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2D Structure
Also known as: 111-58-0, N-(2-hydroxyethyl)oleamide, Oleoyl ethanolamide, (z)-n-(2-hydroxyethyl)octadec-9-enamide, Oleoyl monoethanolamide, Oleic monoethanolamide
Molecular Formula
C20H39NO2
Molecular Weight
325.5  g/mol
InChI Key
BOWVQLFMWHZBEF-KTKRTIGZSA-N
FDA UNII
1HI5J9N8E6

activates nuclear receptor peroxisome proliferator-activated receptor alpha (PPAR-alpha) with the effect of stimulating lipolysis
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(Z)-N-(2-hydroxyethyl)octadec-9-enamide
2.1.2 InChI
InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
2.1.3 InChI Key
BOWVQLFMWHZBEF-KTKRTIGZSA-N
2.2 Other Identifiers
2.2.1 UNII
1HI5J9N8E6
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 111-58-0

2. N-(2-hydroxyethyl)oleamide

3. Oleoyl Ethanolamide

4. (z)-n-(2-hydroxyethyl)octadec-9-enamide

5. Oleoyl Monoethanolamide

6. Oleic Monoethanolamide

7. N-(9z-octadecenoyl)-ethanolamine

8. N-(cis-9-octadecenoyl) Ethanolamine

9. 1hi5j9n8e6

10. 9-octadecenamide, N-(2-hydroxyethyl)-

11. Dtxsid1044516

12. 9-octadecenamide, N-(2-hydroxyethyl)-, (9z)-

13. Chebi:71466

14. Refchem:856533

15. Dtxcid9024516

16. 203-884-8

17. Oleoylethanolamine

18. N-oleoylethanolamine

19. Oleylethanolamide

20. Oleamide Mea

21. N-oleoyl Ethanolamine

22. N-oleoylethanolamide

23. N-oleoyl Ethanolamide

24. Mfcd00045972

25. N-(2-hydroxyethyl)-9-octadecenamide

26. (9z)-n-(2-hydroxyethyl)octadec-9-enamide

27. Oleic Acid Ethanolamide

28. N-(hydroxyethyl)oleamide

29. N-(hydroxyethyl) Oleamide

30. Oea

31. Chembl280065

32. N-?oleoylethanolamide

33. Sr-01000076041

34. Einecs 203-884-8

35. Unii-1hi5j9n8e6

36. Monoethanolamine Oleic Acid Amide

37. 9-octadecenamide, N-(2-hydroxyethyl)-, (z)-

38. 5ym

39. Olemsartan Medoximil

40. C18:1 Anandamide

41. Oleoyl 1-ethanolamide

42. Tocris-1484

43. N-oleoyl-2-aminoethanol

44. Oleoylethanolamide (oea)

45. Spectrum5_002037

46. Lopac-o-0383

47. Oleic Acid Monoethanolamide

48. Lopac0_000942

49. Mls002153155

50. Schembl177713

51. Gtpl2661

52. Orb1309303

53. Bdbm29080

54. N-(9z-octadecenoyl) Ethanolamine

55. Glxc-22224

56. Hms2233e21

57. Hms3262n06

58. Hms3412d21

59. Hms3649j05

60. Hms3676d21

61. Oleylethanolamide [who-dd]

62. Nae 18:1

63. Tox21_500942

64. Lmfa08040015

65. Msk159624

66. N-oleoylethanolamine, ~98% (tlc)

67. Nae(18:1)

68. Akos015839895

69. N-(2-hydroxyethyl)-9z-octadecenamide

70. Ccg-205023

71. Lp00942

72. Msk159624-100m

73. Sdccgsbi-0050916.p002

74. Msk159624-1000m

75. Ncgc00015761-01

76. Ncgc00015761-02

77. Ncgc00015761-03

78. Ncgc00015761-04

79. Ncgc00015761-05

80. Ncgc00015761-06

81. Ncgc00015761-07

82. Ncgc00015761-12

83. Ncgc00025182-01

84. Ncgc00025182-02

85. Ncgc00025182-04

86. Ncgc00025182-05

87. Ncgc00025182-06

88. Ncgc00261627-01

89. As-15152

90. Bp-43134

91. Fo180525

92. Smr001230650

93. Sy102076

94. Hy-107542

95. Cs-0028847

96. Eu-0100942

97. Ns00013916

98. O0345

99. C20792

100. D82195

101. O 0383

102. 111o580

103. 9-octadecenamide, N-(2-hydroxyethyl)-, Z

104. A802386

105. Q7086404

106. Sr-01000076041-1

107. Sr-01000076041-3

108. Sr-01000076041-8

109. Brd-k66956375-001-11-3

110. C18:1 Anandamide, 9z-octadecenoylethanolamide, Powder

111. N-oleoylethanolamine Solution In Methanol, 1000ug/ml

112. N-oleoylethanolamine Solution In Methanol, 100ug/ml

113. (z)-n-(2-hydroxyethyl)octadec-9-enamide;oleoylethanolamide

114. N-oleoylethanolamide; Oleamide Mea; Oleic Acid Monoethanolamide

115. N-oleoyl Ethanolamine, Oleoyl Monoethanolamide, Oleoylethanolamide

116. N-oleoylethanolamine; (9z)-n-(2-hydroxyethyl)-9-octadecenamide; Oleic Acid Ethanolamide

2.4 Create Date
2006-01-13
3 Chemical and Physical Properties
Molecular Weight 325.5 g/mol
Molecular Formula C20H39NO2
XLogP36.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count17
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area49.3
Heavy Atom Count23
Formal Charge0
Complexity277
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Mechanism of Action

Oleoylethanolamide (OEA) is a major N-acylethanolamine and an endogenous ethanolamide fatty acid. Although it is an endocannabinoids-like compound, it does not bind to cannabinoid receptors. Instead, this lipid sensor is an agonist at peroxisome proliferator-activated receptor- (PPAR-) agonist while also being an inhibitor of ceramidase and thereby the sphingolipid signaling pathway.