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Also known as: 1968-05-4, Diindolylmethane, Di(1h-indol-3-yl)methane, 3,3'-methylenebis-1h-indole, 3,3'-methylenediindole, Dim

Molecular Formula

C₁₇H₁₄N₂

Molecular Weight

246.31 g/mol

InChI Key

VFTRKSBEFQDZKX-UHFFFAOYSA-N

FDA UNII

SSZ9HQT61Z

Diindolylmethane is a phytonutrient and plant indole found in cruciferous vegetables including broccoli, Brussels sprouts, cabbage, cauliflower and kale, with potential anti-androgenic and antineoplastic activities. As a dimer of indole-3-carbinol, diindolylmethane (DIM) promotes beneficial estrogen metabolism in both sexes by reducing the levels of 16-hydroxy estrogen metabolites and increasing the formation of 2-hydroxy estrogen metabolites, resulting in increased antioxidant activity. Although this agent induces apoptosis in tumor cells in vitro, the exact mechanism by which DIM exhibits its antineoplastic activity in vivo is unknown.

1 2D Structure

Diindolylmethane

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(1H-indol-3-ylmethyl)-1H-indole

2.1.2 InChI

InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2

2.1.3 InChI Key

VFTRKSBEFQDZKX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C2C(=C1)C(=CN2)CC3=CNC4=CC=CC=C43

2.2 Other Identifiers

2.2.1 UNII

SSZ9HQT61Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2,2'-methylenebis(1h-indole)

2. Diindolylmethane

2.3.2 Depositor-Supplied Synonyms

1. 1968-05-4

2. Diindolylmethane

3. Di(1h-indol-3-yl)methane

4. 3,3'-methylenebis-1h-indole

5. 3,3'-methylenediindole

6. Dim

7. Arundine

8. 3-(1h-indol-3-ylmethyl)-1h-indole

9. 1h-indole, 3,3'-methylenebis-

10. Di(3-indolyl)methane

11. 3,3'-di-indolylmethane

12. Plant Indole

13. 3,3'-methylenebis(1h-indole)

14. 3,3,-diindolylmethane

15. Mfcd00195766

16. Ssz9hqt61z

17. Bis-1h-indol-3-ylmethane

18. Chebi:50182

19. 3,3'-methanediylbis(1h-indole)

20. Hb 236

21. 3,3 Inverted Exclamation Marka-diindolylmethane

22. 3-diindolyl Methane

23. 3,3'-diindolymethane

24. Diidolylmethane

25. Infemin

26. Ccris 5806

27. 33diindolylmethyle

28. Di-3-indolylmethane

29. Nsc708486

30. 3-3-diindolylmethane

31. 33'-diindolylmethane

32. Spectrum2_001711

33. Spectrum3_001989

34. Spectrum5_001955

35. Unii-ssz9hqt61z

36. Cbiol_001839

37. Oprea1_472633

38. Oprea1_740951

39. Bspbio_001290

40. Bspbio_003589

41. Cbdive_010856

42. Kbiogr_000010

43. Kbioss_000010

44. Mls006011847

45. Schembl325162

46. Spectrum1505331

47. Spbio_001722

48. 3,3'-di(indol-3-yl)methane

49. Bml3-f11

50. Chembl446452

51. 3,3'-diindolylmethane (dim)

52. Diindolylmethane [vandf]

53. Dtxsid8037047

54. Gtpl11208

55. Kbio2_000010

56. Kbio2_002578

57. Kbio2_005146

58. Kbio3_000019

59. Kbio3_000020

60. Kbio3_003002

61. Bio1_000125

62. Bio1_000614

63. Bio1_001103

64. Bio2_000010

65. Bio2_000490

66. Diindolylmethane, 3,3'-

67. Hms1361a12

68. Hms1791a12

69. Hms1989a12

70. Hms3402a12

71. Zinc187911

72. 3,3'-diindolylmethane, Aldrichcpr

73. Act06989

74. Albb-016048

75. Bcp00470

76. Ccg-39861

77. Gr-207

78. Hsci1_000069

79. S4728

80. Stk263696

81. Akos003627372

82. Am84671

83. Cs-1652

84. Db11875

85. Ks-5266

86. Nsc-708486

87. Sb16901

88. Idi1_033760

89. 3,3'-diindolylmethane [who-dd]

90. Ncgc00095348-01

91. Ncgc00095348-02

92. Ncgc00095348-03

93. Ncgc00095348-04

94. Ncgc00095348-05

95. Ncgc00095348-06

96. Ncgc00095348-07

97. Ac-11611

98. Hy-15758

99. Nci60_038418

100. Smr001828114

101. Sy038972

102. 3,3'-diindolylmethane, >=98% (hplc)

103. 3,3'-diindolylmethane, Analytical Standard

104. Db-011102

105. Ft-0614061

106. M1399

107. A16321

108. D-3720

109. 968d054

110. Q4634053

111. Brd-k37846922-001-05-2

112. Brd-k37846922-001-06-0

113. Brd-k37846922-001-09-4

114. C444299000

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₄N₂
Molecular Weight	246.31 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	0
Rotatable Bond Count	2
Exact Mass	246.115698455 g/mol
Monoisotopic Mass	246.115698455 g/mol
Topological Polar Surface Area	31.6 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	286
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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

Anticarcinogenic Agents

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)

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