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Volumn 44, Issue 1, 2004, Pages 179-186

QSPR Modeling of Lipid-Water Partition Coefficient by Optimization of Correlation Weights of Local Graph Invariants

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CORRELATION METHODS; DRUG PRODUCTS; ENZYMES; GRAPH THEORY; HYDROPHOBICITY; MOLECULAR PHYSICS; OPTIMIZATION; WATER;

EID: 1842640061     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci034200g     Document Type: Article
Times cited : (29)

References (49)
  • 3
    • 0000795719 scopus 로고
    • Hansen, C.; Sammes, P. G.; Taylor, J. B., Eds.; Pergamon Press: Oxford
    • Taylor, P. J. In Comprehensive Medicinal Chemistry; Hansen, C.; Sammes, P. G.; Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 4, pp 241-294.
    • (1990) Comprehensive Medicinal Chemistry , vol.4 , pp. 241-294
    • Taylor, P.J.1
  • 5
    • 0041527330 scopus 로고    scopus 로고
    • Chose, A. K., Viswanadhan, V. N., Eds.; Marcel Dekker: New York
    • Debnath, A. K. In Combinatorial Library Design and Evaluation; Chose, A. K., Viswanadhan, V. N., Eds.; Marcel Dekker: New York, 2001; pp 73-129.
    • (2001) Combinatorial Library Design and Evaluation , pp. 73-129
    • Debnath, A.K.1
  • 8
    • 0025731738 scopus 로고
    • Partitioning of Solutes in Different Solvent Systems: The Contribution of Hydrogen Bonding Capacity and Polarity
    • el Tayar, N.; Tsai, R. S.; Testa, B.; Carrupt, P. A.; Leo, A. Partitioning of Solutes in Different Solvent Systems: The Contribution of Hydrogen Bonding Capacity and Polarity. J. Pharm. Sci. 1991, 80, 590-598.
    • (1991) J. Pharm. Sci. , vol.80 , pp. 590-598
    • El Tayar, N.1    Tsai, R.S.2    Testa, B.3    Carrupt, P.A.4    Leo, A.5
  • 10
    • 0023289451 scopus 로고
    • Atomic Physicochemical Parameters for Three-Dimensional-Structure- Directed Quantitative Structure-Activity Relationships. 2. Modeling Dispersive and Hydrophobic Interactions
    • Ghose, A. K.; Crippen, G. M. Atomic Physicochemical Parameters for Three-Dimensional-Structure-Directed Quantitative Structure-Activity Relationships. 2. Modeling Dispersive and Hydrophobic Interactions. J. Chem. Inf. Comput. Sci. 1987, 27, 21-35.
    • (1987) J. Chem. Inf. Comput. Sci. , vol.27 , pp. 21-35
    • Ghose, A.K.1    Crippen, G.M.2
  • 11
    • 0000381930 scopus 로고    scopus 로고
    • Prediction of Hydrophobic Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods
    • Chose, A. K.; Viswanandhan, V. N.; Wendoloski, J. J. Prediction of Hydrophobic Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods. J. Phys. Chem. 1998, 102, 3762-3772.
    • (1998) J. Phys. Chem. , vol.102 , pp. 3762-3772
    • Chose, A.K.1    Viswanandhan, V.N.2    Wendoloski, J.J.3
  • 12
    • 0024656378 scopus 로고
    • A New Method for The Estimation of Partition Coefficient
    • Bodor, N.; Gabanyi, Z.; Wong, C.-K. A New Method for The Estimation of Partition Coefficient. J. Am. Chem. Soc. 1989, 111, 3783-3786.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3783-3786
    • Bodor, N.1    Gabanyi, Z.2    Wong, C.-K.3
  • 13
    • 84986520724 scopus 로고
    • A Computer Automated Structure Evaluation (CASE) Approach to the Calculation of Partition Coefficients
    • Klopman, G.; Wang, S. A Computer Automated Structure Evaluation (CASE) Approach to the Calculation of Partition Coefficients. J Comput. Chem. 1991, 12, 1025-1032.
    • (1991) J Comput. Chem. , vol.12 , pp. 1025-1032
    • Klopman, G.1    Wang, S.2
  • 15
    • 0025439652 scopus 로고
    • Automatic Log P Estimation Based on Combined Additive Modeling Studies
    • Suzuki, T.; Kudo, Y. Automatic Log P Estimation Based on Combined Additive Modeling Studies. J. Comput. Aided Mol. Des. 1990, 4, 155-198.
    • (1990) J. Comput. Aided Mol. Des. , vol.4 , pp. 155-198
    • Suzuki, T.1    Kudo, Y.2
  • 17
    • 0029049760 scopus 로고
    • Physicochemical Significance of Topological Parameters: Molecular Connectivity Index and Information Content. Part 2. Correlation Studies with Molar Refractivity and Lipophilicity
    • Saxena, A. K. Physicochemical Significance of Topological Parameters: Molecular Connectivity Index and Information Content. Part 2. Correlation Studies with Molar Refractivity and Lipophilicity. Quant. Struct.-Act. Relat. 1995, 14, 142-150.
    • (1995) Quant. Struct.-act. Relat. , vol.14 , pp. 142-150
    • Saxena, A.K.1
  • 19
    • 0031843610 scopus 로고    scopus 로고
    • Understanding and Estimating Membrane-Water Partition Coefficients: Approaches to Derive Quantitative Structure-Property Relationships
    • Vaes, W. H.; Ramos, E. U.; Verhaar, H. J.; Cramer, C, J.; Hermens, J. L. Understanding and Estimating Membrane-Water Partition Coefficients: Approaches to Derive Quantitative Structure-Property Relationships. Chem. Res. Toxicol. 1998, 11, 847-854.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 847-854
    • Vaes, W.H.1    Ramos, E.U.2    Verhaar, H.J.3    Cramer, C.J.4    Hermens, J.L.5
  • 20
    • 0035353669 scopus 로고    scopus 로고
    • 3D Connectivity Indices in QSPR/QSAR Studies
    • Estrada, E.; Molina, E. 3D Connectivity Indices in QSPR/QSAR Studies. J. Chem. Inf. Comput. Sci. 2001, 41, 791-797.
    • (2001) J. Chem. Inf. Comput. Sci. , vol.41 , pp. 791-797
    • Estrada, E.1    Molina, E.2
  • 21
    • 0030121940 scopus 로고    scopus 로고
    • Modeling Lipophilicity from the Distribution of Electrostatic Potential on A Molecular Surface
    • Du, Q.; Arteca, G. A. Modeling Lipophilicity from the Distribution of Electrostatic Potential on A Molecular Surface. J. Comput. Aided Mol. Des. 1996, 10, 133-144.
    • (1996) J. Comput. Aided Mol. Des. , vol.10 , pp. 133-144
    • Du, Q.1    Arteca, G.A.2
  • 22
    • 1842804636 scopus 로고    scopus 로고
    • Comparative QSPR Studies with Molecular Connectivity, Molecular Negentropy and TAU Indices. Part II: Lipid-Water Partition Coefficient of Diverse Functional Acyclic Compounds
    • Roy, K.; Saha, A. Comparative QSPR Studies with Molecular Connectivity, Molecular Negentropy and TAU Indices. Part II: Lipid-Water Partition Coefficient of Diverse Functional Acyclic Compounds. Internet Electron. J. Mol. Des. 2003, 2, 288-305, http://www.biochempress.com.
    • (2003) Internet Electron. J. Mol. Des. , vol.2 , pp. 288-305
    • Roy, K.1    Saha, A.2
  • 23
    • 84986432885 scopus 로고
    • On Computation of Optimal Parameters for Multivariate Analysis of Structure-Property Relationship
    • Randic, M. On Computation of Optimal Parameters for Multivariate Analysis of Structure-Property Relationship. J. Comput. Chem. 1991, 12, 970-980.
    • (1991) J. Comput. Chem. , vol.12 , pp. 970-980
    • Randic, M.1
  • 24
    • 0026073222 scopus 로고
    • Novel Graph Theoretic Approach to Heteroatoms in Quantitative Structure-Activity Relationships
    • Randic, M. Novel Graph Theoretic Approach to Heteroatoms in Quantitative Structure-Activity Relationships. Chemom. Intell. Lab. Syst. 1991, 10, 213-227.
    • (1991) Chemom. Intell. Lab. Syst. , vol.10 , pp. 213-227
    • Randic, M.1
  • 25
    • 0001239360 scopus 로고
    • Resolution of Ambiguities in Structure-Property Studies by Use of Orthogonal Descriptors
    • Randic, M. Resolution of Ambiguities in Structure-Property Studies by Use of Orthogonal Descriptors. J. Chem. Inf. Comput. Sci. 1991, 31, 311-320.
    • (1991) J. Chem. Inf. Comput. Sci. , vol.31 , pp. 311-320
    • Randic, M.1
  • 26
    • 33751392179 scopus 로고
    • Similarity Based on Extended Basic Descriptors
    • Randic, M. Similarity Based on Extended Basic Descriptors. J. Chem. Inf. Comput. Sci. 1992, 32, 686-692.
    • (1992) J. Chem. Inf. Comput. Sci. , vol.32 , pp. 686-692
    • Randic, M.1
  • 27
    • 0029403907 scopus 로고
    • Graph Theoretical Invariants of Randic Revisited
    • Estrada, E. Graph Theoretical Invariants of Randic Revisited. J. Chem. Inf. Comput. Sci. 1995, 35, 1022-1025.
    • (1995) J. Chem. Inf. Comput. Sci. , vol.35 , pp. 1022-1025
    • Estrada, E.1
  • 29
    • 0001760991 scopus 로고    scopus 로고
    • Optimal Molecular Descriptors Based on Weighted Path Numbers
    • Randic, M.; Basak, S. C. Optimal Molecular Descriptors Based on Weighted Path Numbers. J. Chem. Inf. Comput. Sci. 1999, 39, 261-266.
    • (1999) J. Chem. Inf. Comput. Sci. , vol.39 , pp. 261-266
    • Randic, M.1    Basak, S.C.2
  • 30
    • 0009995435 scopus 로고    scopus 로고
    • Sinha, D. K., Basak, S. C., Mohanty, R. K., Basumallick, I. N., Eds.; Visva-Bharati University Press: Santiniketan
    • Randic, M.; Basak, S. C. In Some Aspects in Mathematical Chemistry; Sinha, D. K., Basak, S. C., Mohanty, R. K., Basumallick, I. N., Eds.; Visva-Bharati University Press: Santiniketan; 1999; p 24.
    • (1999) Some Aspects in Mathematical Chemistry , pp. 24
    • Randic, M.1    Basak, S.C.2
  • 31
    • 0345580974 scopus 로고    scopus 로고
    • Optimization of Correlation Weights of the Local Graph Invariants: Use of the Enthalpies of Formation of Complex Compounds for the QSPR Modeling
    • Toropov, A. A.; Toropova, A. P. Optimization of Correlation Weights of the Local Graph Invariants: Use of the Enthalpies of Formation of Complex Compounds for the QSPR Modeling. Russ. J. Coord. Chem. 1998, 24, 81-85.
    • (1998) Russ. J. Coord. Chem. , vol.24 , pp. 81-85
    • Toropov, A.A.1    Toropova, A.P.2
  • 32
    • 1842754115 scopus 로고    scopus 로고
    • Generalized Zero-Order Molecular Connectivity Index: Enthalpies of Crystalline Aquo and Ammino Complexes in QSPR Modeling
    • Toropov, A. A.; Toropova, A. P.; Voropaeva, N. L.; Ruban, I. N.; Rashidova, S. Sh. Generalized Zero-Order Molecular Connectivity Index: Enthalpies of Crystalline Aquo and Ammino Complexes in QSPR Modeling. Russ. J. Coord. Chem. 1998, 24, 525-529.
    • (1998) Russ. J. Coord. Chem. , vol.24 , pp. 525-529
    • Toropov, A.A.1    Toropova, A.P.2    Voropaeva, N.L.3    Ruban, I.N.4    Rashidova, S.Sh.5
  • 33
    • 0033238594 scopus 로고    scopus 로고
    • Quantitative Structure-Property Relationships for Binary Polymer Solvent Systems: Correlation Weighing of the Local Invariants of Molecular Graphs
    • Toropov, A. A.; Voropaeva, N. L.; Ruban, I. N.; Rashidova, S. Sh. Quantitative Structure-Property Relationships for Binary Polymer Solvent Systems: Correlation Weighing of the Local Invariants of Molecular Graphs. Polym. Sci. Sci: A 1999, 41, 975-985.
    • (1999) Polym. Sci. Sci: A , vol.41 , pp. 975-985
    • Toropov, A.A.1    Voropaeva, N.L.2    Ruban, I.N.3    Rashidova, S.Sh.4
  • 34
    • 0035877382 scopus 로고    scopus 로고
    • Improved molecular descriptors to calculate boiling points based on the optimization of correlation weights of local graph invariants
    • Krenkel, G.; Castro, E. A.; Toropov, A. A. Improved molecular descriptors to calculate boiling points based on the optimization of correlation weights of local graph invariants. J. Mol. Struct. (THEOCHEM) 2001, 542, 107-113.
    • (2001) J. Mol. Struct. (THEOCHEM) , vol.542 , pp. 107-113
    • Krenkel, G.1    Castro, E.A.2    Toropov, A.A.3
  • 35
    • 0035789450 scopus 로고    scopus 로고
    • Calculation of Total Molecular Electronic Energies from Correlation Weighting of Local Graph Invariants
    • Mercader, A.; Castro, E. A.; Toropov, A. A. Calculation of Total Molecular Electronic Energies from Correlation Weighting of Local Graph Invariants. J. Mol. Model. 2001, 7, 1-5.
    • (2001) J. Mol. Model. , vol.7 , pp. 1-5
    • Mercader, A.1    Castro, E.A.2    Toropov, A.A.3
  • 36
    • 0000283455 scopus 로고    scopus 로고
    • QSPR Modeling of the Enthalpy of Formation from Elements by Means of Correlation Weighting of Local Invariants of Atomic Orbital Molecular Graphs
    • Mercader, A.; Castro, E. A.; Toropov, A. A. QSPR Modeling of the Enthalpy of Formation from Elements by Means of Correlation Weighting of Local Invariants of Atomic Orbital Molecular Graphs. Chem. Phys. Lett. 2000, 330, 612-623.
    • (2000) Chem. Phys. Lett. , vol.330 , pp. 612-623
    • Mercader, A.1    Castro, E.A.2    Toropov, A.A.3
  • 37
    • 0001829327 scopus 로고    scopus 로고
    • Improved Molecular Descriptors Based on the Optimization of Correlation Weights of Local Graph Invariants
    • Krenkel, G.; Castro, E. A.; Toropov, A. A. Improved Molecular Descriptors Based on the Optimization of Correlation Weights of Local Graph Invariants. Int. J. Mol. Sci. 2001, 2, 57-65. http://www.mdpi.org/ijms.
    • (2001) Int. J. Mol. Sci. , vol.2 , pp. 57-65
    • Krenkel, G.1    Castro, E.A.2    Toropov, A.A.3
  • 38
    • 0012262318 scopus 로고    scopus 로고
    • QSAR Carcinogenic Study of Methylated Polycyclic Aromatic Hydrocarbons Based on Topological Descriptors Derived from Distance Matrices and Correlation Weights of Local Graph Invariants
    • Marino, D. J. G.; Perruzo, P. J.; Castro, E. A.; Toropov, A. A. QSAR Carcinogenic Study of Methylated Polycyclic Aromatic Hydrocarbons Based on Topological Descriptors Derived from Distance Matrices and Correlation Weights of Local Graph Invariants. Internet Electron. J. Mol Des. 2002, 1, 115-133, http://www.biochempress.com.
    • (2002) Internet Electron. J. Mol Des. , vol.1 , pp. 115-133
    • Marino, D.J.G.1    Perruzo, P.J.2    Castro, E.A.3    Toropov, A.A.4
  • 39
    • 0036015549 scopus 로고    scopus 로고
    • Improved QSPR Analysis of Standard Entropy of Acyclic and Aromatic Compounds Using Optimized Correlation Weights of Linear Graph Invariants
    • Duchowicz, P.; Castro, E. A.; Toropov, A. A. Improved QSPR Analysis of Standard Entropy of Acyclic and Aromatic Compounds Using Optimized Correlation Weights of Linear Graph Invariants. Comput. Chem. 2002, 26, 327-332.
    • (2002) Comput. Chem. , vol.26 , pp. 327-332
    • Duchowicz, P.1    Castro, E.A.2    Toropov, A.A.3
  • 40
    • 0347553628 scopus 로고    scopus 로고
    • Structure-Toxicity Relationships for Aliphatic Compounds Based on Correlation Weighting of Local Graph Invariants
    • Toropov, A. A.; Duchowicz, P.; Castro, E. A. Structure-Toxicity Relationships for Aliphatic Compounds Based on Correlation Weighting of Local Graph Invariants. Int. J. Mol Sci. 2003, 4, 272-283, http://www.mdpi.org/ijms.
    • (2003) Int. J. Mol Sci. , vol.4 , pp. 272-283
    • Toropov, A.A.1    Duchowicz, P.2    Castro, E.A.3
  • 41
    • 1842754093 scopus 로고    scopus 로고
    • QSPR Modeling of Lipophilicity By Means of Correlation Weights of Local Graph Invariants
    • Perruzo, P. J.; Marino, D. J. G.; Castro, E. A.; Toropov, A. A. QSPR Modeling of Lipophilicity By Means of Correlation Weights of Local Graph Invariants. Internet Electron. J. Mol Des. 2003, 2, 334-347, http://www.biochempress.com.
    • (2003) Internet Electron. J. Mol Des. , vol.2 , pp. 334-347
    • Perruzo, P.J.1    Marino, D.J.G.2    Castro, E.A.3    Toropov, A.A.4
  • 42
    • 8644243613 scopus 로고
    • Partition Coefficients and Their Uses
    • Leo, A.; Hansch, C.; Elkins, D. Partition Coefficients and Their Uses. Chem. Rev. 1971, 71, 525-616.
    • (1971) Chem. Rev. , vol.71 , pp. 525-616
    • Leo, A.1    Hansch, C.2    Elkins, D.3
  • 43
    • 0001085722 scopus 로고
    • The Linear Free Energy Relationship Between Partition-Coefficients and The Aqueous Solubility of Organic Liquids
    • Hansch, C.; Quinlan, J. E.; Lawrence, G. L. The Linear Free Energy Relationship Between Partition-Coefficients and The Aqueous Solubility of Organic Liquids. J. Org. Chem. 1968, 33, 347-350.
    • (1968) J. Org. Chem. , vol.33 , pp. 347-350
    • Hansch, C.1    Quinlan, J.E.2    Lawrence, G.L.3
  • 44
    • 0000422818 scopus 로고
    • Optimal Characterization of Structures for Prediction of Propertes
    • Basak, S. C.; Niemi, G. J.; Veith, G. D. Optimal Characterization of Structures for Prediction of Propertes. J. Math. Chem. 1990, 4, 185-205.
    • (1990) J. Math. Chem. , vol.4 , pp. 185-205
    • Basak, S.C.1    Niemi, G.J.2    Veith, G.D.3
  • 45
    • 1842754111 scopus 로고    scopus 로고
    • The program for optimization of correlation weights was developed in PASCAL by A. A. Toropov
    • The program for optimization of correlation weights was developed in PASCAL by A. A. Toropov.
  • 46
    • 1842804625 scopus 로고    scopus 로고
    • The GW-BASIC programs RRR98, KRPRESI and KRPRES2 were developed by Kunal Roy (1998) and standardized using known data sets
    • The GW-BASIC programs RRR98, KRPRESI and KRPRES2 were developed by Kunal Roy (1998) and standardized using known data sets.
  • 47
    • 0003633894 scopus 로고
    • Oxford & IBM Publishing Co. Pvt. Ltd.: New Delhi
    • Snedecor, G. W.; Cochran, W. G. Statistical Methods; Oxford & IBM Publishing Co. Pvt. Ltd.: New Delhi, 1967; pp 381-418.
    • (1967) Statistical Methods , pp. 381-418
    • Snedecor, G.W.1    Cochran, W.G.2
  • 48
    • 0026512708 scopus 로고
    • Testa, B., Ed.; Academic Press: New York
    • Kier, L. B.; Hall, L. H. In Advances in Drug Research; Testa, B., Ed.; Academic Press: New York, 1992; Vol. 22, pp 1-38.
    • (1992) Advances in Drug Research , vol.22 , pp. 1-38
    • Kier, L.B.1    Hall, L.H.2


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