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Issue 1, 2014
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Matched molecular pairs derived by retrosynthetic fragmentation

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Matched molecular pairs (MMPs) are defined as pairs of compounds that only differ by a chemical change at a single site. MMPs have become popular in medicinal chemistry to support lead optimization, absorption, distribution, metabolism, excretion, and toxicity (ADMET) analysis, and other applications. Thus far, MMPs have been algorithmically defined and not on the basis of reaction information. This often limits the chemical interpretability and practical utility of MMPs. Therefore, we introduce synthetically accessible MMPs that are automatically generated by applying reaction rules following the retrosynthetic combinatorial analysis procedure (RECAP). A library of more than 92 000 RECAP-MMPs was generated from public domain compounds active against 435 different targets exclusively utilizing high-confidence activity data. This library is made freely available for use in medicinal chemistry.

Graphical abstract: Matched molecular pairs derived by retrosynthetic fragmentation

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Publication details

The article was received on 10 Sep 2013, accepted on 27 Oct 2013 and first published on 22 Nov 2013

Article type: Concise Article
DOI: 10.1039/C3MD00259D
Citation: Med. Chem. Commun., 2014,5, 64-67

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    Matched molecular pairs derived by retrosynthetic fragmentation

    A. de la Vega de León and J. Bajorath, Med. Chem. Commun., 2014, 5, 64
    DOI: 10.1039/C3MD00259D

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