DOI: 10.1021/ci5005288. How Accurately Can We Predict the Melting Points of Drug-like Compounds?

How Accurately Can We Predict the Melting Points of Drug-like Compounds?

10.1021/ci5005288

Crossref journal-article

American Chemical Society (ACS)

Journal of Chemical Information and Modeling (316)

Bibliography

Tetko, I. V., Sushko, Y., Novotarskyi, S., Patiny, L., Kondratov, I., Petrenko, A. E., Charochkina, L., & Asiri, A. M. (2014). How Accurately Can We Predict the Melting Points of Drug-like Compounds? Journal of Chemical Information and Modeling, 54(12), 3320â3329.

Authors 8

Igor V. Tetko (first)
Yurii Sushko (additional)
Sergii Novotarskyi (additional)
Luc Patiny (additional)
Ivan Kondratov (additional)
Alexander E. Petrenko (additional)
Larisa Charochkina (additional)
Abdullah M. Asiri (additional)

References 54 Referenced 80

10.1021/ci010287z / J. Chem. Inf. Comput. Sci. by Ran Y. (2001)
10.1002/cite.330370802 / Chem. Ing. Technol. by Irmann F. (1965)
10.1023/A:1008715521862 / Perspect. Drug Discovery Des. by Meylan W. M. (2000)
10.1021/ci600493x / J. Chem. Inf. Model. by Varnek A. (2007)
10.1021/cr900238d / Chem. Rev. by Katritzky A. R. (2010)
{'key': 'ref6/cit6', 'first-page': '241', 'volume-title': 'Computational Toxicology: Risk Assessment for Pharmaceutical and Environmental Chemicals', 'volume': '1', 'author': 'Tetko I. V.', 'year': '2007'} / Computational Toxicology: Risk Assessment for Pharmaceutical and Environmental Chemicals by Tetko I. V. (2007)
10.1080/1062936X.2013.773372 / SAR QSAR Environ. Res. by Dearden J. C. (2013)
{'key': 'ref8/cit8', 'first-page': '1', 'volume': '315', 'author': 'Gavezzotti A.', 'year': '2012', 'journal-title': 'Top. Curr. Chem.'} / Top. Curr. Chem. by Gavezzotti A. (2012)
10.1002/minf.201000133 / Mol. Inf. by Bhhatarai B. (2011)
10.1021/ci060149f / J. Chem. Inf. Model. by Nigsch F. (2006)
10.1186/1758-2946-6-10 / J. Cheminf. by Krstajic D. (2014)
10.1002/minf.201200131 / Mol. Inf. by Sahlin U. (2014)
10.1021/ci0500132 / J. Chem. Inf. Model. by Karthikeyan M. (2005)
10.1021/ci020280x / J. Chem. Inf. Comput. Sci. by Bergström C. A. (2003)
10.1021/ci700307p / J. Chem. Inf. Model. by Hughes L. D. (2008)
10.1007/s10822-011-9440-2 / J. Comput.-Aided Mol. Des. by Sushko I. (2011)
Bradley, J.C.; Lang, A.; Williams, A.Jean-Claude Bradley Double Plus Good (Highly Curated and Validated) Melting Point Dataset.http://dx.doi.org/10.6084/m9.figshare.1031638(accessed November 15, 2014) .
Bradley, J. C.; Lang, A. S. I. D.; Williams, A. J.; Curtin, E.ONS Open Melting Point Collection.http://dx.doi.org/10.1038/npre.2011.6229.1(accessed November 15, 2014) .
10.1177/026119290503300209 / Altern. Lab. Anim. by Netzeva T. I. (2005)
10.1016/j.drudis.2006.06.013 / Drug Discovery Today by Tetko I. V. (2006)
ChemExper.http://www.chemexper.com(accessed November 15, 2014) .
EPA U.S. Environmental Protection Agency EPI Suite v 4.10. http://www.epa.gov/opptintr/exposure/pubs/episuitedl.htm(accessed November 15, 2014) .
MDPI.http://www.mdpi.org/cumbase.htm(accessed November 15, 2014) .
ONSMP.http://onswebservices.wikispaces.com(accessed November 15, 2014) .
10.1177/026119291404200104 / Altern. Lab. Anim. by Brandmaier S. (2014)
ENAMINE Ltd.http://www.enamine.net(accessed November 15, 2014) .
OptiMelt.http://www.thinksrs.com/products/MPA100.htm(accessed November 15, 2014) .
{'key': 'ref28/cit28', 'first-page': '185', 'volume': '458', 'author': 'Tetko I. V.', 'year': '2008', 'journal-title': 'Methods Mol. Biol.'} / Methods Mol. Biol. by Tetko I. V. (2008)
10.1023/A:1019903710291 / Neur. Proc. Lett. by Tetko I. V. (2002)
10.1021/ci010379o / J. Chem. Inf. Comput. Sci. by Tetko I. V. (2002)
OCHEM.http://www.ochem.eu(accessed November 15, 2014) .
10.1021/ci00028a014 / J. Chem. Inf. Comput. Sci. by Hall L. H. (1995)
10.2174/157340908785747465 / Curr. Comput.-Aided Drug Des. by Varnek A. (2008)
10.1016/S0166-1280(98)00467-9 / J. Mol. Struct. by Skvortsova M. I. (1999)
10.1021/ci025584y / J. Chem. Inf. Comput. Sci. by Steinbeck C. (2003)
Todeschini, R.; Consonni, V.Handbook of Molecular Descriptors;Wiley-VCH:Weinheim, 2000; p667. (10.1002/9783527613106)
10.1021/jm0608964 / J. Med. Chem. by Gasteiger J. (2006)
10.3390/molecules15085079 / Molecules by Haider N. (2010)
10.1021/ci00020a039 / J. Chem. Inf. Comput. Sci. by Sadowski J. (1994)
10.1021/ci100253r / J. Chem. Inf. Model. by Sushko I. (2010)
10.1021/ci800151m / J. Chem. Inf. Model. by Tetko I. V. (2008)
{'volume-title': 'Applicability domain of QSAR models', 'year': '2011', 'author': 'Sushko I.', 'key': 'ref42/cit42'} / Applicability domain of QSAR models by Sushko I. (2011)
10.1002/minf.201300030 / Mol. Inf. by Vorberg S. (2014)
10.1021/ci049744c / J. Chem. Inf. Model. by Clark M. (2005)
10.1002/jps.20634 / J. Pharm. Sci. by Jain A. (2006)
10.1021/ci300245q / J. Chem. Inf. Model. by Sushko I. (2012)
10.1177/026119290503300508 / Altern. Lab. Anim. by Jaworska J. (2005)
10.1021/ci400213d / J. Chem. Inf. Model. by Tetko I. V. (2013)
10.1186/1758-2946-5-4 / J. Cheminform. by Oprisiu I. (2013)
10.1021/ci400482e / J. Chem. Inf. Model. by Sheridan R. P. (2013)
10.1186/1758-2946-6-34 / J. Cheminf. by Clark R. D. (2014)
10.1021/ci3000198 / J. Chem. Inf. Model. by Brandmaier S. (2012)
10.1021/ci5001168 / J. Chem. Inf. Model. by Norinder U. (2014)
10.1007/s10822-013-9639-5 / J. Comput.-Aided. Mol. Des. by Wood D. J. (2013)

Dates

Type	When
Created	10 years, 8 months ago (Dec. 9, 2014, 2:04 p.m.)
Deposited	2 years, 4 months ago (April 17, 2023, 7:18 p.m.)
Indexed	1 month ago (July 30, 2025, 11:32 a.m.)
Issued	10 years, 8 months ago (Dec. 9, 2014)
Published	10 years, 8 months ago (Dec. 9, 2014)
Published Online	10 years, 8 months ago (Dec. 9, 2014)
Published Print	10 years, 8 months ago (Dec. 22, 2014)

Funders 1

Russian Scientific Foundation
Awards1
1. 14-43-00024

BibTeX

@article{Tetko_2014, title={How Accurately Can We Predict the Melting Points of Drug-like Compounds?}, volume={54}, ISSN={1549-960X}, url={http://dx.doi.org/10.1021/ci5005288}, DOI={10.1021/ci5005288}, number={12}, journal={Journal of Chemical Information and Modeling}, publisher={American Chemical Society (ACS)}, author={Tetko, Igor V. and Sushko, Yurii and Novotarskyi, Sergii and Patiny, Luc and Kondratov, Ivan and Petrenko, Alexander E. and Charochkina, Larisa and Asiri, Abdullah M.}, year={2014}, month=dec, pages={3320–3329} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        30
      ]
    ],
    "date-time": "2025-07-30T15:32:53Z",
    "timestamp": 1753889573350,
    "version": "3.37.3"
  },
  "reference-count": 54,
  "publisher": "American Chemical Society (ACS)",
  "issue": "12",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2015,
            12,
            9
          ]
        ],
        "date-time": "2015-12-09T00:00:00Z",
        "timestamp": 1449619200000
      },
      "content-version": "vor",
      "delay-in-days": 365,
      "URL": "http://pubs.acs.org/page/policy/authorchoice_termsofuse.html"
    }
  ],
  "funder": [
    {
      "name": "Russian Scientific Foundation",
      "award": [
        "14-43-00024"
      ]
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2014,
        12,
        22
      ]
    ]
  },
  "DOI": "10.1021/ci5005288",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2014,
        12,
        9
      ]
    ],
    "date-time": "2014-12-09T19:04:08Z",
    "timestamp": 1418151848000
  },
  "page": "3320-3329",
  "source": "Crossref",
  "is-referenced-by-count": 80,
  "title": "How Accurately Can We Predict the Melting Points of Drug-like Compounds?",
  "prefix": "10.1021",
  "volume": "54",
  "author": [
    {
      "given": "Igor V.",
      "family": "Tetko",
      "sequence": "first",
      "affiliation": [
        {
          "name": "Helmholtz-Zentrum\rM\u00fcnchen - German Research Centre for Environmental Health (GmbH), Institute of Structural Biology, Munich 85764, Germany"
        },
        {
          "name": "Faculty\rof Science, Chemistry Department, King Abdulaziz University, Jeddah, Makkah 22254, Saudi Arabia"
        },
        {
          "name": "eADMET GmbH, Garching 85748, Germany"
        },
        {
          "name": "A.M.\rButlerov Institute of Chemistry, Kazan Federal University, Kremlyovskaya\rSt. 18, 420008 Kazan, Russia"
        }
      ]
    },
    {
      "given": "Yurii",
      "family": "Sushko",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "eADMET GmbH, Garching 85748, Germany"
        }
      ]
    },
    {
      "given": "Sergii",
      "family": "Novotarskyi",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "eADMET GmbH, Garching 85748, Germany"
        }
      ]
    },
    {
      "given": "Luc",
      "family": "Patiny",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Ecole\rPolytechnique F\u00e9d\u00e9rale de Lausanne (EPFL), Institute of Chemical Sciences and Engineering (ISIC), 1015 Lausanne, Switzerland"
        }
      ]
    },
    {
      "given": "Ivan",
      "family": "Kondratov",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Enamine Ltd., 23 Alexandra\rMatrosova Street, 01103, Kyiv, Ukraine"
        },
        {
          "name": "Institute of Bioorganic\rand Petrochemistry, 1 Murmanskaya Street, 02660, Kyiv, Ukraine"
        }
      ]
    },
    {
      "given": "Alexander E.",
      "family": "Petrenko",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Enamine Ltd., 23 Alexandra\rMatrosova Street, 01103, Kyiv, Ukraine"
        }
      ]
    },
    {
      "given": "Larisa",
      "family": "Charochkina",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Institute of Bioorganic\rand Petrochemistry, 1 Murmanskaya Street, 02660, Kyiv, Ukraine"
        }
      ]
    },
    {
      "given": "Abdullah M.",
      "family": "Asiri",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Faculty\rof Science, Chemistry Department, King Abdulaziz University, Jeddah, Makkah 22254, Saudi Arabia"
        },
        {
          "name": "Center\rof Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, Makkah 21589, Saudi Arabia"
        }
      ]
    }
  ],
  "member": "316",
  "published-online": {
    "date-parts": [
      [
        2014,
        12,
        9
      ]
    ]
  },
  "reference": [
    {
      "key": "ref1/cit1",
      "doi-asserted-by": "crossref",
      "first-page": "1208",
      "DOI": "10.1021/ci010287z",
      "volume": "41",
      "author": "Ran Y.",
      "year": "2001",
      "journal-title": "J. Chem. Inf. Comput. Sci."
    },
    {
      "key": "ref2/cit2",
      "doi-asserted-by": "crossref",
      "first-page": "789",
      "DOI": "10.1002/cite.330370802",
      "volume": "37",
      "author": "Irmann F.",
      "year": "1965",
      "journal-title": "Chem. Ing. Technol."
    },
    {
      "key": "ref3/cit3",
      "doi-asserted-by": "crossref",
      "first-page": "67",
      "DOI": "10.1023/A:1008715521862",
      "volume": "19",
      "author": "Meylan W. M.",
      "year": "2000",
      "journal-title": "Perspect. Drug Discovery Des."
    },
    {
      "key": "ref4/cit4",
      "doi-asserted-by": "crossref",
      "first-page": "1111",
      "DOI": "10.1021/ci600493x",
      "volume": "47",
      "author": "Varnek A.",
      "year": "2007",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref5/cit5",
      "doi-asserted-by": "crossref",
      "first-page": "5714",
      "DOI": "10.1021/cr900238d",
      "volume": "110",
      "author": "Katritzky A. R.",
      "year": "2010",
      "journal-title": "Chem. Rev."
    },
    {
      "key": "ref6/cit6",
      "first-page": "241",
      "volume-title": "Computational Toxicology: Risk Assessment for Pharmaceutical and Environmental Chemicals",
      "volume": "1",
      "author": "Tetko I. V.",
      "year": "2007"
    },
    {
      "key": "ref7/cit7",
      "doi-asserted-by": "crossref",
      "first-page": "279",
      "DOI": "10.1080/1062936X.2013.773372",
      "volume": "24",
      "author": "Dearden J. C.",
      "year": "2013",
      "journal-title": "SAR QSAR Environ. Res."
    },
    {
      "key": "ref8/cit8",
      "first-page": "1",
      "volume": "315",
      "author": "Gavezzotti A.",
      "year": "2012",
      "journal-title": "Top. Curr. Chem."
    },
    {
      "key": "ref9/cit9",
      "doi-asserted-by": "crossref",
      "first-page": "189",
      "DOI": "10.1002/minf.201000133",
      "volume": "30",
      "author": "Bhhatarai B.",
      "year": "2011",
      "journal-title": "Mol. Inf."
    },
    {
      "key": "ref10/cit10",
      "doi-asserted-by": "crossref",
      "first-page": "2412",
      "DOI": "10.1021/ci060149f",
      "volume": "46",
      "author": "Nigsch F.",
      "year": "2006",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref11/cit11",
      "doi-asserted-by": "crossref",
      "first-page": "10",
      "DOI": "10.1186/1758-2946-6-10",
      "volume": "6",
      "author": "Krstajic D.",
      "year": "2014",
      "journal-title": "J. Cheminf."
    },
    {
      "key": "ref12/cit12",
      "doi-asserted-by": "crossref",
      "first-page": "26",
      "DOI": "10.1002/minf.201200131",
      "volume": "33",
      "author": "Sahlin U.",
      "year": "2014",
      "journal-title": "Mol. Inf."
    },
    {
      "key": "ref13/cit13",
      "doi-asserted-by": "crossref",
      "first-page": "581",
      "DOI": "10.1021/ci0500132",
      "volume": "45",
      "author": "Karthikeyan M.",
      "year": "2005",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref14/cit14",
      "doi-asserted-by": "crossref",
      "first-page": "1177",
      "DOI": "10.1021/ci020280x",
      "volume": "43",
      "author": "Bergstr\u00f6m C. A.",
      "year": "2003",
      "journal-title": "J. Chem. Inf. Comput. Sci."
    },
    {
      "key": "ref15/cit15",
      "doi-asserted-by": "crossref",
      "first-page": "220",
      "DOI": "10.1021/ci700307p",
      "volume": "48",
      "author": "Hughes L. D.",
      "year": "2008",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref16/cit16",
      "doi-asserted-by": "crossref",
      "first-page": "533",
      "DOI": "10.1007/s10822-011-9440-2",
      "volume": "25",
      "author": "Sushko I.",
      "year": "2011",
      "journal-title": "J. Comput.-Aided Mol. Des."
    },
    {
      "key": "ref17/cit17",
      "unstructured": "Bradley, J.C.; Lang, A.; Williams, A.Jean-Claude Bradley Double Plus Good (Highly Curated and Validated) Melting Point Dataset.http://dx.doi.org/10.6084/m9.figshare.1031638(accessed November 15, 2014) ."
    },
    {
      "key": "ref18/cit18",
      "unstructured": "Bradley, J. C.; Lang, A. S. I. D.; Williams, A. J.; Curtin, E.ONS Open Melting Point Collection.http://dx.doi.org/10.1038/npre.2011.6229.1(accessed November 15, 2014) ."
    },
    {
      "key": "ref19/cit19",
      "doi-asserted-by": "crossref",
      "first-page": "155",
      "DOI": "10.1177/026119290503300209",
      "volume": "33",
      "author": "Netzeva T. I.",
      "year": "2005",
      "journal-title": "Altern. Lab. Anim."
    },
    {
      "key": "ref20/cit20",
      "doi-asserted-by": "crossref",
      "first-page": "700",
      "DOI": "10.1016/j.drudis.2006.06.013",
      "volume": "11",
      "author": "Tetko I. V.",
      "year": "2006",
      "journal-title": "Drug Discovery Today"
    },
    {
      "key": "ref21/cit21",
      "unstructured": "ChemExper.http://www.chemexper.com(accessed November 15, 2014) ."
    },
    {
      "key": "ref22/cit22",
      "unstructured": "EPA U.S. Environmental Protection Agency EPI Suite v 4.10. http://www.epa.gov/opptintr/exposure/pubs/episuitedl.htm(accessed November 15, 2014) ."
    },
    {
      "key": "ref23/cit23",
      "unstructured": "MDPI.http://www.mdpi.org/cumbase.htm(accessed November 15, 2014) ."
    },
    {
      "key": "ref24/cit24",
      "unstructured": "ONSMP.http://onswebservices.wikispaces.com(accessed November 15, 2014) ."
    },
    {
      "key": "ref25/cit25",
      "doi-asserted-by": "crossref",
      "first-page": "13",
      "DOI": "10.1177/026119291404200104",
      "volume": "42",
      "author": "Brandmaier S.",
      "year": "2014",
      "journal-title": "Altern. Lab. Anim."
    },
    {
      "key": "ref26/cit26",
      "unstructured": "ENAMINE Ltd.http://www.enamine.net(accessed November 15, 2014) ."
    },
    {
      "key": "ref27/cit27",
      "unstructured": "OptiMelt.http://www.thinksrs.com/products/MPA100.htm(accessed November 15, 2014) ."
    },
    {
      "key": "ref28/cit28",
      "first-page": "185",
      "volume": "458",
      "author": "Tetko I. V.",
      "year": "2008",
      "journal-title": "Methods Mol. Biol."
    },
    {
      "key": "ref29/cit29",
      "doi-asserted-by": "crossref",
      "first-page": "187",
      "DOI": "10.1023/A:1019903710291",
      "volume": "16",
      "author": "Tetko I. V.",
      "year": "2002",
      "journal-title": "Neur. Proc. Lett."
    },
    {
      "key": "ref30/cit30",
      "doi-asserted-by": "crossref",
      "first-page": "717",
      "DOI": "10.1021/ci010379o",
      "volume": "42",
      "author": "Tetko I. V.",
      "year": "2002",
      "journal-title": "J. Chem. Inf. Comput. Sci."
    },
    {
      "key": "ref31/cit31",
      "unstructured": "OCHEM.http://www.ochem.eu(accessed November 15, 2014) ."
    },
    {
      "key": "ref32/cit32",
      "doi-asserted-by": "crossref",
      "first-page": "1039",
      "DOI": "10.1021/ci00028a014",
      "volume": "35",
      "author": "Hall L. H.",
      "year": "1995",
      "journal-title": "J. Chem. Inf. Comput. Sci."
    },
    {
      "key": "ref33/cit33",
      "doi-asserted-by": "crossref",
      "first-page": "191",
      "DOI": "10.2174/157340908785747465",
      "volume": "4",
      "author": "Varnek A.",
      "year": "2008",
      "journal-title": "Curr. Comput.-Aided Drug Des."
    },
    {
      "key": "ref34/cit34",
      "doi-asserted-by": "crossref",
      "first-page": "211",
      "DOI": "10.1016/S0166-1280(98)00467-9",
      "volume": "466",
      "author": "Skvortsova M. I.",
      "year": "1999",
      "journal-title": "J. Mol. Struct."
    },
    {
      "key": "ref35/cit35",
      "doi-asserted-by": "crossref",
      "first-page": "493",
      "DOI": "10.1021/ci025584y",
      "volume": "43",
      "author": "Steinbeck C.",
      "year": "2003",
      "journal-title": "J. Chem. Inf. Comput. Sci."
    },
    {
      "key": "ref36/cit36",
      "doi-asserted-by": "crossref",
      "unstructured": "Todeschini, R.; Consonni, V.Handbook of Molecular Descriptors;Wiley-VCH:Weinheim, 2000; p667.",
      "DOI": "10.1002/9783527613106"
    },
    {
      "key": "ref37/cit37",
      "doi-asserted-by": "crossref",
      "first-page": "6429",
      "DOI": "10.1021/jm0608964",
      "volume": "49",
      "author": "Gasteiger J.",
      "year": "2006",
      "journal-title": "J. Med. Chem."
    },
    {
      "key": "ref38/cit38",
      "doi-asserted-by": "crossref",
      "first-page": "5079",
      "DOI": "10.3390/molecules15085079",
      "volume": "15",
      "author": "Haider N.",
      "year": "2010",
      "journal-title": "Molecules"
    },
    {
      "key": "ref39/cit39",
      "doi-asserted-by": "crossref",
      "first-page": "1000",
      "DOI": "10.1021/ci00020a039",
      "volume": "34",
      "author": "Sadowski J.",
      "year": "1994",
      "journal-title": "J. Chem. Inf. Comput. Sci."
    },
    {
      "key": "ref40/cit40",
      "doi-asserted-by": "crossref",
      "first-page": "2094",
      "DOI": "10.1021/ci100253r",
      "volume": "50",
      "author": "Sushko I.",
      "year": "2010",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref41/cit41",
      "doi-asserted-by": "crossref",
      "first-page": "1733",
      "DOI": "10.1021/ci800151m",
      "volume": "48",
      "author": "Tetko I. V.",
      "year": "2008",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "volume-title": "Applicability domain of QSAR models",
      "year": "2011",
      "author": "Sushko I.",
      "key": "ref42/cit42"
    },
    {
      "key": "ref43/cit43",
      "doi-asserted-by": "crossref",
      "first-page": "73",
      "DOI": "10.1002/minf.201300030",
      "volume": "33",
      "author": "Vorberg S.",
      "year": "2014",
      "journal-title": "Mol. Inf."
    },
    {
      "key": "ref44/cit44",
      "doi-asserted-by": "crossref",
      "first-page": "30",
      "DOI": "10.1021/ci049744c",
      "volume": "45",
      "author": "Clark M.",
      "year": "2005",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref45/cit45",
      "doi-asserted-by": "crossref",
      "first-page": "2562",
      "DOI": "10.1002/jps.20634",
      "volume": "95",
      "author": "Jain A.",
      "year": "2006",
      "journal-title": "J. Pharm. Sci."
    },
    {
      "key": "ref46/cit46",
      "doi-asserted-by": "crossref",
      "first-page": "2310",
      "DOI": "10.1021/ci300245q",
      "volume": "52",
      "author": "Sushko I.",
      "year": "2012",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref47/cit47",
      "doi-asserted-by": "crossref",
      "first-page": "445",
      "DOI": "10.1177/026119290503300508",
      "volume": "33",
      "author": "Jaworska J.",
      "year": "2005",
      "journal-title": "Altern. Lab. Anim."
    },
    {
      "key": "ref48/cit48",
      "doi-asserted-by": "crossref",
      "first-page": "1990",
      "DOI": "10.1021/ci400213d",
      "volume": "53",
      "author": "Tetko I. V.",
      "year": "2013",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref49/cit49",
      "doi-asserted-by": "crossref",
      "first-page": "4",
      "DOI": "10.1186/1758-2946-5-4",
      "volume": "5",
      "author": "Oprisiu I.",
      "year": "2013",
      "journal-title": "J. Cheminform."
    },
    {
      "key": "ref50/cit50",
      "doi-asserted-by": "crossref",
      "first-page": "2837",
      "DOI": "10.1021/ci400482e",
      "volume": "53",
      "author": "Sheridan R. P.",
      "year": "2013",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref51/cit51",
      "doi-asserted-by": "crossref",
      "first-page": "34",
      "DOI": "10.1186/1758-2946-6-34",
      "volume": "6",
      "author": "Clark R. D.",
      "year": "2014",
      "journal-title": "J. Cheminf."
    },
    {
      "key": "ref52/cit52",
      "doi-asserted-by": "crossref",
      "first-page": "975",
      "DOI": "10.1021/ci3000198",
      "volume": "52",
      "author": "Brandmaier S.",
      "year": "2012",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref53/cit53",
      "doi-asserted-by": "crossref",
      "first-page": "1596",
      "DOI": "10.1021/ci5001168",
      "volume": "54",
      "author": "Norinder U.",
      "year": "2014",
      "journal-title": "J. Chem. Inf. Model."
    },
    {
      "key": "ref54/cit54",
      "doi-asserted-by": "crossref",
      "first-page": "203",
      "DOI": "10.1007/s10822-013-9639-5",
      "volume": "27",
      "author": "Wood D. J.",
      "year": "2013",
      "journal-title": "J. Comput.-Aided. Mol. Des."
    }
  ],
  "container-title": "Journal of Chemical Information and Modeling",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://pubs.acs.org/doi/pdf/10.1021/ci5005288",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        4,
        17
      ]
    ],
    "date-time": "2023-04-17T23:18:45Z",
    "timestamp": 1681773525000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://pubs.acs.org/doi/10.1021/ci5005288"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2014,
        12,
        9
      ]
    ]
  },
  "references-count": 54,
  "journal-issue": {
    "issue": "12",
    "published-print": {
      "date-parts": [
        [
          2014,
          12,
          22
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1021/ci5005288"
  ],
  "URL": "http://dx.doi.org/10.1021/ci5005288",
  "relation": {},
  "ISSN": [
    "1549-9596",
    "1549-960X"
  ],
  "subject": [],
  "container-title-short": "J. Chem. Inf. Model.",
  "published": {
    "date-parts": [
      [
        2014,
        12,
        9
      ]
    ]
  }
}