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Immunomycin

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Chemistry

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Also known as: Immunomycin, 104987-12-4, Fk520, Fr 900520, Fk 520, L-683590

Molecular Formula

C₄₃H₆₉NO₁₂

Molecular Weight

792.0 g/mol

InChI Key

ZDQSOHOQTUFQEM-NURRSENYSA-N

FDA UNII

AUF4U5NSJK

immunomycin is a natural product found in Streptomyces hygroscopicus and Streptomyces ascomycinicus with data available.

1 2D Structure

Immunomycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone

2.1.2 InChI

InChI=1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29-,30+,31-,32+,33-,35+,36-,37-,38+,39+,43+/m0/s1

2.1.3 InChI Key

ZDQSOHOQTUFQEM-NURRSENYSA-N

2.1.4 Canonical SMILES

CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC)C)C

2.1.5 Isomeric SMILES

CC[C@@H]1/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]4CC[C@H]([C@@H](C4)OC)O)/C)O)C)OC)OC)C)\C

2.2 Other Identifiers

2.2.1 UNII

AUF4U5NSJK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Changchuanmycin

2. Fk 520

3. Fk-520

4. Fr 900520

5. Fr-900520

6. Immunomycin

7. Tacrolimus Related Compound A

2.3.2 Depositor-Supplied Synonyms

1. Immunomycin

2. 104987-12-4

3. Fk520

4. Fr 900520

5. Fk 520

6. L-683590

7. Auf4u5nsjk

8. Fk-520

9. L 683590

10. Chembl8597

11. Chebi:29582

12. Fr-900520

13. 11011-38-4

14. Ascomycin From Streptomyces Hygroscopicus Var. Ascomyceticus

15. Changchuanmycin

16. Ascomycin(fk 520)

17. (3s,4r,5s,8r,9e,12s,14s,15r,16s,18r,19r,22r,26as)-8-ethyl-5,19-dihydroxy-3-{(1e)-1-[(1r,3r,4r)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3h-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4h,23h)-tetrone

18. C43h69no12

19. Unii-auf4u5nsjk

20. Tacrolimus Related Compound A

21. Ascomycin Solution

22. Fr 520

23. Mfcd06198665

24. Nsc 106410

25. Nsc-106410

26. Ascomycin (fk520)

27. Schembl25512

28. Bspbio_001318

29. L 683,590

30. L-683,590

31. Chebi:94818

32. Dtxsid80894126

33. Hms1361b20

34. Hms1791b20

35. Hms1989b20

36. Hms3402b20

37. Ex-a1796

38. Bdbm50068939

39. Fr-520

40. S7411

41. Akos015916691

42. Zinc169289416

43. Ccg-270483

44. Cs-1516

45. Idi1_033788

46. Ncgc00163418-01

47. Ncgc00163418-02

48. 15,19-epoxy-3h-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4h,23h)-tetrone, 8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetram

49. Hy-13557

50. Ascomycin (fk 520, Fr 900520, Imm

51. Tacrolimus Related Compound A [usp-rs]

52. 011a384

53. Q4803998

54. Tacrolimus Related Compound A [usp Impurity]

55. Brd-k88998544-001-02-4

56. Brd-k99369265-001-01-4

57. Tacrolimus Impurity, Ascomycin- [usp Impurity]

58. Tacrolimus Monohydrate Impurity A [ep Impurity]

59. (1r,9s,12s,13r,14s,17r,18e,21s,23s,24r,25s,27r)-17-ethyl-1,14-dihydroxy-12-[(1e)-1-[(1r,3r,4r)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0?,?]octacos-18-ene-2,3,10,16-tetrone

60. (1r,9s,12s,13r,14s,17r,18e,21s,23s,24r,25s,27r)-17-ethyl-1,14-dihydroxy-12-[(e)-1-[(1r,3r,4r)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone

61. (3s,4r,5s,8r,9e,12s,14s,15r,16s,18r ,19r,26as)-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,1 9,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1e )-2-[(1r,3r,4r)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetrameth Yl-15,19-epoxy-3h-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4h,23h)tetrone

62. (3s,4r,5s,8r,9e,12s,14s,15r,16s,18r,19r,26as)-8-ethyl-5,19-dihydroxy-3-{(1e)-1-[(1r,3r,4r)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3h-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4h,23h)-tetrone

63. (3s,4r,5s,8r,9e,12s,14s,15r,16s,18r,19r,26as)-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1e)-2-[(1r,3r,4r)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3h-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4h,23h)tetrone

64. (ascomycin)17-ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone

65. (e)-(9s,12s,13r,14s,17r,21s,23s,24r,25s,27s)-17-ethyl-1,14-dihydroxy-12-[(e)-2-((1r,3r,4r)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone

66. (e)-(s)-17-ethyl-1,14-dihydroxy-12-[(e)-2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]oct Acos-18-ene-2,3,10,16-tetraone

67. (e)-17-ethyl-1,14-dihydroxy-12-[(e)-2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone

68. 135635-46-0

69. 15,19-epoxy-3h-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4h,23h)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-8-ethyl-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3s-(3r*(e(1s*,3s*,4s*)),4s*,19s*,26ar*))-

70. 17-ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₄₃H₆₉NO₁₂
Molecular Weight	792.0 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	6
Exact Mass	791.48197664 g/mol
Monoisotopic Mass	791.48197664 g/mol
Topological Polar Surface Area	178 Å²
Heavy Atom Count	56
Formal Charge	0
Complexity	1430
Isotope Atom Count	0
Defined Atom Stereocenter Count	14
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

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.)

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