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Bufalin

Bufalin

Synopsis, Chemistry

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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

Bufalin

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 Formula	C₂₄H₃₄O₄
Molecular Weight	386.5 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Exact Mass	386.24570956 g/mol
Monoisotopic Mass	386.24570956 g/mol
Topological Polar Surface Area	66.8 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	741
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.)