Fumagillin

Synopsis, Chemistry

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Also known as: 23110-15-8, Fugillin, Fumidil, Amebacilin, Fumagilline, Fumagillinum

Molecular Formula

C₂₆H₃₄O₇

Molecular Weight

458.5 g/mol

InChI Key

NGGMYCMLYOUNGM-CSDLUJIJSA-N

FDA UNII

7OW73204U1

fumagillin is a natural product found in Aspergillus fumigatus with data available.

1 2D Structure

Fumagillin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2E,4E,6E,8E)-10-[[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy]-10-oxodeca-2,4,6,8-tetraenoic acid

2.1.2 InChI

InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+/t19-,20-,23-,24-,25+,26+/m1/s1

2.1.3 InChI Key

NGGMYCMLYOUNGM-CSDLUJIJSA-N

2.1.4 Canonical SMILES

CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)OC(=O)C=CC=CC=CC=CC(=O)O)OC)C

2.1.5 Isomeric SMILES

CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@]23CO3)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O)OC)C

2.2 Other Identifiers

2.2.1 UNII

7OW73204U1

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fumidil B

2.3.2 Depositor-Supplied Synonyms

1. 23110-15-8

2. Fugillin

3. Fumidil

4. Amebacilin

5. Fumagilline

6. Fumagillinum

7. Fumagilina

8. (-)-fumagillin

9. Zgn-201

10. Amebacillin

11. Fugilin

12. Chembl32838

13. 2,4,6,8-decatetraenedioic Acid, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro(2,5)oct-6-yl Ester

14. Fumagillin Dch

15. Chebi:48635

16. Nsc-9168

17. 7ow73204u1

18. Dsstox_cid_20736

19. Dsstox_rid_79580

20. Dsstox_gsid_40736

21. (2e,4e,6e,8e)-10-({(3r,4s,5s,6r)-5-methoxy-4-[(2r,3r)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic Acid

22. Fumagillina

23. Flisint

24. (2e,4e,6e,8e)-10-(((3r,4s,5s,6r)-5-methoxy-4-((2r,3r)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-yl)oxy)-10-oxodeca-2,4,6,8-tetraeno

25. Cas-23110-15-8

26. Fumagillina [dcit]

27. U 5762

28. Fumagilina [inn-spanish]

29. Fumagilline [inn-french]

30. Fumagillinum [inn-latin]

31. Nsc9168

32. Fumagillin [inn:ban:dcf]

33. Ccris 9025

34. Unii-7ow73204u1

35. Ncgc00163699-01

36. H-3

37. Nsc 9168

38. Einecs 245-433-8

39. Fumagillin [mi]

40. Fumagillin [inn]

41. Fumagillin [mart.]

42. Schembl8130

43. Fumagillin [who-dd]

44. Dtxsid7040736

45. Schembl15263952

46. (2e,4e,6e,8e)-mono[(3r,4s,5s,6r)-5-methoxy-4-[(2r,3r)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] 2,4,6,8-decatetraenedioic Acid Ester

47. Ex-a2890

48. Hy-b0751

49. Zinc4098264

50. Tox21_112066

51. Tox21_302410

52. Bdbm50113436

53. S7784

54. Akos024456768

55. Db02640

56. Lmpr0103060003

57. Ncgc00163699-02

58. Ncgc00163699-07

59. Ncgc00255568-01

60. Ac-35866

61. Bs-16576

62. Sr-90144

63. D81922

64. Q120199

65. (2e,4e,6e,8e)-10-(((3r,4s,5s,6r)-5-methoxy-4-((2r,3r)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-yl)oxy)-10-oxodeca-2,4,6,8-tetraenoic Acid

66. 127913-45-5

67. 2,4,6,8-decatetraenedioic Acid, 1-((3r,4s,5s,6r)-5-methoxy-4-((2r,3r)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl)-1-oxaspiro(2.5)oct-6-yl) Ester, (2e,4e,6e,8e)-

68. 2,4,6,8-decatetraenedioic Acid, Mono((3r,4s,5s,6r)-5-methoxy-4-((2r,3r)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl)-1-oxaspiro(2.5)oct-6-yl) Ester, (2e,4e,6e,8e)-

69. 2,4,6,8-decatetraenedioic Acid, Mono(4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro(2.5)oct-6-yl) Ester

70. 2,4,6,8-decatetraenedioic Acid, Mono(4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro(2.5)oct-6-yl) Ester (van)

71. 2,4,6,8-decatetraenedioic Acid, Mono(5-methoxy-4-(2-methyl-3-(3-methyl-2-butenyl)oxiranyl)-1-oxaspiro(2.5)oct-6-yl) Ester, (3r- (3.alpha.,4.alpha.(2r*,3r*),5.beta.,6.beta.(2e,4e,6e,8e)))-

72. 2,4,6,8-decatetraenedioic Acid, Mono(5-methoxy-4-(2-methyl-3-(3-methyl-2-butenyl)oxiranyl)-1-oxaspiro(2.5)oct-6-yl) Ester, (3r-(3alp

73. 2,4,6,8-decatetraenedioic Acid, Mono[(3r,4s,5s,6r)-5-methoxy-4-[(2r,3r)-2-methyl-3-(3-methyl-2-buten-1-yl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] Ester, (2e,4e,6e,8e)-

74. Antibiotic Obtained From Cultures Of Aspergillus Fumigatus, Or The Same Substance Produced By Any Other Means

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₄O₇
Molecular Weight	458.5 g/mol
XLogP3	4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	11
Exact Mass	458.23045342 g/mol
Monoisotopic Mass	458.23045342 g/mol
Topological Polar Surface Area	97.9 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	879
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	4
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Angiogenesis Inhibitors

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)

Anti-Bacterial Agents

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

Antiprotozoal Agents

Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

4.2 ATC Code

P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01A - Agents against amoebiasis and other protozoal diseases

P01AX - Other agents against amoebiasis and other protozoal diseases

P01AX10 - Fumagillin