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    TP-1287

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: Tp-1287, 2044686-42-0, 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5-hydroxy-8-((3s,4r)-3-hydroxy-1-methyl-4-piperidinyl)-7-(phosphonooxy)-, Alvocidib phosphate, Unii-7mpp85iij3, Alvocidib prodrug tp-1287
    Molecular Formula
    C21H21ClNO8P
    Molecular Weight
    481.8  g/mol
    InChI Key
    YRNFLVUMZIRYKY-BLLLJJGKSA-N
    FDA UNII
    7MPP85IIJ3
    Alvocidib Prodrug TP-1287 is an orally bioavailable, highly soluble phosphate prodrug of alvocidib, a potent inhibitor of cyclin-dependent kinase-9 (CDK9), with potential antineoplastic activity. Upon administration of the phosphate prodrug TP-1287, the prodrug is enzymatically cleaved at the tumor site and the active moiety alvocidib is released. Alvocidib targets and binds to CDK9, thereby reducing the expression of CDK9 target genes such as the anti-apoptotic protein MCL-1, and inducing G1 cell cycle arrest and apoptosis in CDK9-overexpressing cancer cells.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [2-(2-chlorophenyl)-5-hydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-4-oxochromen-7-yl] dihydrogen phosphate
    2.1.2 InChI
    InChI=1S/C21H21ClNO8P/c1-23-7-6-12(16(26)10-23)19-18(31-32(27,28)29)9-15(25)20-14(24)8-17(30-21(19)20)11-4-2-3-5-13(11)22/h2-5,8-9,12,16,25-26H,6-7,10H2,1H3,(H2,27,28,29)/t12-,16+/m0/s1
    2.1.3 InChI Key
    YRNFLVUMZIRYKY-BLLLJJGKSA-N
    2.1.4 Canonical SMILES
    CN1CCC(C(C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)OP(=O)(O)O
    2.1.5 Isomeric SMILES
    CN1CC[C@@H]([C@@H](C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)OP(=O)(O)O
    2.2 Other Identifiers
    2.2.1 UNII
    7MPP85IIJ3
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Tp-1287

    2. 2044686-42-0

    3. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5-hydroxy-8-((3s,4r)-3-hydroxy-1-methyl-4-piperidinyl)-7-(phosphonooxy)-

    4. Alvocidib Phosphate

    5. Unii-7mpp85iij3

    6. Alvocidib Prodrug Tp-1287

    7. Chembl4594423

    8. Schembl18251861

    9. Tp-1287 [who-dd]

    10. Bdbm50553482

    11. Tp1287

    2.4 Create Date
    2017-02-18
    3 Chemical and Physical Properties
    Molecular Weight 481.8 g/mol
    Molecular Formula C21H21ClNO8P
    XLogP3-0.3
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count4
    Exact Mass481.0693313 g/mol
    Monoisotopic Mass481.0693313 g/mol
    Topological Polar Surface Area137 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity790
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1