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    Fosmanogepix

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: Apx001, 2091769-17-2, Fosmanogepix [inn], Fosmanogepix [usan], Apx-001, 1xq871489p
    Molecular Formula
    C22H21N4O6P
    Molecular Weight
    468.4  g/mol
    InChI Key
    JQONJQKKVAHONF-UHFFFAOYSA-N
    FDA UNII
    1XQ871489P
    Fosmanogepix is an orally available small molecule inhibitor of the Gwt1 fungal enzyme with potential antifungal activity. Upon administration, fosmanogepix, a N-phosphonooxymethyl prodrug, is rapidly and completely metabolized by systemic alkaline phosphatases to its active moiety, APX001A (E1210). The active prodrug targets Gwt1, a highly conserved inositol acylase which catalyzes an essential step in the glycosylphosphatidylinositol (GPI)-anchor biosynthesis pathway. Inhibition of Gwt1 prevents localization of cell wall mannoproteins, which compromises cell wall integrity, biofilm formation, germ tube formation, and fungal growth.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [2-amino-3-[3-[[4-(pyridin-2-yloxymethyl)phenyl]methyl]-1,2-oxazol-5-yl]pyridin-1-ium-1-yl]methyl hydrogen phosphate
    2.1.2 InChI
    InChI=1S/C22H21N4O6P/c23-22-19(4-3-11-26(22)15-31-33(27,28)29)20-13-18(25-32-20)12-16-6-8-17(9-7-16)14-30-21-5-1-2-10-24-21/h1-11,13,23H,12,14-15H2,(H2,27,28,29)
    2.1.3 InChI Key
    JQONJQKKVAHONF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=NC(=C1)OCC2=CC=C(C=C2)CC3=NOC(=C3)C4=C([N+](=CC=C4)COP(=O)(O)[O-])N
    2.2 Other Identifiers
    2.2.1 UNII
    1XQ871489P
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Apx001

    2. 2091769-17-2

    3. Fosmanogepix [inn]

    4. Fosmanogepix [usan]

    5. Apx-001

    6. 1xq871489p

    7. E1211

    8. (2-amino-3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-1-ium-1-yl)methyl Hydrogen Phosphate

    9. Pyridinium, 2-amino-1-((phosphonooxy)methyl)-3-(3-((4-((2-pyridinyloxy)methyl)phenyl)methyl)-5-isoxazolyl)-, Inner Salt

    10. Fosmanogepix (usan/inn)

    11. Chembl4297591

    12. Schembl22749842

    13. Unii-1xq871489p

    14. Ex-a5184

    15. Who 10818

    16. Db15183

    17. 1169701-00-1

    18. D11694

    19. (12-amino-6-oxa-1(3),7(2)-dipyridina-2(5,3)-(1,2)oxazola- 4(1,4)-benzenaheptaphan-11-ium-11-yl)methyl Hydrogen Phosphate

    20. (12-amino-6-oxa-1(3),7(2)-dipyridina-2(5,3)-(1,2)oxazola-4(1,4)-benzenaheptaphan-11-ium-11-yl)methyl Hydrogen Phosphate

    21. (2-amino-3-(3-((4-(2-pyridyloxymethyl)phenyl)methyl)isoxazol-5-yl)pyridin-1-ium-1-yl)methyl Hydrogen Phosphate

    22. [2-amino-3-[3-[[4-(pyridin-2-yloxymethyl)phenyl]methyl]-1,2-oxazol-5-yl]pyridin-1-ium-1-yl]methyl Hydrogen Phosphate

    2.4 Create Date
    2009-07-27
    3 Chemical and Physical Properties
    Molecular Weight 468.4 g/mol
    Molecular Formula C22H21N4O6P
    XLogP31.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count9
    Exact Mass468.11987140 g/mol
    Monoisotopic Mass468.11987140 g/mol
    Topological Polar Surface Area148 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity644
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1