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Chemistry

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Also known as: 476-32-4, Stylophorin, Chelidonin, (+)-chelidonine, Khelidonin, Helidonine

Molecular Formula

C₂₀H₁₉NO₅

Molecular Weight

353.4 g/mol

InChI Key

GHKISGDRQRSCII-ZOCIIQOWSA-N

FDA UNII

4UDG3LY0GT

chelidonine is a natural product found in Sarcocapnos baetica, Sarcocapnos saetabensis, and other organisms with data available.

1 2D Structure

Chelidonine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol

2.1.2 InChI

InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1

2.1.3 InChI Key

GHKISGDRQRSCII-ZOCIIQOWSA-N

2.1.4 Canonical SMILES

CN1CC2=C(C=CC3=C2OCO3)C4C1C5=CC6=C(C=C5CC4O)OCO6

2.1.5 Isomeric SMILES

CN1CC2=C(C=CC3=C2OCO3)[C@@H]4[C@H]1C5=CC6=C(C=C5C[C@@H]4O)OCO6

2.2 Other Identifiers

2.2.1 UNII

4UDG3LY0GT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Chelidonine Bisulfate

2. Chelidonine Hydrochloride

3. Chelidonine Sulfate

4. Chelidonine Tartrate

2.3.2 Depositor-Supplied Synonyms

1. 476-32-4

2. Stylophorin

3. Chelidonin

4. (+)-chelidonine

5. Khelidonin

6. Helidonine

7. Stylophorine

8. Chebi:31389

9. 4udg3ly0gt

10. 8k7ek8446j

11. Chelidoniny

12. (5br,6s,12bs)-13-methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol

13. Chelidonin [german]

14. Chelidoniny [polish]

15. Unii-8k7ek8446j

16. Nsc646661

17. (1)-chelidonine

18. (1,3)benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5br,6s,12bs)-

19. [1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5br,6s,12bs)-

20. Einecs 207-504-1

21. Chelidonine (+-)-

22. Prestwick0_000587

23. Prestwick1_000587

24. Prestwick2_000587

25. Prestwick3_000587

26. Unii-4udg3ly0gt

27. Chelidonine [inci]

28. Bspbio_000434

29. Chelidonine [who-dd]

30. Diphylline (alkaloid)

31. Chelidonine (+)-form

32. Schembl563820

33. Spbio_002653

34. Bpbio1_000478

35. Chembl496867

36. Megxp0_001421

37. Acon1_000007

38. Chelidonine, (+/-)-

39. Dtxsid10878474

40. Hms3886n18

41. Hy-n2369

42. Chelidonine (+)-form [mi]

43. Chelidonine, >=97.0% (hplc)

44. Einecs 243-662-8

45. Bdbm50480259

46. Mfcd00069660

47. S9154

48. Zinc30727894

49. Akos016010202

50. Ccg-208430

51. Chelidonine (+/-)-form [mi]

52. Ncgc00167959-01

53. Ncgc00167959-02

54. Ncgc00167959-03

55. Ncgc00167959-05

56. Ncgc00167959-12

57. Ac-34033

58. Cs-0022550

59. 476c324

60. Sr-05000002251

61. Q-100506

62. Q1069066

63. Sr-05000002251-2

64. Brd-k32828673-001-01-5

65. Brd-k32828673-002-03-9

66. (1,3)benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5br,6s,12bs)-rel-

67. (1s,12s,13r)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol

68. (5br-(5b.alpha.,6.beta.,12b.alpha.))-5b,6,7,12b,13,14-hexahydro-13-methyl(1,3)benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridin-6-ol

69. 5b,6,7,12b,13,14-hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenan-thridin-6-ol

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₉NO₅
Molecular Weight	353.4 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	0
Exact Mass	353.12632271 g/mol
Monoisotopic Mass	353.12632271 g/mol
Topological Polar Surface Area	60.4 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	560
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1