Anandamide

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Also known as: Arachidonylethanolamide, 94421-68-8, Arachidonoyl ethanolamide, N-arachidonoylethanolamine, N-arachidonoyl ethanolamine, Arachidonoylethanolamide

Molecular Formula

C₂₂H₃₇NO₂

Molecular Weight

347.5 g/mol

InChI Key

LGEQQWMQCRIYKG-DOFZRALJSA-N

FDA UNII

UR5G69TJKH

anandamide is a natural product found in Homo sapiens with data available.

1 2D Structure

Anandamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide

2.1.2 InChI

InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-

2.1.3 InChI Key

LGEQQWMQCRIYKG-DOFZRALJSA-N

2.1.4 Canonical SMILES

CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO

2.1.5 Isomeric SMILES

CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO

2.2 Other Identifiers

2.2.1 UNII

UR5G69TJKH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5,8,11,14-eicosatetraenamide, N-(2-hydroxyethyl)-

2. 5,8,11,14-eicosatetraenoylethanolamide

3. Anandamide (20.4,n-6)

4. Arachidonoyl Ethanolamide

5. Arachidonoylethanolamide

6. Arachidonylethanolamide

7. N-(2-hydroxyethyl)arachidonamide

8. N-arachidonoyl-2-hydroxyethylamide

9. N-arachidonoylethanolamide

10. N-arachidonoylethanolamine

2.3.2 Depositor-Supplied Synonyms

1. Arachidonylethanolamide

2. 94421-68-8

3. Arachidonoyl Ethanolamide

4. N-arachidonoylethanolamine

5. N-arachidonoyl Ethanolamine

6. Arachidonoylethanolamide

7. (5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide

8. Aea

9. Anandamide (20.4, N-6)

10. N-arachidonoyl-2-hydroxyethylamide

11. Arachidonoyl-ea

12. N-(2-hydroxyethyl)anachidonamide

13. 5,8,11,14-eicosatetraenoylethanolamide

14. Anandamide(20:4, N-6)

15. Anandamide (20:4, N-6)

16. Arachidonic Acid N-(hydroxyethyl)amide

17. N-(5z,8z,11z,14z-eicosatetraenoyl)-ethanolamine

18. Ur5g69tjkh

19. Aea-d8

20. 5,8,11,14-eicosatetraenamide, N-(2-hydroxyethyl)-, (5z,8z,11z,14z)-

21. Chembl15848

22. Chebi:2700

23. 5,8,11,14-eicosatetraenamide, N-(2-hydroxyethyl)-, (all-z)-

24. [3h]anandamide

25. 924894-98-4

26. N-(5z,8z,11z,14z-icosatetraenoyl)-ethanolamide

27. Arachidonoylethanolamide (aea)

28. Unii-ur5g69tjkh

29. N-(2-hydroxyethyl)-5z,8z,11z,14z-eicosatetraenamide

30. Annh

31. [14c]anandamide

32. Arachidonyl Ethanolamide

33. N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide (all-z)-

34. Anandamide [mi]

35. Schembl43143

36. Bspbio_001533

37. N-arachidonoylaminoethan-2-ol

38. Bml2-b09

39. Gtpl2364

40. Bdbm22988

41. Dtxsid301017453

42. Hms1361m15

43. Hms1791m15

44. Hms1989m15

45. Hms3402m15

46. Hms3649b09

47. Zinc3809850

48. (5z,8z,11z,14z)-n-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide

49. Lmfa08040001

50. Nae(20:4)

51. Akos015951333

52. Ccg-208077

53. Idi1_034003

54. Smp2_000328

55. Ncgc00161195-03

56. Ncgc00161195-04

57. Ncgc00161195-05

58. Ncgc00161195-06

59. Ncgc00161195-07

60. Ba166586

61. Anandamide (in Tocrisolvetrade Mark 100)

62. Arachidonylethanolamide, >=97.0% (tlc), Oil

63. L000111

64. Q410228

65. Sr-01000946635

66. Sr-01000946635-1

67. Brd-k42352790-001-03-8

68. (all-z)-n-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide

69. N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide (all-z)

70. (5z,8z,11z,14z)- N-(2-hydroxyethyl)- 5,8,11,14-eicosatetraenamide

71. C20:4 Anandamide (aea), 5z,8z,11z,14z-eicosatetraenoylethanolamide, Neat Oil

72. E7y

2.4 Create Date

2005-06-01

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₃₇NO₂
Molecular Weight	347.5 g/mol
XLogP3	5.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	16
Exact Mass	347.282429423 g/mol
Monoisotopic Mass	347.282429423 g/mol
Topological Polar Surface Area	49.3 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	408
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

Cannabinoid Receptor Agonists

Compounds that interact with and stimulate the activity of CANNABINOID RECEPTORS. (See all compounds classified as Cannabinoid Receptor Agonists.)