MolPort-001-742-490

Synopsis, Chemistry

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Also known as: 1180-71-8, Dictamnolactone, Obaculactone, Citrolimonin, Evodin, Limonine

Molecular Formula

C₂₆H₃₀O₈

Molecular Weight

470.5 g/mol

InChI Key

KBDSLGBFQAGHBE-MSGMIQHVSA-N

FDA UNII

L0F260866S

limonin is a natural product found in Flacourtia jangomas, Raulinoa echinata, and other organisms with data available.

1 2D Structure

MolPort-001-742-490

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione

2.1.2 InChI

InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1

2.1.3 InChI Key

KBDSLGBFQAGHBE-MSGMIQHVSA-N

2.1.4 Canonical SMILES

CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)C

2.1.5 Isomeric SMILES

C[C@@]12CC[C@H]3[C@]([C@@]14[C@H](O4)C(=O)O[C@H]2C5=COC=C5)(C(=O)C[C@@H]6[C@@]37COC(=O)C[C@@H]7OC6(C)C)C

2.2 Other Identifiers

2.2.1 UNII

L0F260866S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 7,16-dioxo-7,16-dideoxylimondiol

2. Obaculactone

2.3.2 Depositor-Supplied Synonyms

1. 1180-71-8

2. Dictamnolactone

3. Obaculactone

4. Citrolimonin

5. Evodin

6. Limonine

7. 7,16-dioxo-7,16-dideoxylimondiol

8. Limoni

9. Limonoic Acid, Di-delta-lactone

10. Evodia Fruit

11. Nsc 36508

12. Limonoic Acid 3,19:16,17-dilactone

13. Limonoate D-ring-lactone

14. (4as,6ar,8ar,8br,9as,12s,12as,14ar,14br)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1h,3h-oxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(6h,9ah)-trione

15. Chebi:16226

16. Limonoic Acid 3,19:16,17 Dilactone

17. L0f260866s

18. Dsstox_cid_25985

19. Dsstox_rid_81273

20. Dsstox_gsid_45985

21. (4as,6ar,8ar,8br,9as,12s,12as,14ar,14br)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1h,6h,8ah)-trione

22. 11h,13h-oxireno(d)pyrano(4',3':3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2h,5ah)-trione, 8-(3-furyl)decahydro-2,2,4a,8a-tetramethyl-

23. Limone

24. Mfcd00075922

25. (1r,2r,7s,10r,13r,14r,16s,19s,20s)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione

26. (4as,6ar,8ar,8br,9as,12r,12as,14ar,14br)-12-(3-furyl)-6,6,8a,12a-tetramethyldecahydro-3h-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6h,9ah)-trione

27. 11h,13h-oxireno(d)pyrano(4',3':3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2h,5ah)-trione, 8-(3-furanyl)decahydro-2,2,4a,8a-tetramethyl-, (2ar,4ar,4br,5as,8s,8as,10ar,10br,14as)-

28. 1809582-56-6

29. Rel-(4as,6ar,8ar,8br,9as,12s,12as,14ar,14br)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1h,6h,8ah)-trione

30. Cas-1180-71-8

31. Limonoic Acid Di-delta-lactone

32. 3-furyl(tetramethyl)[?]trione

33. Linonin

34. Nsc36508

35. Ccris 4047

36. Nsc-36508

37. Unii-l0f260866s

38. Ncgc00095714-01

39. Limonoic Acid, Di-.delta.-lactone

40. Ai3-37932

41. Limonin [mi]

42. Spectrum2_001728

43. Spectrum3_001012

44. Spectrum4_001140

45. Spectrum5_000935

46. Limonin, Analytical Standard

47. Bspbio_002763

48. Kbiogr_001659

49. Limonoic Acid Di-del.-lactone

50. Schembl320315

51. Spectrum1800018

52. Spbio_001776

53. Chembl517449

54. Dtxsid8045985

55. Acon1_001996

56. Kbio3_001983

57. Limonoic Acid Di-.delta.-lactone

58. Zinc4096134

59. Tox21_111513

60. Bdbm50418089

61. Ccg-38796

62. Akos015965307

63. Tox21_111513_1

64. Ac-8045

65. Cs-1237

66. Sdccgmls-0066837.p001

67. Ncgc00178483-01

68. Ncgc00178483-02

69. Ncgc00178483-04

70. Ncgc00178483-05

71. Ncgc00178483-14

72. Ncgc00263659-01

73. As-15249

74. Hy-17411

75. L0258

76. Limonin, From Citrus Seeds, >90% (hplc)

77. N1349

78. S2319

79. C03514

80. 180l718

81. A854522

82. Q-100083

83. Q2398745

84. Brd-k05906022-001-03-6

85. Brd-k05906022-001-05-1

86. Limone; Citrolimonin; Evodine; Dictamnolactone; Obaculactone

87. (4as,14br)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1h,3h-oxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(6h,9ah)-trione

88. (4as,6ar,8ar,8br,9as,12r,12as,14ar,14br)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-3h-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6h,9ah)-trione

89. 11h,13h-oxireno(d)pyrano(4',3':3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2h,5ah)-trione, 8-(3-furanyl)decahydro-2,2,4a,8a-tetramethyl-, (2ar-(2aalpha,4abeta,4br,5aalpha,8alpha,8aalpha,10aalpha,10br*,14aalpha))-

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₀O₈
Molecular Weight	470.5 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	1
Exact Mass	470.19406791 g/mol
Monoisotopic Mass	470.19406791 g/mol
Topological Polar Surface Area	105 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	1010
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1