Quantum Molecular Similarity. 3. QTMS Descriptors

S. E. O'Brien; P. L A Popelier

doi:10.1021/ci0004661

Quantum Molecular Similarity. 3. QTMS Descriptors

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Abstract

Building on the ideas of a previous paper [part 1, J. Phys. Chem. A 1999, 103, 2883] we present a new molecular similarity method based on the topology of the electron density. This method is directly applicable to QSARs and is called quantum topological molecular similarity (QTMS). It has been tested for five sets of carboxylic systems including para- and meta-benzoic acid, para-phenylacetic acid, 4-X-bicyclo[2.2.2]-octane-1-carboxylic acids, and polysubstituted benzoic acids. In combination with the partial least squares (PLS) procedure QTMS is able to produce excellent and statistically valid regressions. It is shown that QTMS avoids certain challenges of traditional Carbó-like similarity indices. Finally, QTMS is able to suggest a molecular fragment that contains the active center or the part of the molecule that is responsible for the QSAR.

Original language	English
Pages (from-to)	764-775
Number of pages	11
Journal	Journal of Chemical Information and Computer Sciences
Volume	41
Issue number	3
DOIs	https://doi.org/10.1021/ci0004661
Publication status	Published - 2001

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title = "Quantum Molecular Similarity. 3. QTMS Descriptors",

abstract = "Building on the ideas of a previous paper [part 1, J. Phys. Chem. A 1999, 103, 2883] we present a new molecular similarity method based on the topology of the electron density. This method is directly applicable to QSARs and is called quantum topological molecular similarity (QTMS). It has been tested for five sets of carboxylic systems including para- and meta-benzoic acid, para-phenylacetic acid, 4-X-bicyclo[2.2.2]-octane-1-carboxylic acids, and polysubstituted benzoic acids. In combination with the partial least squares (PLS) procedure QTMS is able to produce excellent and statistically valid regressions. It is shown that QTMS avoids certain challenges of traditional Carb{\'o}-like similarity indices. Finally, QTMS is able to suggest a molecular fragment that contains the active center or the part of the molecule that is responsible for the QSAR.",

author = "O'Brien, {S. E.} and Popelier, {P. L A}",

note = "Times Cited: 58 2nd Indo-US Workshop on Mathermatical Chemistry with Applications to Drug Discovery, Cheminformatics, and Bioinformatics May 30-jun 03, 2000 Univ minnesota duluth, duluth, minnesota Univ Minnesota Duluth, Nat Resources Res Inst; Visva Bharati Univ; Santinietan; W Bengal",

year = "2001",

doi = "10.1021/ci0004661",

language = "English",

volume = "41",

pages = "764--775",

journal = "Journal of Chemical Information and Computer Sciences",

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publisher = "American Chemical Society",

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T1 - Quantum Molecular Similarity. 3. QTMS Descriptors

AU - O'Brien, S. E.

AU - Popelier, P. L A

N1 - Times Cited: 58 2nd Indo-US Workshop on Mathermatical Chemistry with Applications to Drug Discovery, Cheminformatics, and Bioinformatics May 30-jun 03, 2000 Univ minnesota duluth, duluth, minnesota Univ Minnesota Duluth, Nat Resources Res Inst; Visva Bharati Univ; Santinietan; W Bengal

PY - 2001

Y1 - 2001

N2 - Building on the ideas of a previous paper [part 1, J. Phys. Chem. A 1999, 103, 2883] we present a new molecular similarity method based on the topology of the electron density. This method is directly applicable to QSARs and is called quantum topological molecular similarity (QTMS). It has been tested for five sets of carboxylic systems including para- and meta-benzoic acid, para-phenylacetic acid, 4-X-bicyclo[2.2.2]-octane-1-carboxylic acids, and polysubstituted benzoic acids. In combination with the partial least squares (PLS) procedure QTMS is able to produce excellent and statistically valid regressions. It is shown that QTMS avoids certain challenges of traditional Carbó-like similarity indices. Finally, QTMS is able to suggest a molecular fragment that contains the active center or the part of the molecule that is responsible for the QSAR.

AB - Building on the ideas of a previous paper [part 1, J. Phys. Chem. A 1999, 103, 2883] we present a new molecular similarity method based on the topology of the electron density. This method is directly applicable to QSARs and is called quantum topological molecular similarity (QTMS). It has been tested for five sets of carboxylic systems including para- and meta-benzoic acid, para-phenylacetic acid, 4-X-bicyclo[2.2.2]-octane-1-carboxylic acids, and polysubstituted benzoic acids. In combination with the partial least squares (PLS) procedure QTMS is able to produce excellent and statistically valid regressions. It is shown that QTMS avoids certain challenges of traditional Carbó-like similarity indices. Finally, QTMS is able to suggest a molecular fragment that contains the active center or the part of the molecule that is responsible for the QSAR.

U2 - 10.1021/ci0004661

DO - 10.1021/ci0004661

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SN - 0095-2338

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SP - 764

EP - 775

JO - Journal of Chemical Information and Computer Sciences

JF - Journal of Chemical Information and Computer Sciences

IS - 3

ER -

Quantum Molecular Similarity. 3. QTMS Descriptors

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