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Chemistry

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Also known as: Proscillaridin-a, Caradrin, Caradrine, Nsc7521, Cardiovite, Proscillan
Molecular Formula
C30H42O8
Molecular Weight
530.6  g/mol
InChI Key
MYEJFUXQJGHEQK-OWBILYANSA-N

Proscillaridin
A cardiotonic glycoside isolated from Scilla maritima var. alba (Squill).
1 2D Structure

Proscillaridin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-[(3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
2.1.2 InChI
InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16?,19-,20+,21-,22+,24?,25?,26?,27?,28-,29+,30-/m0/s1
2.1.3 InChI Key
MYEJFUXQJGHEQK-OWBILYANSA-N
2.1.4 Canonical SMILES
CC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3=C2)O)C6=COC(=O)C=C6)C)C)O)O)O
2.1.5 Isomeric SMILES
CC1C(C(C(C(O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CCC3=C2)O)C6=COC(=O)C=C6)C)C)O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Caradrin

2. Desglucotransvaaline

3. Digitalysat

4. Proscillaridin

5. Proscillaridine

6. Rhamnoside, Scillarenin

7. Sandoscill

8. Scillarenin Rhamnoside

9. Scillase

10. Talusin

2.2.2 Depositor-Supplied Synonyms

1. Proscillaridin-a

2. Caradrin

3. Caradrine

4. Nsc7521

5. Cardiovite

6. Proscillan

7. Proscillaridine

8. Proslladin

9. Sandoscill

10. Scillacrist

11. Cardion

12. Carmazon

13. Coratol

14. Procardin

15. Procilan

16. Prostosin

17. Proszin

18. Protasin

19. Solestril

20. Stellarid

21. Talusin

22. Tradenal

23. Urgilan

24. Wirnesin

25. Simeon

26. Herzo Proscillan

27. Purosin-tc

28. 466-06-8

29. Transvaalin, Degluco-

30. 5-[(3s,8r,9s,10r,13r,14s,17r)-14-hydroxy-10,13-dimethyl-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

31. Psc-801

32. Desglucotransvaaline

33. A-32686

34. Scillarenin 3.beta.-rhamnoside

35. Scillarenin, 3.alpha.-l-rhamnopyranoside

36. Rhamnopyranoside, .alpha.-l-

37. Schembl1649544

38. Chembl1977418

39. Hbl0000188

40. Nci60_041645

41. P8334

42. 14-hydroxy-3.beta.-(rhamnosyloxy)bufa-4,22-trienolide

43. Desgluco-transvaalin3.beta.,20,22-trienolide 3-rhamnoside

44. (3beta)-3-[(6-deoxyhexopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide

45. [(6-deoxy-.alpha.-l-mannopyranosyl)oxy]-14-hydroxybufa-4,22-trienolide

46. 3.beta.-rhamnosido-14.beta.-hydroxy-.delta.(sup 4,22)-bufatrienolide

47. Wln: L E5 B666 Mutj A1 E1 Iq F- Et6ovj& O- Bt6otj Cq Dq Eq F1

48. Bufa-4,22-trienolide, 3-[(6-deoxy-.alpha.-l-mannopyranosyl)oxy]-14-hydroxy-, (3.beta.)-

49. Bufa-4,22-trienolide, 3.beta.-[(16-deoxy-.alpha.-l-mannosyl)oxy]-14-hydroxy-

50. Bufa-4,22-trienolide, 3.beta.-[(6-deoxy-.alpha.-l-mannopyranosyl)oxy]-14-hydroxy-

51. 5-[(3s,8r,9s,10r,13r,14s,17r)-14-hydroxy-10,13-dimethyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

2.3 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 530.6 g/mol
Molecular Formula C30H42O8
XLogP31.9
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count3
Exact Mass530.28796829 g/mol
Monoisotopic Mass530.28796829 g/mol
Topological Polar Surface Area126 Ų
Heavy Atom Count38
Formal Charge0
Complexity1070
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count5
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

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.)


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.)


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