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Arachidonic Acid

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Also known as: 506-32-1, Arachidonate, (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoic acid, Immunocytophyte, (all-z)-5,8,11,14-eicosatetraenoic acid, Cis-5,8,11,14-eicosatetraenoic acid

Molecular Formula

C₂₀H₃₂O₂

Molecular Weight

304.5 g/mol

InChI Key

YZXBAPSDXZZRGB-DOFZRALJSA-N

FDA UNII

27YG812J1I

An unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.

1 2D Structure

Arachidonic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid

2.1.2 InChI

InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

2.1.3 InChI Key

YZXBAPSDXZZRGB-DOFZRALJSA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

27YG812J1I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (all-z)-5,8,11,14-eicosatetraenoic Acid

2. Arachidonate, Sodium

3. Arachidonic Acid, (all-z)-isomer, 1-(14)c-labeled

4. Arachidonic Acid, (all-z)-isomer, 3h-labeled

5. Arachidonic Acid, Ammonium Salt, (all-z)-isomer

6. Arachidonic Acid, Cerium Salt, (all-z)-isomer

7. Arachidonic Acid, Cesium Salt, (all-z)-isomer

8. Arachidonic Acid, Lithium Salt, (all-z)-isomer

9. Arachidonic Acid, Potassium Salt, (all-z)-isomer

10. Arachidonic Acid, Sodium Salt

11. Arachidonic Acid, Sodium Salt, (all-z)-isomer

12. Arachidonic Acid, Zinc Salt, (all-z)-isomer

13. Sodium Arachidonate

14. Vitamin F

2.3.2 Depositor-Supplied Synonyms

1. 506-32-1

2. Arachidonate

3. (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoic Acid

4. Immunocytophyte

5. (all-z)-5,8,11,14-eicosatetraenoic Acid

6. Cis-5,8,11,14-eicosatetraenoic Acid

7. 5,8,11,14-eicosatetraenoic Acid, (all-z)-

8. 5z,8z,11z,14z-eicosatetraenoic Acid

9. All-cis-5,8,11,14-eicosatetraenoic Acid

10. Icosa-5,8,11,14-tetraenoic Acid

11. (5z,8z,11z,14z)-5,8,11,14-eicosatetraenoic Acid

12. Chembl15594

13. Chebi:15843

14. 27yg812j1i

15. 5z,8z,11z,14z-icosatetraenoic Acid

16. Fa 20:4

17. Arachidonic Acid (20:4, N-6)

18. 5,8,11,14-eicosatetraenoic Acid

19. C20:4

20. [1-14c]arachidonic Acid

21. (14c)arachidonic Acid

22. Arachidonic Acid, 99%

23. Arachidonicacid

24. Arachidonsaeure

25. Immunocytophyt

26. Vevodar

27. Unii-27yg812j1i

28. Arachidonic-acid

29. Ccris 6312

30. 1adl

31. 1gnj

32. 1vyg

33. Einecs 208-033-4

34. Mfcd00004417

35. Ai3-09613

36. (14c)-arachidonic Acid

37. Spectrum5_001910

38. Arachidonic Acid, >97%

39. Schembl16162

40. Bspbio_001539

41. Mls001361328

42. Arachidonic Acid [mi]

43. (5z,8z,11z,14z)-5,8,11,14-eikosatetraensaeure

44. Bml3-b03

45. Gtpl2391

46. Arachidonic Acid [inci]

47. 5,8,11,14-eicosatetraenoate

48. Dtxsid4040420

49. Bdbm22319

50. Arachidonic Acid [mart.]

51. Arachidonic Acid [who-dd]

52. Chebi:137828

53. Hms1361m21

54. Hms1791m21

55. Hms1989m21

56. Hms3402m21

57. Hms3649b05

58. Zinc4474696

59. 5z,8z,11z,14z-eicosatetraenoate

60. Arachidonic Acid, >95.0% (gc)

61. 5,8,11,14-eicosatetraenoic Acid, Labeled With Carbon-14, (all-z)-

62. Arachidonic Acid, Analytical Standard

63. Cis-d5,8,11,14-eicosatetraenoate

64. Lmfa01030001

65. S6185

66. Akos015950830

67. Ccg-214838

68. Db04557

69. Fs-5880

70. 5,8,11,14-all-cis-eicosatetraenoate

71. All-cis-5,8,11,14-eicosatetraenoate

72. Arachidonic Acid (20:4 N-6)

73. Idi1_034009

74. Cis-d5,8,11,14-eicosatetraenoic Acid

75. Ncgc00094608-01

76. Ncgc00094608-02

77. Ncgc00094608-03

78. Ncgc00094608-04

79. Ncgc00094608-05

80. Ncgc00094608-06

81. (5z,8z,11z,14z)-icosatetraenoic Acid

82. (all-z)-5,8,11,14-eicosatetraenoate

83. 93444-49-6

84. Ac-14348

85. Ac-33769

86. Smr000857374

87. 5,8,11,14-all-cis-eicosatetraenoic Acid

88. Hy-109590

89. A0781

90. All-cis-eicosa-5,8,11,14-tetraenoic Acid

91. Cs-0032762

92. Cis-delta(5,8,11,14)-eicosatetraenoic Acid

93. 5-cis,8-cis,11-cis,14-cis-eicosatetraenoate

94. Arachidonic Acid (in Tocrisolvetrade Mark100)

95. C00219

96. W15452

97. Fa(20:4(5z,8z,11z,14z))

98. 5-cis,8-cis,11-cis,14-cis-eicosatetraenoic Acid

99. 506a321

100. A929392

101. Q407699

102. Sr-01000838311

103. Sr-01000838311-2

104. Brd-k03070961-001-02-8

105. Brd-k03070961-001-04-4

106. (5z,8z,11z,14z)-5,8,11,14-icosatetraenoic Acid

107. (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoicacid

108. (5z,8z,11z,14z)-5,8,11,14-icosatetraenoic Acid #

109. Arachidonic Acid, From Non-animal Source, >=98.5% (gc)

110. Arachidonic Acid, From Porcine Liver, >=99% (gc), Liquid

111. D18dbc10-379c-4e78-9a50-8b791a2f4e68

112. Arachidonic Acid, From Porcine Liver, >=85% (capillary Gc), Liquid

113. Arachidonic Acid, 1.0 Mg/ml In Ethanol, Certified Reference Material

114. Arachidonic Acid, From Porcine Liver, Bioreagent, Suitable For Cell Culture, >=99% (gc)

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₂O₂
Molecular Weight	304.5 g/mol
XLogP3	6.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	14
Exact Mass	304.240230259 g/mol
Monoisotopic Mass	304.240230259 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	362
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 Metabolism/Metabolites

Arachidonic acid has known human metabolites that include 10-HETE, 11,12-EET, 11-HETE, 12-HETE, 13-HETE, 14,15-EET, 15-HETE, 16-HETE, 17-HETE, 18-HETE, 19-HETE, 20-HETE, 5,6-EET, 5-HETE, 7-HETE, 8,9-EET, 8-HETE, and 9-HETE.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560