4-Demethyl-Epipodophyllotoxin

Synopsis, Chemistry

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Also known as: 6559-91-7, 4'-dmep, 4-demethylepipodophyllotoxin, (-)-4'-demethylepipodophyllotoxin, 4'-o-demethylepipodophyllotoxin, Dmep

Molecular Formula

C₂₁H₂₀O₈

Molecular Weight

400.4 g/mol

InChI Key

YVCVYCSAAZQOJI-JHQYFNNDSA-N

FDA UNII

X0S6I23X6L

1 2D Structure

4-Demethyl-Epipodophyllotoxin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

2.1.2 InChI

InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1

2.1.3 InChI Key

YVCVYCSAAZQOJI-JHQYFNNDSA-N

2.1.4 Canonical SMILES

COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O

2.1.5 Isomeric SMILES

COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O

2.2 Other Identifiers

2.2.1 UNII

X0S6I23X6L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4'-demethyl Epipodophyllotoxin

2.3.2 Depositor-Supplied Synonyms

1. 6559-91-7

2. 4'-dmep

3. 4-demethylepipodophyllotoxin

4. (-)-4'-demethylepipodophyllotoxin

5. 4'-o-demethylepipodophyllotoxin

6. Dmep

7. X0s6i23x6l

8. Chebi:74422

9. (10r,11r,15r,16s)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

10. (5r,5ar,8ar,9s)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5ah)-one

11. (5s,5ar,8ar,9r)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

12. (5r-(5alpha,5abeta,8aalpha,9beta))-5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one

13. (5s,5ar,8ar,9r)-9-(3,5-dimethoxy-4-oxidanyl-phenyl)-5-oxidanyl-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one

14. Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5r,5ar,8ar,9s)-

15. Teniposide Related Compound A

16. Brn 1358259

17. Unii-x0s6i23x6l

18. 4'-demethyl-epipodophyllotoxin

19. Etoposide Aglycone

20. Ncgc00161927-01

21. Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5r,5ar,8ar,9s)-

22. Dsstox_cid_28668

23. Dsstox_rid_82938

24. Dsstox_gsid_48742

25. Demethylpodophyllotoxin, 4'-

26. Chembl31929

27. Epi-4'-demethylpodophyllotoxin

28. Schembl9885196

29. Dtxsid7048742

30. 4'-demethyl-9-epipodophyllotoxin

31. Epipodophyllotoxin, 4'-demethyl-

32. 4'-o-demethyl-4-epipodophyllotoxin

33. Ex-a1205

34. Zinc5670074

35. (-)-4'-demethyl-epipodophyllotoxin

36. Tox21_113196

37. Mfcd00189421

38. S2254

39. Akos015896348

40. Ac-7468

41. Ccg-208563

42. Cs-1426

43. 4'-demethyl Epi-podophyllotoxin (dmep)

44. As-18736

45. Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5r-(5-alpha,5a-beta,8a-alpha,9-beta))-

46. Hy-17435

47. Cas-6559-91-7

48. D5653

49. C21185

50. Teniposide Related Compound A [usp-rs]

51. A935071

52. Sr-05000002194

53. Q-100747

54. Sr-05000002194-2

55. Teniposide Related Compound A [usp Impurity]

56. Q27144659

57. (10r,11r,15r,16s)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one

58. (5r,5ar,8ar,9s)-5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one

59. (5r,5ar,8ar,9s)-5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one

60. (5r,5ar,8ar,9s)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5ah)-on

61. (5s,5ar,8ar,9r)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5h-isobenzofuro[6,5-f][1,3]benzodioxol-8-one

62. 89o

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₀O₈
Molecular Weight	400.4 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	3
Exact Mass	400.11581759 g/mol
Monoisotopic Mass	400.11581759 g/mol
Topological Polar Surface Area	104 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	614
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1