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    Xevinapant

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    DIGITAL CONTENT

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    2D Structure
    Also known as: 1071992-99-8, At-406, Debio-1143, N65wc8pxdd, Sm-406, Unii-n65wc8pxdd
    Molecular Formula
    C32H43N5O4
    Molecular Weight
    561.7  g/mol
    InChI Key
    LSXUTRRVVSPWDZ-MKKUMYSQSA-N
    FDA UNII
    N65WC8PXDD
    Xevinapant is an orally available mimetic of the natural second mitochondrial-derived activator of caspases (Smac) and inhibitor of Inhibitor of Apoptosis Proteins (IAPs), with potential immunomodulating, apoptotic-inducing, chemo-radio-sensitizing and antineoplastic activities. Upon oral administration,xevinapant targets and binds to the Smac binding groove on IAPs, including the direct caspase inhibitor X chromosome-linked IAP (XIAP), and the cellular IAPs 1 (c-IAP1) and 2 (c-IAP2). This inhibits the activities of these IAPs and promotes the induction of apoptosis. Additionally, as xevinapant inhibits the activity of IAPs, it may work synergistically with cytotoxic drugs and/or radiation to overcome tumor cell resistance to apoptosis. As IAPs regulate nuclear factor-kappa B (NFkB) signaling pathways, which drives the expression of genes involved in immune and inflammatory responses, xevinapant may enhance anti-tumor immune responses when administered with certain immunomodulating agents, such as immune checkpoint inhibitors. IAPs are overexpressed by many cancer cell types and suppress both intrinsic and extrinsic apoptosis by binding to and inhibiting active caspases via their baculoviral lAP repeat (BIR) domains. They contribute to chemo-radio-resistance of cancer cells to certain cytotoxic agents and radiation, promote tumor cell survival and are associated with poor prognosis in certain types of cancer. SMAC, a pro-apoptotic mitochondrial protein, is an endogenous inhibitor of the IAPs family of cellular proteins.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (5S,8S,10aR)-N-benzhydryl-5-[[(2S)-2-(methylamino)propanoyl]amino]-3-(3-methylbutanoyl)-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
    2.1.2 InChI
    InChI=1S/C32H43N5O4/c1-21(2)19-28(38)36-18-17-25-15-16-27(37(25)32(41)26(20-36)34-30(39)22(3)33-4)31(40)35-29(23-11-7-5-8-12-23)24-13-9-6-10-14-24/h5-14,21-22,25-27,29,33H,15-20H2,1-4H3,(H,34,39)(H,35,40)/t22-,25+,26-,27-/m0/s1
    2.1.3 InChI Key
    LSXUTRRVVSPWDZ-MKKUMYSQSA-N
    2.1.4 Canonical SMILES
    CC(C)CC(=O)N1CCC2CCC(N2C(=O)C(C1)NC(=O)C(C)NC)C(=O)NC(C3=CC=CC=C3)C4=CC=CC=C4
    2.1.5 Isomeric SMILES
    C[C@@H](C(=O)N[C@H]1CN(CC[C@H]2CC[C@H](N2C1=O)C(=O)NC(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)CC(C)C)NC
    2.2 Other Identifiers
    2.2.1 UNII
    N65WC8PXDD
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. At 406

    2. At-406

    3. At406 Cpd

    4. Debio1143

    5. N-benzhydryl-5-(2-(methylamino)propanamido)-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo(1,2-a)(1,5)diazocine-8-carboxamide

    6. Sm 406

    7. Sm-406

    8. Sm406 Cpd

    2.3.2 Depositor-Supplied Synonyms

    1. 1071992-99-8

    2. At-406

    3. Debio-1143

    4. N65wc8pxdd

    5. Sm-406

    6. Unii-n65wc8pxdd

    7. At406

    8. (5s,8s,10ar)-n-benzhydryl-5-((s)-2-(methylamino)propanamido)-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide

    9. At 406

    10. Debio 1143

    11. Sm 406

    12. Xevinapant [inn]

    13. Chembl2158051

    14. Iap Inhibitor At-406

    15. Debio-1143 (at-406)

    16. At-406 (sm-406)

    17. 1071992-99-8 (free Base)

    18. At-406(at406)

    19. D-1143

    20. (5s,8s,10ar)-n-benzhydryl-5-[[(2s)-2-(methylamino)propanoyl]amino]-3-(3-methylbutanoyl)-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide

    21. Qcr-136

    22. (5s,8s,10ar)-n-(diphenylmethyl)-5-[(n-methyl-l-alanyl)amino]-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide

    23. At406 (sm-406)

    24. Debio1143

    25. Xevinapant [who-dd]

    26. Gtpl7729

    27. Schembl2724374

    28. Dtxsid50648496

    29. Ex-a104

    30. Bcp04668

    31. Bdbm50393505

    32. Mfcd22124467

    33. Nsc764757

    34. S2754

    35. Zinc43208643

    36. Ccg-270056

    37. Cs-0962

    38. Nsc-764757

    39. Ncgc00346675-01

    40. Ncgc00346675-03

    41. Ac-30282

    42. As-56453

    43. Hy-15454

    44. D 1143

    45. At406 (sm-406, Arry-334543)

    46. J-501625

    47. Q27074566

    48. 1071992-99-8, 1071992-57-8 (hcl)

    49. (5s,8s,10ar)-n-(diphenylmethyl)decahydro-5-(((2s)-2-(methylamino)-1-oxopropyl)amino)-3-(3-methyl-1-oxobutyl)-6-oxopyrrolo(1,2-a)(1,5)diazocine-8-carboxamide

    50. (5s,8s,10ar)-n-(diphenylmethyl)decahydro-5-[[(2s)-2-(methylamino)-1-oxopropyl]amino]-3-(3-methyl-1-oxobutyl)-6-oxopyrrolo[1,2-a][1,5 ]diazocine-8-carboxamide

    51. Pyrrolo(1,2-a)(1,5)diazocine-8-carboxamide, N-(diphenylmethyl)decahydro-5-(((2s)-2-(methylamino)-1-oxopropyl)amino)-3-(3-methyl-1-oxobutyl)-6-oxo-, (5s,8s,10ar)-

    2.4 Create Date
    2008-11-10
    3 Chemical and Physical Properties
    Molecular Weight 561.7 g/mol
    Molecular Formula C32H43N5O4
    XLogP33.1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count9
    Exact Mass561.33150487 g/mol
    Monoisotopic Mass561.33150487 g/mol
    Topological Polar Surface Area111 Ų
    Heavy Atom Count41
    Formal Charge0
    Complexity896
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1