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    Chemistry

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    Also known as: Pixatimod [inn], Pg-545 free acid, 66qr34c83n, 1144617-49-1, Pg545, Pixatimod [who-dd]
    Molecular Formula
    C51H88O60S13
    Molecular Weight
    2078.1  g/mol
    InChI Key
    LNUFLCYMSVYYNW-ZPJMAFJPSA-N
    FDA UNII
    66QR34C83N
    Pixatimod
    Pixatimod is a synthetic sugar modified heparan sulfate mimetic and agonist of toll-like receptor 9 (TLR9), with potential immunostimulating, antineoplastic and anti-viral activities. Upon administration, pixatimod binds to and activates TLR9 expressed by dendritic cells (DCs) and B-cells. This initiates cytokine release from DCs and activates innate immune signaling pathways, and leads to the activation of natural killer (NK) cells to destroy tumor cells. The combination of pixatimod with certain checkpoint inhibitors may enhance the activation of cytotoxic T-lymphocytes to further kill tumor cells. In addition, pixatimod inhibits the cleavage of heparan sulfate from cell surface proteoglycan by heparanase (HPSE) and inhibits the infiltration of tumor-associated macrophages (TAMs). TLR9, a member of the TLR family, plays a fundamental role in pathogen recognition and activation of innate immunity.
    1 2D Structure

    Pixatimod

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-3,5-disulfooxy-6-(sulfooxymethyl)oxan-4-yl] hydrogen sulfate
    2.1.2 InChI
    InChI=1S/C51H88O60S13/c1-22(2)7-6-8-23(3)27-11-12-28-26-10-9-24-17-25(13-15-50(24,4)29(26)14-16-51(27,28)5)95-46-42(108-121(79,80)81)38(104-117(67,68)69)34(30(96-46)18-91-112(52,53)54)100-47-43(109-122(82,83)84)39(105-118(70,71)72)35(31(97-47)19-92-113(55,56)57)101-48-44(110-123(85,86)87)40(106-119(73,74)75)36(32(98-48)20-93-114(58,59)60)102-49-45(111-124(88,89)90)41(107-120(76,77)78)37(103-116(64,65)66)33(99-49)21-94-115(61,62)63/h22-49H,6-21H2,1-5H3,(H,52,53,54)(H,55,56,57)(H,58,59,60)(H,61,62,63)(H,64,65,66)(H,67,68,69)(H,70,71,72)(H,73,74,75)(H,76,77,78)(H,79,80,81)(H,82,83,84)(H,85,86,87)(H,88,89,90)/t23-,24+,25+,26+,27-,28+,29+,30-,31-,32-,33-,34-,35-,36-,37-,38+,39+,40+,41+,42-,43-,44-,45-,46-,47-,48-,49-,50+,51-/m1/s1
    2.1.3 InChI Key
    LNUFLCYMSVYYNW-ZPJMAFJPSA-N
    2.1.4 Canonical SMILES
    CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)OC5C(C(C(C(O5)COS(=O)(=O)O)OC6C(C(C(C(O6)COS(=O)(=O)O)OC7C(C(C(C(O7)COS(=O)(=O)O)OC8C(C(C(C(O8)COS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)C)C
    2.1.5 Isomeric SMILES
    C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COS(=O)(=O)O)O[C@@H]6[C@@H]([C@H]([C@@H]([C@H](O6)COS(=O)(=O)O)O[C@@H]7[C@@H]([C@H]([C@@H]([C@H](O7)COS(=O)(=O)O)O[C@@H]8[C@@H]([C@H]([C@@H]([C@H](O8)COS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)C)C
    2.2 Other Identifiers
    2.2.1 UNII
    66QR34C83N
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Pixatimod [inn]

    2. Pg-545 Free Acid

    3. 66qr34c83n

    4. 1144617-49-1

    5. Pg545

    6. Pixatimod [who-dd]

    7. Unii-66qr34c83n

    8. Gtpl9870

    9. Chembl2078841

    10. Compound 18 [pmid: 22458531]

    2.4 Create Date
    2012-08-06
    3 Chemical and Physical Properties
    Molecular Weight 2078.1 g/mol
    Molecular Formula C51H88O60S13
    XLogP3-4.2
    Hydrogen Bond Donor Count13
    Hydrogen Bond Acceptor Count60
    Rotatable Bond Count43
    Exact Mass2076.0204052 g/mol
    Monoisotopic Mass2076.0204052 g/mol
    Topological Polar Surface Area1010 Ų
    Heavy Atom Count124
    Formal Charge0
    Complexity5240
    Isotope Atom Count0
    Defined Atom Stereocenter Count29
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1

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