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    Chemistry

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    Also known as: Tulmimetostat [inn], Ouq4n85z0b, 1,3-benzodioxole-5-carboxamide, 7-chloro-n-((1,2-dihydro-6-methyl-4-(methylthio)-2-oxo-3-pyridinyl)methyl)-2-(trans-4-(3-methoxy-1-azetidinyl)cyclohexyl)-2,4-dimethyl-, (2r)-, 2567686-02-4, Unii-ouq4n85z0b, Schembl22915712
    Molecular Formula
    C28H36ClN3O5S
    Molecular Weight
    562.1  g/mol
    InChI Key
    CAAWBLRXQXMGHV-WOLMIXIISA-N
    FDA UNII
    OUQ4N85Z0B
    Tulmimetostat
    Tulmimetostat is an orally available selective inhibitor of the histone lysine methyltransferase (HMT) enhancer of zeste homolog 2 (EZH2), with potential antineoplastic activity. Upon oral administration, tulmimetostat selectively targets, binds to and inhibits the activity of EZH2. Inhibition of EZH2 specifically prevents the methylation of histone H3 on lysine 27 (H3K27). This decrease in histone methylation alters gene expression patterns associated with cancer pathways and results in decreased proliferation of EZH2-expressing cancer cells. EZH2, an HMT class enzyme and the catalytic subunit of the polycomb repressive complex 2 (PRC2), is overexpressed or mutated in a variety of cancer cells and plays a key role in tumor cell proliferation; its expression is correlated with tumor initiation, progression, stem cell self-renewal, migration and angiogenesis.
    1 2D Structure

    Tulmimetostat

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R)-7-chloro-2-[4-(3-methoxyazetidin-1-yl)cyclohexyl]-2,4-dimethyl-N-[(6-methyl-4-methylsulfanyl-2-oxo-1H-pyridin-3-yl)methyl]-1,3-benzodioxole-5-carboxamide
    2.1.2 InChI
    InChI=1S/C28H36ClN3O5S/c1-15-10-23(38-5)21(27(34)31-15)12-30-26(33)20-11-22(29)25-24(16(20)2)36-28(3,37-25)17-6-8-18(9-7-17)32-13-19(14-32)35-4/h10-11,17-19H,6-9,12-14H2,1-5H3,(H,30,33)(H,31,34)/t17?,18?,28-/m1/s1
    2.1.3 InChI Key
    CAAWBLRXQXMGHV-WOLMIXIISA-N
    2.1.4 Canonical SMILES
    CC1=CC(=C(C(=O)N1)CNC(=O)C2=CC(=C3C(=C2C)OC(O3)(C)C4CCC(CC4)N5CC(C5)OC)Cl)SC
    2.1.5 Isomeric SMILES
    CC1=CC(=C(C(=O)N1)CNC(=O)C2=CC(=C3C(=C2C)O[C@@](O3)(C)C4CCC(CC4)N5CC(C5)OC)Cl)SC
    2.2 Other Identifiers
    2.2.1 UNII
    OUQ4N85Z0B
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Tulmimetostat [inn]

    2. Ouq4n85z0b

    3. 1,3-benzodioxole-5-carboxamide, 7-chloro-n-((1,2-dihydro-6-methyl-4-(methylthio)-2-oxo-3-pyridinyl)methyl)-2-(trans-4-(3-methoxy-1-azetidinyl)cyclohexyl)-2,4-dimethyl-, (2r)-

    4. 2567686-02-4

    5. Unii-ouq4n85z0b

    6. Schembl22915712

    7. Schembl22915728

    8. Schembl22922941

    9. Cpi0209

    10. Cpi-0209 [who-dd]

    11. Cpi-0209

    12. Hy-145602

    13. Cs-0376691

    2.4 Create Date
    2021-02-21
    3 Chemical and Physical Properties
    Molecular Weight 562.1 g/mol
    Molecular Formula C28H36ClN3O5S
    XLogP34.5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count7
    Exact Mass561.2064201 g/mol
    Monoisotopic Mass561.2064201 g/mol
    Topological Polar Surface Area114 Ų
    Heavy Atom Count38
    Formal Charge0
    Complexity993
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1

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