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    Beloranib

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    DIGITAL CONTENT

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    2D Structure
    Also known as: 251111-30-5, Beloranib [inn], Zgn-433, Zgn-440, Ckd-732, Zgn 440
    Molecular Formula
    C29H41NO6
    Molecular Weight
    499.6  g/mol
    InChI Key
    ZEZFKUBILQRZCK-MJSCXXSSSA-N
    FDA UNII
    FI471K8BU6
    Beloranib is a fumagillin analogue and inhibitor of methionine aminopeptidase 2 (METAP2), with potential antiangiogenic and anti-obesity activity. As an irreversible inhibitor, beloranib blocks METAP2's functions, which include both protecting eukaryotic initiation factor 2 from inhibitory phosphorylation during translation, and by removing the amino-terminal methionine residue from nascent protein permitting the conversion of an inactive or non-functional protein to an active one. As a result, this agent prevents endothelial cell growth and inhibits tumor angiogenesis. In addition, METAP2 inhibition also down-regulates ERK1/2 signaling pathway, which is usually overactive in the fat tissues of obese people. Therefore, at a much lower dose, beloranib can induce liver fat utilization and reduce cholesterol and fatty acid synthesis. METAP2, a member of the dimetallohydrolase family, plays an important role during angiogenesis and is over-expressed in various cancers.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] (E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]prop-2-enoate
    2.1.2 InChI
    InChI=1S/C29H41NO6/c1-20(2)7-13-24-28(3,36-24)27-26(32-6)23(15-16-29(27)19-34-29)35-25(31)14-10-21-8-11-22(12-9-21)33-18-17-30(4)5/h7-12,14,23-24,26-27H,13,15-19H2,1-6H3/b14-10+/t23-,24-,26-,27-,28+,29+/m1/s1
    2.1.3 InChI Key
    ZEZFKUBILQRZCK-MJSCXXSSSA-N
    2.1.4 Canonical SMILES
    CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)OC(=O)C=CC4=CC=C(C=C4)OCCN(C)C)OC)C
    2.1.5 Isomeric SMILES
    CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@]23CO3)OC(=O)/C=C/C4=CC=C(C=C4)OCCN(C)C)OC)C
    2.2 Other Identifiers
    2.2.1 UNII
    FI471K8BU6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (3r,4s,5s,6r)-5-methoxy-4-((2r,3r)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl)-1-oxaspiro(2.5)oct-6-yl (2e)-3-(4-(2-(dimethylamino)ethoxy)phenyl)acrylate

    2. Ckd-732

    3. Ckd732

    4. O-(4-dimethylaminoethoxycinnamoyl)fumagillol

    2.3.2 Depositor-Supplied Synonyms

    1. 251111-30-5

    2. Beloranib [inn]

    3. Zgn-433

    4. Zgn-440

    5. Ckd-732

    6. Zgn 440

    7. O-[4-(2-dimethylaminoethoxy)-trans-cinnamoyl]fumagillol

    8. Fi471k8bu6

    9. (3r,4s,5s,6r)-5-methoxy-4-((2r,3r)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro(2.5)octan-6-yl (2e)-3-(4-(2-(dimethylamino)ethoxy)phenyl)prop-2-enoate

    10. O-(4-(2-dimethylaminoethoxy)-trans-cinnamoyl)fumagillol

    11. 609845-93-4

    12. Unii-fi471k8bu6

    13. Zgn 433

    14. [(3r,4s,5s,6r)-5-methoxy-4-[(2r,3r)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] (e)-3-[4-[2-(dimethylamino)ethoxy]phenyl]prop-2-enoate

    15. Zgn-440(beloranib)

    16. O-(4-dimethylaminoethoxycinnamoyl)fumagillol

    17. Beloranib [who-dd]

    18. Gtpl8445

    19. Us9682965, Compound A

    20. Chembl4297504

    21. Schembl14648763

    22. Dtxsid40179800

    23. Bdbm148430

    24. Zgn-440;cdk-732

    25. Zinc3982162

    26. Db12671

    27. (3r,4s,5s,6r)-5-methoxy-4-((2r,3r)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl)-1-oxaspiro(2.5)oct-6-yl (2e)-3-(4-(2-(dimethylamino)ethoxy)phenyl)acrylate

    28. Hy-14811

    29. Cs-0003572

    30. A13870

    31. Q4884554

    32. [(3r,4s,5s,6r)-5-methoxy-4-[(2r,3r)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] (e)-3-[4-(2-dimethylaminoethoxy)phenyl]prop-2-enoate

    33. 3-[4-[2-(dimethylamino)ethoxy]phenyl]acrylic Acid (3r)-4beta-[(2r,3r)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-5alpha-methoxy-1-oxaspiro[2.5]octane-6alpha-yl Ester

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 499.6 g/mol
    Molecular Formula C29H41NO6
    XLogP34.4
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count12
    Exact Mass499.29338803 g/mol
    Monoisotopic Mass499.29338803 g/mol
    Topological Polar Surface Area73.1 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity815
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Angiogenesis Inhibitors

    Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)

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