R.5
  • 60
    • 84919837974 scopus 로고    scopus 로고
    • Validation and extension of a similarity-based approach for prediction of acute aquatic toxicity towards Daphnia magna
    • [CrossRef] [PubMed]
    • Cassotti, M.; Consonni, V.; Mauri, A.; Ballabio, D. Validation and extension of a similarity-based approach for prediction of acute aquatic toxicity towards Daphnia magna. SAR QSAR Environ. Res. 2014, 25, 1013-1036. [CrossRef] [PubMed]
    • (2014) SAR QSAR Environ. Res , vol.25 , pp. 1013-1036
    • Cassotti, M.1    Consonni, V.2    Mauri, A.3    Ballabio, D.4
  • 62
    • 84876972436 scopus 로고    scopus 로고
    • Integration of QSAR models for bioconcentration suitable for REACH
    • [CrossRef] [PubMed]
    • Gissi, A.; Nicolotti, O.; Carotti, A.; Gadaleta, D.; Lombardo, A.; Benfenati, E. Integration of QSAR models for bioconcentration suitable for REACH. Sci. Total Environ. 2013, 456-457, 325-332. [CrossRef] [PubMed]
    • (2013) Sci. Total Environ , vol.456-457 , pp. 325-332
    • Gissi, A.1    Nicolotti, O.2    Carotti, A.3    Gadaleta, D.4    Lombardo, A.5    Benfenati, E.6
  • 63
    • 0030627336 scopus 로고    scopus 로고
    • Role of cytochrome P450 enzymes in drug-drug interactions
    • Fp, G. Role of cytochrome P450 enzymes in drug-drug interactions. Adv. Pharmacol. 1996, 43, 7-35.
    • (1996) Adv. Pharmacol , vol.43 , pp. 7-35
    • Fp, G.1
  • 65
    • 0004117251 scopus 로고
    • Daylight Chemical Information Systems, Inc.: Aliso Viejo, CA, USA
    • James, C.A.; Weininger, D.; Delany, J. Daylight Theory Manual; Daylight Chemical Information Systems, Inc.: Aliso Viejo, CA, USA, 1995; 3951p.
    • (1995) Daylight Theory Manual , pp. 3951
    • James, C.A.1    Weininger, D.2    Delany, J.3
  • 66
    • 0345019845 scopus 로고    scopus 로고
    • Genetic algorithms applied to feature selection in PLS regression: How and when to use them
    • [CrossRef]
    • Leardi, R.; Lupiáñez González, A. Genetic algorithms applied to feature selection in PLS regression: How and when to use them. Chemom. Intell. Lab. Syst. 1998, 41, 195-207. [CrossRef]
    • (1998) Chemom. Intell. Lab. Syst. , vol.41 , pp. 195-207
    • Leardi, R.1    Lupiáñez González, A.2
  • 68
    • 84879995135 scopus 로고    scopus 로고
    • Defining a novel k-Nearest neighbours approach to assess the applicability domain of a QSAR model for reliable predictions
    • [CrossRef] [PubMed]
    • Sahigara, F.; Ballabio, D.; Todeschini, R.; Consonni, V. Defining a novel k-Nearest neighbours approach to assess the applicability domain of a QSAR model for reliable predictions. J. Cheminform. 2013, 5, 27. [CrossRef] [PubMed]
    • (2013) J. Cheminform , vol.5 , pp. 27
    • Sahigara, F.1    Ballabio, D.2    Todeschini, R.3    Consonni, V.4
  • 69
    • 84879557098 scopus 로고    scopus 로고
    • KNIME: The konstanz information miner
    • Preisach, C., Burkhardt, P.D.H., Schmidt-Thieme, P.D.L., Decker, P.D.R., Eds.; Studies in Classification, Data Analysis, and Knowledge Organization; Springer: Berlin, Germany; Heidelberg, Germany
    • Berthold, M.R.; Cebron, N.; Dill, F.; Gabriel, T.R.; Kötter, T.; Meinl, T.; Ohl, P.; Sieb, C.; Thiel, K.; Wiswedel, B. KNIME: The konstanz information miner. In Data Analysis, Machine Learning and Applications; Preisach, C., Burkhardt, P.D.H., Schmidt-Thieme, P.D.L., Decker, P.D.R., Eds.; Studies in Classification, Data Analysis, and Knowledge Organization; Springer: Berlin, Germany; Heidelberg, Germany, 2008; pp. 319-326.
    • (2008) Data Analysis, Machine Learning and Applications , pp. 319-326
    • Berthold, M.R.1    Cebron, N.2    Dill, F.3    Gabriel, T.R.4    Kötter, T.5    Meinl, T.6    Ohl, P.7    Sieb, C.8    Thiel, K.9    Wiswedel, B.10
  • 70
    • 84960463605 scopus 로고    scopus 로고
    • R2015a;: Natick, MA, USA
    • MATLAB, 2015. R2015a; The MathWorks Inc.: Natick, MA, USA, 2015.
    • (2015) The MathWorks Inc
  • 71
    • 84973567848 scopus 로고    scopus 로고
    • (accessed on 3 March 2016)
    • Milano Chemometrics and QSAR Research Group. Available online: http://michem.disat.unimib.it/chm/ download/datasets.htm (accessed on 3 March 2016).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.