Prestwick3_000436

Synopsis, Chemistry

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Also known as: 143-62-4, Cerberigenin, Echujetin, Thevetigenin, Evonogenin, Digitoxigenine

Molecular Formula

C₂₃H₃₄O₄

Molecular Weight

374.5 g/mol

InChI Key

XZTUSOXSLKTKJQ-CESUGQOBSA-N

FDA UNII

S63WOD4VOL

3 beta,14-Dihydroxy-5 beta-card-20(22)enolide. A cardenolide which is the aglycon of digitoxin. Synonyms: Cerberigenin; Echujetin; Evonogenin; Thevetigenin.

1 2D Structure

Prestwick3_000436

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[(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]-2H-furan-5-one

2.1.2 InChI

InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1

2.1.3 InChI Key

XZTUSOXSLKTKJQ-CESUGQOBSA-N

2.1.4 Canonical SMILES

CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)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=CC(=O)OC5)O)C)O

2.2 Other Identifiers

2.2.1 UNII

S63WOD4VOL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Uzarigenin

2.3.2 Depositor-Supplied Synonyms

1. 143-62-4

2. Cerberigenin

3. Echujetin

4. Thevetigenin

5. Evonogenin

6. Digitoxigenine

7. Uzarigenin

8. Mls002153810

9. 3-[(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]-2h-furan-5-one

10. S63wod4vol

11. Nsc 407806

12. Chebi:42219

13. 3beta,14-dihydroxy-5beta-card-20(22)-enolide

14. Nsc-407806

15. Smr001233182

16. 3-beta,14beta-dihydroxy-5-beta-card-20(22)-enolide

17. 3.beta.,14-dihydroxy-5.beta.-card-20(22)-enolide

18. .delta.20:22-3,14,21-trihydroxynorcholenic Acid Lactone

19. Card-20(22)-enolide, 3,14-dihydroxy-, (3.beta.,5.beta.)-

20. Dtx

21. Mls002701726

22. Unii-s63wod4vol

23. Nsc407806

24. 1lnm

25. 4-(3,14-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-5h-furan-2-one

26. Prestwick_169

27. Einecs 205-603-4

28. Mfcd00003687

29. Brn 0095448

30. 3-beta,14-dioxy-carden-(20:22)-olid

31. 3-beta,14-dioxy-digen-(20:22)-olid

32. Cardogenen-(20:22)-diol-(3-beta,14)

33. Prestwick0_000436

34. Prestwick1_000436

35. Prestwick2_000436

36. Prestwick3_000436

37. Digitoxigenin [mi]

38. (+)-digitoxigenin

39. Chembl1453

40. 3-beta,14-dioxy-digen-(20:22)-olid [german]

41. Schembl61224

42. Bspbio_000452

43. 3-beta,14-dihydroxy-5-beta-card-20(22)-enolide

44. 3-beta,14-dioxy-carden-(20:22)-olid [german]

45. 5-18-03-00348 (beilstein Handbook Reference)

46. Cardogenen-(20:22)-diol-(3-beta,14) [german]

47. Spbio_002391

48. Bpbio1_000498

49. Delta20:22-3,14,21-trihydroxynorcholenic Acid Lactone

50. Bdbm66977

51. Cid_4369270

52. Card-20(22)-enolide, 3,14-dihydroxy-, (3beta,5beta)-

53. Dtxsid80162276

54. 3-beta,14-dihydroxy-5-beta,14-beta-card-20(22)-enolide

55. Card-20(22)-enolide, 3,14-dihydroxy-, (3-beta,5-beta)-

56. Delta-sup(20:22)-3,14,21-trihydroxynorcholenic Acid Lactone

57. Delta-sup(20:22)-3,14,21-trihydroxynorcholenicacid Lactone

58. Hms1569g14

59. Hms2096g14

60. Hms2231j22

61. Hms3713g14

62. Zinc3875959

63. Lmst01120001

64. Akos015915862

65. Ccg-220436

66. Db04177

67. Ncgc00179555-01

68. 3-.beta.,14-dioxy-digen-(20:22)-olid

69. D0541

70. Cardogenen-(20:22)-diol-(3-.beta.,14)

71. 5.beta.-card-20(22)-enolide,14-dihydroxy-

72. 3-beta, 14-beta-card-20(22)-enolide

73. Q411469

74. Sr-01000841188

75. 5beta-card-20(22)-enolide, 3beta,14-dihydroxy-

76. Sr-01000841188-2

77. Brd-k18518344-001-03-5

78. .delta.20:22-3,21-trihydroxynorcholenic Acid Lactone

79. 5.beta.-card-20(22)-enolide, 3.beta.,14-dihydroxy

80. 5.beta.-card-20(22)-enolide, 3.beta.,14-dihydroxy-

81. Wln: L E5 B666tj A1 E1 F- Dt5ov Cutj Iq Oq

82. (3alpha,5beta,8alpha)-3,14-dihydroxycard-20(22)-enolide

83. 5-beta-card-20(22)-enolide, 3-beta,14-dihydroxy-

84. .delta.-sup(20:22)-3,21-trihydroxynorcholenic Acid Lactone

85. 3,14-dihydroxycard-20(22)-enolide, (3.beta.,5.beta.)- #

86. Card-20(22)-enolide,14-dihydroxy-, (3.beta.,5.beta.)-

87. .delta.-sup(20:22)-3,14,21-trihydroxynorcholenicacid Lactone

88. 3-[(3s,5r,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,14-bis(oxidanyl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2h-furan-5-one

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₃₄O₄
Molecular Weight	374.5 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Exact Mass	374.24570956 g/mol
Monoisotopic Mass	374.24570956 g/mol
Topological Polar Surface Area	66.8 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	686
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