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    Technical details about Bufalin, learn more about the structure, uses, toxicity, action, side effects and more

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    Bufalin

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 465-21-4, 3-beta,14-dihydroxy-5-beta-bufa-20,22-dienolide, 3,14-dihydroxy-bufa-20,22-dienolide, U549s98qlw, 5-((3s,5r,8r,9s,10s,13r,14s,17r)-3,14-dihydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)-2h-pyran-2-one, Chebi:517248
    Molecular Formula
    C24H34O4
    Molecular Weight
    386.5  g/mol
    InChI Key
    QEEBRPGZBVVINN-BMPKRDENSA-N
    FDA UNII
    U549S98QLW
    Bufalin is an active ingredient and one of the glycosides in the traditional Chinese medicine ChanSu; it is also a bufadienolide toxin originally isolated from the venom of the Chinese toad Bufo gargarizans, with potential cardiotonic and antineoplastic activity. Although the mechanism of action of bufalin is still under investigation, this agent is a specific Na+/K+-ATPase inhibitor and can induce apoptosis in cancer cell lines through the activation of the transcription factor AP-1 via a mitogen activated protein kinase (MAPK) pathway.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
    2.1.2 InChI
    InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1
    2.1.3 InChI Key
    QEEBRPGZBVVINN-BMPKRDENSA-N
    2.1.4 Canonical SMILES
    CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=COC(=O)C=C5)O)C)O
    2.1.5 Isomeric SMILES
    C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@@]3(CC[C@@H]4C5=COC(=O)C=C5)O)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    U549S98QLW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bufalin, (3alpha,5beta)-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. 465-21-4

    2. 3-beta,14-dihydroxy-5-beta-bufa-20,22-dienolide

    3. 3,14-dihydroxy-bufa-20,22-dienolide

    4. U549s98qlw

    5. 5-((3s,5r,8r,9s,10s,13r,14s,17r)-3,14-dihydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)-2h-pyran-2-one

    6. Chebi:517248

    7. 3beta,14beta-dihydroxy-5beta-bufa-20,22-dienolide

    8. 5-[(3s,5r,8r,9s,10s,13r,14s,17r)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

    9. Unii-u549s98qlw

    10. Nsc-89595

    11. Ch'an Su

    12. Buf

    13. Nsc 89595

    14. Brn 5141601

    15. Bufalin [mi]

    16. (3beta,5beta)-3,14-dihydroxybufa-20,22-dienolide

    17. Bufalin [who-dd]

    18. Schembl165666

    19. Bufa-20,22-dienolide, 3,14-dihydroxy-, (3.beta.,5.beta.)-

    20. Chembl399680

    21. Bufa-20,22-dienolide, 3,14-dihydroxy-, (3b,5b)-

    22. Dtxsid90873563

    23. Amy40632

    24. Bufalin: Bufa-20,22-dienolide, 3,14-dihydroxy-, (3b,5b)-,

    25. Hy-n0877

    26. Zinc4215121

    27. Hsci1_000110

    28. Lmst01130001

    29. Mfcd30207876

    30. S7821

    31. Akos015965454

    32. Cs-3694

    33. Smp2_000290

    34. Ac-20197

    35. Ac-34068

    36. Bs-17080

    37. C16922

    38. 5beta-bufa-20,22-dienolide, 3beta,14-dihydroxy-

    39. Brd-k63606607-001-01-8

    40. Brd-k63606607-001-02-6

    41. Q18379323

    42. 5-beta-bufa-20,22-dienolide, 3-beta,14-dihydroxy-

    43. Bufa-20,22-dienolide, 3,14-dihydroxy-, (3beta,5beta)-

    44. Bufa-20,22-dienolide, 3,14-dihydroxy-, (3-beta,5-beta)-

    45. (3beta,5beta,10alpha,17alpha)-3,14-dihydroxybufa-20,22-dienolide

    2.4 Create Date
    2006-08-30
    3 Chemical and Physical Properties
    Molecular Weight 386.5 g/mol
    Molecular Formula C24H34O4
    XLogP33.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count1
    Exact Mass386.24570956 g/mol
    Monoisotopic Mass386.24570956 g/mol
    Topological Polar Surface Area66.8 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity741
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Cardiotonic Agents

    Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)