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6-epicastanospermine

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Phytex Castanospermine

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Chemistry

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Also known as: 79831-76-8, Castinospermine, 6-epicastanospermine, 1,6,7,8-tetrahydroxyoctahydroindolizine, (1s,6s,7r,8r,8ar)-1,6,7,8-tetrahydroxyindolizidine, 6,7-diepicastanospermine

Molecular Formula

C₈H₁₅NO₄

Molecular Weight

189.21 g/mol

InChI Key

JDVVGAQPNNXQDW-TVNFTVLESA-N

FDA UNII

Q0I3184XM7

castanospermine is a natural product found in Alexa grandiflora, Alexa wachenheimii, and other organisms with data available.

1 2D Structure

Castanospermine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,6S,7R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol

2.1.2 InChI

InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1

2.1.3 InChI Key

JDVVGAQPNNXQDW-TVNFTVLESA-N

2.1.4 Canonical SMILES

C1CN2CC(C(C(C2C1O)O)O)O

2.1.5 Isomeric SMILES

C1CN2C[C@@H]([C@H]([C@@H]([C@H]2[C@H]1O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

Q0I3184XM7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1,6,7,8-tetrahydroxyoctahydroindolizine

2. 1-epicastanospermine

3. 6,7-diepicastanospermine

4. 6-epicastanospermine

5. Castinospermine

2.3.2 Depositor-Supplied Synonyms

1. 79831-76-8

2. Castinospermine

3. 6-epicastanospermine

4. 1,6,7,8-tetrahydroxyoctahydroindolizine

5. (1s,6s,7r,8r,8ar)-1,6,7,8-tetrahydroxyindolizidine

6. 6,7-diepicastanospermine

7. (1s,6s,7r,8r,8ar)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol

8. Chebi:27860

9. Q0i3184xm7

10. 79831-76-8 (free Base)

11. Nsc-625381

12. (1s,6s,7r,8r,8ar)-octahydroindolizine-1,6,7,8-tetrol

13. (1s,6s,7r,8r,8ar)-octahydroindolizine-1,6,7,8-tetraol

14. (1s-(1alpha,6beta,7alpha,8beta,8alphabeta))-octahydro-1,6,7,8-indolizinetetrol

15. Cts

16. Sr-01000597675

17. Mfcd00017555

18. Nsc 625381

19. Unii-q0i3184xm7

20. Indolizine Der.

21. Nsc625381

22. 2cbu

23. Octahydro-indolizine-1,6,7,8-tetraol

24. Cid54445

25. Cast

26. (1s,6s,7r,8r,8ar)-octahydro-1,6,7,8-indolizinetetrol

27. Molmap_000013

28. Upcmld-dp122

29. Castanospermine [mi]

30. Schembl61040

31. Bspbio_001552

32. Kbiogr_000272

33. Kbioss_000272

34. Mls000028641

35. Chembl311226

36. Upcmld-dp122:001

37. Upcmld-dp122:002

38. Upcmld-dp122:003

39. Bcbcmap01_000133

40. Bdbm36388

41. Kbio2_000272

42. Kbio2_002840

43. Kbio2_005408

44. Kbio3_000543

45. Kbio3_000544

46. Bio1_000396

47. Bio1_000885

48. Bio1_001374

49. Bio2_000272

50. Bio2_000752

51. Dtxsid601026043

52. Hms1361n14

53. Hms1791n14

54. Hms1989n14

55. Hms2232g11

56. Hms3266b08

57. Hms3402n14

58. Hms3414h05

59. Hms3678h05

60. Hy-n2022

61. Zinc3775177

62. Akos024458634

63. Ccg-208170

64. Cs-5633

65. Db01816

66. Idi1_034022

67. Smp1_000059

68. Ncgc00024773-02

69. Ncgc00024773-04

70. Smr000059227

71. B6439

72. Octahydro-indolizine-1,6,7,8-tetraol, 13

73. C02256

74. Q753104

75. Sr-01000597675-1

76. Sr-01000597675-4

77. W-203822

78. Castanospermine From Castanospermum Australe Seeds

79. 81041b9a-d148-44dc-a86d-c78d6abf9633

80. (1s,6s,7r,8r,8ar)-1,6,7,8-tetrahydroxyindolizidine, 98%

81. 1,6,7,8-indolizinetetrol, Octahydro-,?(1s,6s,7r,8r,8ar)-

82. [1s-(1?,6?,7?,8?,8a?)]-octahydro-1,6,7,8-indolizinetetrol

83. Castanospermine, >=94% (gc), Bioultra, From Castanospermum Australe Seeds

84. 1,6,7,8-indolizinetetrol, Octahydro-, (1s-(1alpha,6beta,7alpha,8beta,8abeta))-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₈H₁₅NO₄
Molecular Weight	189.21 g/mol
XLogP3	-2.2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	0
Exact Mass	189.10010796 g/mol
Monoisotopic Mass	189.10010796 g/mol
Topological Polar Surface Area	84.2 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	201
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
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

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Immunosuppressive Agents

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive 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.)

Glycoside Hydrolase Inhibitors

Compounds that inhibit or block the activity of GLYCOSIDE HYDROLASES such as ALPHA-AMYLASES and ALPHA-GLUCOSIDASES. (See all compounds classified as Glycoside Hydrolase Inhibitors.)

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