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    Rintatolimod

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    DIGITAL CONTENT

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    2D Structure
    Also known as: 38640-92-5, [(2r,3s,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate;[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-oxo-1h-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate;[(2r,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate, Schembl27306, Dtxsid50191952
    Molecular Formula
    C28H40N9O25P3
    Molecular Weight
    995.6  g/mol
    InChI Key
    KNUXHTWUIVMBBY-JRJYXWDASA-N
    Rintatolimod is a synthetic derivative of inosinic acid with antiretroviral and immunomodulatory properties. Atvogen acts through a number of pathways to stimulate intracellular antiviral activity of the immune system: it stimulates interferon production; activates the oligoadenylate synthase-RNase L pathway; stimulates natural killer cell activity; and acts as a non-mitogenic stimulator of the immune system. This agent also inhibits replication of human immunodeficiency virus (HIV) in vitro. (NCI04)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate;[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate;[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
    2.1.2 InChI
    InChI=1S/C10H13N4O8P.C9H14N3O8P.C9H13N2O9P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17;10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18;12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20);1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18);1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,10-;2*4-,6-,7-,8-/m111/s1
    2.1.3 InChI Key
    KNUXHTWUIVMBBY-JRJYXWDASA-N
    2.1.4 Canonical SMILES
    C1=CN(C(=O)N=C1N)C2C(C(C(O2)COP(=O)(O)O)O)O.C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)O)O)O.C1=NC2=C(C(=O)N1)N=CN2C3C(C(C(O3)COP(=O)(O)O)O)O
    2.1.5 Isomeric SMILES
    C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O.C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O.C1=NC2=C(C(=O)N1)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. (ri(n).r(c(12)u)n)

    2. Ampligen

    3. Mismatched Double-stranded Rna

    4. Poly(i)-poly(c12u)

    5. Poly(i).poly(c12,u)

    6. Poly(inosinic Acid) Poly(cytidylic(12), Uridylic)acid

    2.2.2 Depositor-Supplied Synonyms

    1. 38640-92-5

    2. [(2r,3s,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl Dihydrogen Phosphate;[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-oxo-1h-purin-9-yl)oxolan-2-yl]methyl Dihydrogen Phosphate;[(2r,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl Dihydrogen Phosphate

    3. Schembl27306

    4. Dtxsid50191952

    2.3 Create Date
    2019-01-15
    3 Chemical and Physical Properties
    Molecular Weight 995.6 g/mol
    Molecular Formula C28H40N9O25P3
    Hydrogen Bond Donor Count15
    Hydrogen Bond Acceptor Count27
    Rotatable Bond Count12
    Exact Mass995.13481879 g/mol
    Monoisotopic Mass995.13481879 g/mol
    Topological Polar Surface Area517 Ų
    Heavy Atom Count65
    Formal Charge0
    Complexity1600
    Isotope Atom Count0
    Defined Atom Stereocenter Count12
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antiviral Agents

    Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)