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Oleoylethanolamide

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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

Oleoylethanolamide

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 Formula	C₂₀H₃₉NO₂
Molecular Weight	325.5 g/mol
XLogP3	6.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	17
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	49.3
Heavy Atom Count	23
Formal Charge	0
Complexity	277
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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