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    Chemistry

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    Also known as: 1051366-32-5, Pol6326, Cyclo(l-alanyl-l-cysteinyl-l-seryl-l-alanyl-d-prolyl-(2s)-2,4-diaminobutanoyl-l-arginyl-l-tyrosyl-l-cysteinyl-l-tyrosyl-l-glutaminyl-l-lysyl-d-prolyl-l-prolyl-l-tyrosyl-l-histidyl), cyclic (2->9)-disulfide, Balixafortide [inn], Balixafortide [usan], Balixafortide(pol6326)
    Molecular Formula
    C84H118N24O21S2
    Molecular Weight
    1864.1  g/mol
    InChI Key
    OYWQJZAVFWOOBF-WBMPNIIXSA-N
    Balixafortide
    Balixafortide is an orally bioavailable inhibitor of CXC chemokine receptor 4 (CXCR4) with receptor binding and hematopoietic stem cell-mobilization activities. Balixafortide binds to the chemokine receptor CXCR4, thereby preventing the binding of stromal derived factor-1 (SDF-1 or CXCL12) to the CXCR4 receptor and subsequent receptor activation. This may induce the mobilization of hematopoietic stem and progenitor cells from the bone marrow into blood. CXCR4, a chemokine receptor belonging to the G protein-coupled receptor (GPCR) gene family, plays an important role in chemotaxis and angiogenesis and is upregulated in several tumor cell types; CXCL12/CXCR4 interaction induces retention of hematopoietic cells in the bone marrow.
    1 2D Structure

    Balixafortide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[(1R,4S,7S,10S,16S,22R,25S,28S,31S,34R,37S,40S,43S,46R,52S,55S)-25-(4-aminobutyl)-43-(2-aminoethyl)-40-(3-carbamimidamidopropyl)-55-(hydroxymethyl)-10,31,37-tris[(4-hydroxyphenyl)methyl]-7-(1H-imidazol-5-ylmethyl)-4,52-dimethyl-3,8,11,17,23,26,29,32,35,38,39,42,45,51,54,57-hexadecaoxo-59,60-dithia-2,5,6,9,12,18,24,27,30,33,36,41,44,50,53,56-hexadecazapentacyclo[32.23.4.012,16.018,22.046,50]henhexacontan-28-yl]propanamide
    2.1.2 InChI
    InChI=1S/C84H118N24O21S2/c1-44-70(116)102-62-41-130-131-42-63(77(123)98-57(35-46-14-20-50(110)21-15-46)69(115)68(114)53(10-5-31-91-84(88)89)94-73(119)56(28-30-86)97-79(125)64-11-6-32-106(64)81(127)45(2)93-76(122)61(40-109)101-78(62)124)103-74(120)58(36-47-16-22-51(111)23-17-47)99-72(118)55(26-27-67(87)113)95-71(117)54(9-3-4-29-85)96-80(126)65-12-7-33-107(65)83(129)66-13-8-34-108(66)82(128)60(37-48-18-24-52(112)25-19-48)100-75(121)59(105-104-44)38-49-39-90-43-92-49/h14-25,39,43-45,53-66,104-105,109-112H,3-13,26-38,40-42,85-86H2,1-2H3,(H2,87,113)(H,90,92)(H,93,122)(H,94,119)(H,95,117)(H,96,126)(H,97,125)(H,98,123)(H,99,118)(H,100,121)(H,101,124)(H,102,116)(H,103,120)(H4,88,89,91)/t44-,45-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64+,65+,66-/m0/s1
    2.1.3 InChI Key
    OYWQJZAVFWOOBF-WBMPNIIXSA-N
    2.1.4 Canonical SMILES
    CC1C(=O)NC2CSSCC(C(=O)NC(C(=O)C(=O)C(NC(=O)C(NC(=O)C3CCCN3C(=O)C(NC(=O)C(NC2=O)CO)C)CCN)CCCNC(=N)N)CC4=CC=C(C=C4)O)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C5CCCN5C(=O)C6CCCN6C(=O)C(NC(=O)C(NN1)CC7=CN=CN7)CC8=CC=C(C=C8)O)CCCCN)CCC(=O)N)CC9=CC=C(C=C9)O
    2.1.5 Isomeric SMILES
    C[C@H]1C(=O)N[C@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]3CCCN3C(=O)[C@@H](NC(=O)[C@@H](NC2=O)CO)C)CCN)CCCNC(=N)N)CC4=CC=C(C=C4)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]5CCCN5C(=O)[C@@H]6CCCN6C(=O)[C@@H](NC(=O)[C@@H](NN1)CC7=CN=CN7)CC8=CC=C(C=C8)O)CCCCN)CCC(=O)N)CC9=CC=C(C=C9)O
    2.2 Synonyms
    2.2.1 Depositor-Supplied Synonyms

    1. 1051366-32-5

    2. Pol6326

    3. Cyclo(l-alanyl-l-cysteinyl-l-seryl-l-alanyl-d-prolyl-(2s)-2,4-diaminobutanoyl-l-arginyl-l-tyrosyl-l-cysteinyl-l-tyrosyl-l-glutaminyl-l-lysyl-d-prolyl-l-prolyl-l-tyrosyl-l-histidyl), Cyclic (2->9)-disulfide

    4. Balixafortide [inn]

    5. Balixafortide [usan]

    6. Balixafortide(pol6326)

    7. Balixafortide (pol6326)

    8. Unii-prc974m49b

    9. Prc974m49b

    10. Gtpl11587

    11. Pol 6326

    12. Who 9915

    13. S9725

    14. Ala-cys-ser-ala-pro-arg-tyr-cys-tyr-gln-lys-pro-pro-tyr-his Cyclic (2->9)-disulfide

    2.3 Create Date
    2019-07-22
    3 Chemical and Physical Properties
    Molecular Weight 1864.1 g/mol
    Molecular Formula C84H118N24O21S2
    XLogP3-3.5
    Hydrogen Bond Donor Count24
    Hydrogen Bond Acceptor Count29
    Rotatable Bond Count23
    Exact Mass1862.83447922 g/mol
    Monoisotopic Mass1862.83447922 g/mol
    Topological Polar Surface Area757 Ų
    Heavy Atom Count131
    Formal Charge0
    Complexity3970
    Isotope Atom Count0
    Defined Atom Stereocenter Count16
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of breast cancer

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