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    Uproleselan

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    2D Structure
    Also known as: Uproleselan [usan], Gmi-1271, Gmi-1271 free acid, Pe952anf83, 1983970-12-2, Uproleselan [inn]
    Molecular Formula
    C60H109N3O27
    Molecular Weight
    1304.5  g/mol
    InChI Key
    LYSYOXNOOPBOSC-NGSKMYNLSA-N
    FDA UNII
    PE952ANF83
    Uproleselan is a synthetic, glycomimetic molecule and E-selectin (CD62E) antagonist, with potential anti-thrombotic, antineoplastic and chemopotentiating activities. Upon administration, uproleselan binds to E-selectin expressed on endothelial cells and prevents their interaction with selectin-E ligand-expressing cancer cells. This may prevent tumor cell activation, migration and metastasis. GMI-1271 also interferes with the binding of selectin E-expressing vascular endothelial cells to selectin-E ligand-expressing monocytes and neutrophils, thereby disrupting their activation. Consequently, this inhibits both the activation of the coagulation cascade and thrombus formation. This agent also prevents both leukocyte activation and inflammation. E-selectin is a cell adhesion molecule involved in cell rolling, signaling and chemotaxis; it also plays a crucial role in inflammatory processes and cancer.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-[(2R,3R,4R,5R,6R)-3-acetamido-2-[(1R,2R,3S,5R)-3-ethyl-5-[2-[3-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]ethylcarbamoyl]-2-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxycyclohexyl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-cyclohexylpropanoic acid
    2.1.2 InChI
    InChI=1S/C60H109N3O27/c1-5-44-38-45(39-46(55(44)90-60-54(70)53(69)51(67)41(2)86-60)88-59-50(63-42(3)65)56(52(68)48(40-64)89-59)87-47(58(72)73)37-43-9-7-6-8-10-43)57(71)62-13-12-61-49(66)11-14-75-17-18-77-21-22-79-25-26-81-29-30-83-33-34-85-36-35-84-32-31-82-28-27-80-24-23-78-20-19-76-16-15-74-4/h41,43-48,50-56,59-60,64,67-70H,5-40H2,1-4H3,(H,61,66)(H,62,71)(H,63,65)(H,72,73)/t41-,44-,45+,46+,47-,48+,50+,51+,52-,53+,54-,55+,56+,59+,60-/m0/s1
    2.1.3 InChI Key
    LYSYOXNOOPBOSC-NGSKMYNLSA-N
    2.1.4 Canonical SMILES
    CCC1CC(CC(C1OC2C(C(C(C(O2)C)O)O)O)OC3C(C(C(C(O3)CO)O)OC(CC4CCCCC4)C(=O)O)NC(=O)C)C(=O)NCCNC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOC
    2.1.5 Isomeric SMILES
    CC[C@H]1C[C@H](C[C@H]([C@@H]1O[C@H]2[C@H]([C@@H]([C@@H]([C@@H](O2)C)O)O)O)O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O[C@@H](CC4CCCCC4)C(=O)O)NC(=O)C)C(=O)NCCNC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOC
    2.2 Other Identifiers
    2.2.1 UNII
    PE952ANF83
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2s)-2-(((2r,3r,4r,5r,6r)-3-acetamido-2-(((1r,2r,3s,5r)-5-((2-(4,7,10,13,16,19,22,25,28,31,34,37-dodecaoxaoctatriacontanamido)ethyl)carbamoyl)-3-ethyl-2-(alpha-l-galactopyranosyloxy)cyclohexyl)oxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl)oxy)-3-cyc

    2. Abi-701

    3. Abi701

    4. Gmi-1271

    5. Gmi-1271 Free Acid

    6. Gmi-1271 Sodium

    7. Gmi-1687

    8. Sodium (2s)-2-(((2r,3r,4r,5r,6r)-3-acetamido-2-(((1r,2r,3s,5r)-5-((2-(4,7,10,13,16,19,22,25,28,31,34,37-dodecaoxaoctatriacontanamido)ethyl)carbamoyl)-3-ethyl-2-(alpha-l-galactopyranosyloxy)cyclohexyl)oxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl)oxy

    9. Uproleselan Sodium

    2.3.2 Depositor-Supplied Synonyms

    1. Uproleselan [usan]

    2. Gmi-1271

    3. Gmi-1271 Free Acid

    4. Pe952anf83

    5. 1983970-12-2

    6. Uproleselan [inn]

    7. Uproleselan (usan/inn)

    8. Unii-pe952anf83

    9. Uproleselan [who-dd]

    10. Chembl3989971

    11. Gtpl11995

    12. Gmi1271

    13. Db14829

    14. D11332

    15. (2s)-2-(((2r,3r,4r,5r,6r)-3-acetamido-2-(((1r,2r,3s,5r)-5-((2-(4,7,10,13,16,19,22,25,28,31,34,37-dodecaoxaoctatriacontanamido)ethyl)carbamoyl)-3-ethyl-2-(alpha-l-galactopyranosyloxy)cyclohexyl)oxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl)oxy)-3-cyclohexylpropanoic Acid

    16. 4,7,10,13,16,19,22,25,28,31,34,37-dodecaoxaoctatriacontanamide, N-(2-((((1r,3r,4r,5s)-3-((2-(acetylamino)-3-o-((1s)-1-carboxy-2-cyclohexylethyl)-2-deoxy-bata-d-galactopyranosyl)oxy)-4-((6-deoxy-alpha-l-galactopyranosyl)oxy)-5-ethylcyclohexyl)carbonyl)amino)ethyl)-

    2.4 Create Date
    2013-07-15
    3 Chemical and Physical Properties
    Molecular Weight 1304.5 g/mol
    Molecular Formula C60H109N3O27
    XLogP3-2
    Hydrogen Bond Donor Count9
    Hydrogen Bond Acceptor Count27
    Rotatable Bond Count52
    Exact Mass1303.72484521 g/mol
    Monoisotopic Mass1303.72484521 g/mol
    Topological Polar Surface Area383 Ų
    Heavy Atom Count90
    Formal Charge0
    Complexity1870
    Isotope Atom Count0
    Defined Atom Stereocenter Count15
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1