DOI: 10.1021/acs.jpclett.7b00038. Genetic Optimization of Training Sets for Improved Machine Learning Models of Molecular Properties

Genetic Optimization of Training Sets for Improved Machine Learning Models of Molecular Properties

10.1021/acs.jpclett.7b00038

Crossref journal-article

American Chemical Society (ACS)

The Journal of Physical Chemistry Letters (316)

Bibliography

Browning, N. J., Ramakrishnan, R., von Lilienfeld, O. A., & Roethlisberger, U. (2017). Genetic Optimization of Training Sets for Improved Machine Learning Models of Molecular Properties. The Journal of Physical Chemistry Letters, 8(7), 1351â1359.

Authors 4

Nicholas J. Browning (first)
Raghunathan Ramakrishnan (additional)
O. Anatole von Lilienfeld (additional)
Ursula Roethlisberger (additional)

References 37 Referenced 63

{'key': 'ref1/cit1', 'volume-title': 'Essentials of Computational Chemistry: Theories and Models', 'author': 'Cramer C. J.', 'year': '2004', 'edition': '2'} / Essentials of Computational Chemistry: Theories and Models by Cramer C. J. (2004)
10.1103/PhysRevLett.108.058301
10.1021/acs.jctc.5b00099
10.1088/1367-2630/15/9/095003
10.1002/qua.24375
10.1021/acs.jpclett.5b00831
10.1063/1.4928757
Reeves, C. R.; Bush, D. R.InInstance Selection and Construction for Data Mining;Liu, H.; Motoda, H., Eds.Springer US:Boston, MA, 2001; pp339–356. (10.1007/978-1-4757-3359-4_19)
Ventura, D.; Andersen, T.; Martinez, T. R.Artificial Neural Nets and Genetic Algorithms; Proceedings of the International Conference in Alès, France, 1995;Springer Vienna:Vienna, 1995; pp468–471. (10.1007/978-3-7091-7535-4_121)
10.1021/ct400195d
10.1002/qua.24912
10.1021/acs.jpclett.5b00831
10.1063/1.4964627
10.1038/sdata.2014.22
10.1021/ci300415d
Reymond, J.L.; Visini, R.; Awale, M.Fragment-Based Drug Discovery Lessons and Outlook;Wiley:Berlin, 2016; pp57–74. (10.1002/9783527683604.ch03)
10.1021/acs.jctc.5b00141
10.1007/978-0-387-21606-5 / The Elements of Statistical Learning by Hastie T. (2001)
10.2533/chimia.2015.182
{'key': 'ref20/cit20', 'first-page': '11', 'volume-title': 'Computers & Thought', 'author': 'Turing A. M.', 'year': '1995'} / Computers & Thought by Turing A. M. (1995)
{'key': 'ref21/cit21', 'first-page': '45', 'author': 'Barricelli N.', 'year': '1954', 'journal-title': 'Methodos'} / Methodos by Barricelli N. (1954)
10.1071/BI9570484
Godefroid, P.; Khurshid, S.InTools and Algorithms for the Construction and Analysis of Systems;Katoen, J.P.; Stevens, P., Eds.; Lecture Notes in Computer Science;Springer Berlin Heidelberg, 2002; Vol.2280; pp266–280. (10.1007/3-540-46002-0_19)
10.1021/jp070851u
10.1021/jp502475e
10.1093/nar/gkv951
10.1214/aoms/1177728190
10.1214/aoms/1177704472
10.1103/PhysRevB.92.094306
10.1021/ja401184g
{'key': 'ref31/cit31', 'first-page': '129', 'volume': '11', 'author': 'Sastry K.', 'year': '2001', 'journal-title': 'Intelligent Engineering Systems Through Artificial Neural Networks'} / Intelligent Engineering Systems Through Artificial Neural Networks by Sastry K. (2001)
Spears, W.; Anand, V.InMethodologies for Intelligent Systems;Ras, Z.; Zemankova, M., Eds.; Lecture Notes in Computer Science;Springer:Berlin Heidelberg, 1991; Vol.542; pp409–418. (10.1007/3-540-54563-8_104)
{'key': 'ref33/cit33', 'first-page': '301', 'volume-title': 'Foundations of Genetic Algorithms', 'volume': '1', 'author': 'Spears W. M.', 'year': '1991'} / Foundations of Genetic Algorithms by Spears W. M. (1991)
{'key': 'ref34/cit34', 'first-page': '265', 'volume-title': 'Foundations of Genetic Algorithms', 'volume': '1', 'author': 'Eshelman L. J.', 'year': '1991'} / Foundations of Genetic Algorithms by Eshelman L. J. (1991)
{'key': 'ref35/cit35', 'first-page': '30', 'volume': '26', 'author': 'Deb K.', 'year': '1996', 'journal-title': 'Computer Science and Informatics'} / Computer Science and Informatics by Deb K. (1996)
{'volume-title': 'MOPAC2012', 'year': '2012', 'author': 'Stewart J. P.', 'key': 'ref36/cit36'} / MOPAC2012 by Stewart J. P. (2012)
TURBOMOLE V7.1 2016, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989–2007, TURBOMOLE GmbH, since 2007; available fromhttp://www.turbomole.com.

Dates

Type	When
Created	8 years, 5 months ago (March 3, 2017, 1:12 p.m.)
Deposited	2 years, 4 months ago (April 17, 2023, 1:21 a.m.)
Indexed	3 weeks, 5 days ago (July 27, 2025, 3:56 a.m.)
Issued	8 years, 5 months ago (March 13, 2017)
Published	8 years, 5 months ago (March 13, 2017)
Published Online	8 years, 5 months ago (March 13, 2017)
Published Print	8 years, 4 months ago (April 6, 2017)

Funders 1

Schweizerischer Nationalfonds zur F?rderung der Wissenschaftlichen Forschung 10.13039/501100001711 Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
Region: Europe
pri (Trusts, charities, foundations (both public and private))
Labels10
1. Schweizerischer Nationalfonds
2. Swiss National Science Foundation
3. Fonds National Suisse de la Recherche Scientifique
4. Fondo Nazionale Svizzero per la Ricerca Scientifica
5. Fonds National Suisse
6. Fondo Nazionale Svizzero
7. Schweizerische Nationalfonds
8. SNF
9. SNSF
10. FNS
Awards1
1. 200020_130082/1

BibTeX

@article{Browning_2017, title={Genetic Optimization of Training Sets for Improved Machine Learning Models of Molecular Properties}, volume={8}, ISSN={1948-7185}, url={http://dx.doi.org/10.1021/acs.jpclett.7b00038}, DOI={10.1021/acs.jpclett.7b00038}, number={7}, journal={The Journal of Physical Chemistry Letters}, publisher={American Chemical Society (ACS)}, author={Browning, Nicholas J. and Ramakrishnan, Raghunathan and von Lilienfeld, O. Anatole and Roethlisberger, Ursula}, year={2017}, month=mar, pages={1351–1359} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        27
      ]
    ],
    "date-time": "2025-07-27T07:56:01Z",
    "timestamp": 1753602961203,
    "version": "3.37.3"
  },
  "reference-count": 37,
  "publisher": "American Chemical Society (ACS)",
  "issue": "7",
  "funder": [
    {
      "DOI": "10.13039/501100001711",
      "name": "Schweizerischer Nationalfonds zur F?rderung der Wissenschaftlichen Forschung",
      "doi-asserted-by": "publisher",
      "award": [
        "200020_130082/1"
      ],
      "id": [
        {
          "id": "10.13039/501100001711",
          "id-type": "DOI",
          "asserted-by": "publisher"
        }
      ]
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2017,
        4,
        6
      ]
    ]
  },
  "DOI": "10.1021/acs.jpclett.7b00038",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2017,
        3,
        3
      ]
    ],
    "date-time": "2017-03-03T18:12:29Z",
    "timestamp": 1488564749000
  },
  "page": "1351-1359",
  "source": "Crossref",
  "is-referenced-by-count": 63,
  "title": "Genetic Optimization of Training Sets for Improved Machine Learning Models of Molecular Properties",
  "prefix": "10.1021",
  "volume": "8",
  "author": [
    {
      "ORCID": "https://orcid.org/0000-0002-7859-6495",
      "authenticated-orcid": true,
      "given": "Nicholas J.",
      "family": "Browning",
      "sequence": "first",
      "affiliation": [
        {
          "name": "Laboratory\rof Computational Chemistry and Biochemistry, Institute of Chemical\rSciences and Engineering, Swiss Federal Institute of Technology (EPFL) CH-1015 Lausanne, Switzerland"
        }
      ]
    },
    {
      "given": "Raghunathan",
      "family": "Ramakrishnan",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "O. Anatole",
      "family": "von Lilienfeld",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Ursula",
      "family": "Roethlisberger",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Laboratory\rof Computational Chemistry and Biochemistry, Institute of Chemical\rSciences and Engineering, Swiss Federal Institute of Technology (EPFL) CH-1015 Lausanne, Switzerland"
        }
      ]
    }
  ],
  "member": "316",
  "published-online": {
    "date-parts": [
      [
        2017,
        3,
        13
      ]
    ]
  },
  "reference": [
    {
      "key": "ref1/cit1",
      "volume-title": "Essentials of Computational Chemistry: Theories and Models",
      "author": "Cramer C. J.",
      "year": "2004",
      "edition": "2"
    },
    {
      "key": "ref2/cit2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1103/PhysRevLett.108.058301"
    },
    {
      "key": "ref3/cit3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/acs.jctc.5b00099"
    },
    {
      "key": "ref4/cit4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1088/1367-2630/15/9/095003"
    },
    {
      "key": "ref5/cit5",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/qua.24375"
    },
    {
      "key": "ref6/cit6",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/acs.jpclett.5b00831"
    },
    {
      "key": "ref7/cit7",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.4928757"
    },
    {
      "key": "ref8/cit8",
      "doi-asserted-by": "crossref",
      "unstructured": "Reeves, C. R.; Bush, D. R.InInstance Selection and Construction for Data Mining;Liu, H.; Motoda, H., Eds.Springer US:Boston, MA, 2001; pp339\u2013356.",
      "DOI": "10.1007/978-1-4757-3359-4_19"
    },
    {
      "key": "ref9/cit9",
      "doi-asserted-by": "crossref",
      "unstructured": "Ventura, D.; Andersen, T.; Martinez, T. R.Artificial Neural Nets and Genetic Algorithms; Proceedings of the International Conference in Al\u00e8s, France, 1995;Springer Vienna:Vienna, 1995; pp468\u2013471.",
      "DOI": "10.1007/978-3-7091-7535-4_121"
    },
    {
      "key": "ref10/cit10",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ct400195d"
    },
    {
      "key": "ref11/cit11",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/qua.24912"
    },
    {
      "key": "ref12/cit12",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/acs.jpclett.5b00831"
    },
    {
      "key": "ref13/cit13",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.4964627"
    },
    {
      "key": "ref14/cit14",
      "doi-asserted-by": "publisher",
      "DOI": "10.1038/sdata.2014.22"
    },
    {
      "key": "ref15/cit15",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ci300415d"
    },
    {
      "key": "ref16/cit16",
      "doi-asserted-by": "crossref",
      "unstructured": "Reymond, J.L.; Visini, R.; Awale, M.Fragment-Based Drug Discovery Lessons and Outlook;Wiley:Berlin, 2016; pp57\u201374.",
      "DOI": "10.1002/9783527683604.ch03"
    },
    {
      "key": "ref17/cit17",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/acs.jctc.5b00141"
    },
    {
      "key": "ref18/cit18",
      "doi-asserted-by": "crossref",
      "DOI": "10.1007/978-0-387-21606-5",
      "volume-title": "The Elements of Statistical Learning",
      "author": "Hastie T.",
      "year": "2001"
    },
    {
      "key": "ref19/cit19",
      "doi-asserted-by": "publisher",
      "DOI": "10.2533/chimia.2015.182"
    },
    {
      "key": "ref20/cit20",
      "first-page": "11",
      "volume-title": "Computers & Thought",
      "author": "Turing A. M.",
      "year": "1995"
    },
    {
      "key": "ref21/cit21",
      "first-page": "45",
      "author": "Barricelli N.",
      "year": "1954",
      "journal-title": "Methodos"
    },
    {
      "key": "ref22/cit22",
      "doi-asserted-by": "publisher",
      "DOI": "10.1071/BI9570484"
    },
    {
      "key": "ref23/cit23",
      "doi-asserted-by": "crossref",
      "unstructured": "Godefroid, P.; Khurshid, S.InTools and Algorithms for the Construction and Analysis of Systems;Katoen, J.P.; Stevens, P., Eds.; Lecture Notes in Computer Science;Springer Berlin Heidelberg, 2002; Vol.2280; pp266\u2013280.",
      "DOI": "10.1007/3-540-46002-0_19"
    },
    {
      "key": "ref24/cit24",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jp070851u"
    },
    {
      "key": "ref25/cit25",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jp502475e"
    },
    {
      "key": "ref26/cit26",
      "doi-asserted-by": "publisher",
      "DOI": "10.1093/nar/gkv951"
    },
    {
      "key": "ref27/cit27",
      "doi-asserted-by": "publisher",
      "DOI": "10.1214/aoms/1177728190"
    },
    {
      "key": "ref28/cit28",
      "doi-asserted-by": "publisher",
      "DOI": "10.1214/aoms/1177704472"
    },
    {
      "key": "ref29/cit29",
      "doi-asserted-by": "publisher",
      "DOI": "10.1103/PhysRevB.92.094306"
    },
    {
      "key": "ref30/cit30",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja401184g"
    },
    {
      "key": "ref31/cit31",
      "first-page": "129",
      "volume": "11",
      "author": "Sastry K.",
      "year": "2001",
      "journal-title": "Intelligent Engineering Systems Through Artificial Neural Networks"
    },
    {
      "key": "ref32/cit32",
      "doi-asserted-by": "crossref",
      "unstructured": "Spears, W.; Anand, V.InMethodologies for Intelligent Systems;Ras, Z.; Zemankova, M., Eds.; Lecture Notes in Computer Science;Springer:Berlin Heidelberg, 1991; Vol.542; pp409\u2013418.",
      "DOI": "10.1007/3-540-54563-8_104"
    },
    {
      "key": "ref33/cit33",
      "first-page": "301",
      "volume-title": "Foundations of Genetic Algorithms",
      "volume": "1",
      "author": "Spears W. M.",
      "year": "1991"
    },
    {
      "key": "ref34/cit34",
      "first-page": "265",
      "volume-title": "Foundations of Genetic Algorithms",
      "volume": "1",
      "author": "Eshelman L. J.",
      "year": "1991"
    },
    {
      "key": "ref35/cit35",
      "first-page": "30",
      "volume": "26",
      "author": "Deb K.",
      "year": "1996",
      "journal-title": "Computer Science and Informatics"
    },
    {
      "volume-title": "MOPAC2012",
      "year": "2012",
      "author": "Stewart J. P.",
      "key": "ref36/cit36"
    },
    {
      "key": "ref37/cit37",
      "unstructured": "TURBOMOLE V7.1 2016, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989\u20132007, TURBOMOLE GmbH, since 2007; available fromhttp://www.turbomole.com."
    }
  ],
  "container-title": "The Journal of Physical Chemistry Letters",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://pubs.acs.org/doi/pdf/10.1021/acs.jpclett.7b00038",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        4,
        17
      ]
    ],
    "date-time": "2023-04-17T05:21:47Z",
    "timestamp": 1681708907000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://pubs.acs.org/doi/10.1021/acs.jpclett.7b00038"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2017,
        3,
        13
      ]
    ]
  },
  "references-count": 37,
  "journal-issue": {
    "issue": "7",
    "published-print": {
      "date-parts": [
        [
          2017,
          4,
          6
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1021/acs.jpclett.7b00038"
  ],
  "URL": "http://dx.doi.org/10.1021/acs.jpclett.7b00038",
  "relation": {},
  "ISSN": [
    "1948-7185",
    "1948-7185"
  ],
  "subject": [],
  "container-title-short": "J. Phys. Chem. Lett.",
  "published": {
    "date-parts": [
      [
        2017,
        3,
        13
      ]
    ]
  }
}