arachidonic acid (CHEBI:15843)

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CHEBI:15843 - arachidonic acid

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ChEBI Name	arachidonic acid

ChEBI ID	CHEBI:15843

Definition	A long-chain fatty acid that is a C₂₀, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40501, CHEBI:22608, CHEBI:2799

Supplier Information	ChemicalBook:CB8112259, eMolecules:478458, ZINC000004474696

Download	Molfile XML SDF

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36.5673 -25.5189 -0.4074 C 0 0 0 0 0 0 0 0 0 0 0 0

37.4159 -24.4042 0.2255 C 0 0 0 0 0 0 0 0 0 0 0 0

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41.4393 -23.0363 -2.2552 C 0 0 0 0 0 0 0 0 0 0 0 0

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39.5549 -26.7575 1.6658 C 0 0 0 0 0 0 0 0 0 0 0 0

35.7561 -26.1902 1.7187 O 0 0 0 0 0 0 0 0 0 0 0 0

36.3832 -27.8765 0.3862 O 0 0 0 0 0 0 0 0 0 0 0 0

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37.1460 -26.0164 -1.2211 H 0 0 0 0 0 0 0 0 0 0 0 0

38.3626 -24.8408 0.6226 H 0 0 0 0 0 0 0 0 0 0 0 0

36.8443 -23.9332 1.0597 H 0 0 0 0 0 0 0 0 0 0 0 0

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38.3276 -21.3767 0.3307 H 0 0 0 0 0 0 0 0 0 0 0 0

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45.4410 -23.8769 -2.5600 H 0 0 0 0 0 0 0 0 0 0 0 0

46.4062 -25.6456 -1.6183 H 0 0 0 0 0 0 0 0 0 0 0 0

43.8224 -26.3029 -0.0856 H 0 0 0 0 0 0 0 0 0 0 0 0

44.8913 -25.2889 0.9864 H 0 0 0 0 0 0 0 0 0 0 0 0

46.7567 -27.4191 0.1909 H 0 0 0 0 0 0 0 0 0 0 0 0

45.8643 -29.0868 1.3819 H 0 0 0 0 0 0 0 0 0 0 0 0

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43.6193 -28.8233 2.5993 H 0 0 0 0 0 0 0 0 0 0 0 0

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41.7008 -26.5031 1.9294 H 0 0 0 0 0 0 0 0 0 0 0 0

38.8905 -26.6025 0.7831 H 0 0 0 0 0 0 0 0 0 0 0 0

39.5035 -25.8635 2.3314 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 22 1 0 0 0 0

1 21 2 0 0 0 0

1 2 1 0 0 0 0

2 3 1 0 0 0 0

23 2 1 0 0 0 0

24 2 1 0 0 0 0

3 4 1 0 0 0 0

25 3 1 0 0 0 0

26 3 1 0 0 0 0

4 5 1 0 0 0 0

27 4 1 0 0 0 0

28 4 1 0 0 0 0

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29 5 1 0 0 0 0

6 7 1 0 0 0 0

30 6 1 0 0 0 0

7 8 1 0 0 0 0

31 7 1 0 0 0 0

32 7 1 0 0 0 0

8 9 2 0 0 0 0

33 8 1 0 0 0 0

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34 9 1 0 0 0 0

10 11 1 0 0 0 0

35 10 1 0 0 0 0

36 10 1 0 0 0 0

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37 11 1 0 0 0 0

12 13 1 0 0 0 0

38 12 1 0 0 0 0

13 14 1 0 0 0 0

39 13 1 0 0 0 0

40 13 1 0 0 0 0

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42 15 1 0 0 0 0

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52 20 1 0 0 0 0

53 20 1 0 0 0 0

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M END): 20 ms

reading 54 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

54 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile

Wikipedia	License
Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega−6 fatty acid 20:4(ω−6), or 20:4(5,8,11,14). If its precursors or diet contains linoleic acid it is formed by biosynthesis and can be deposited in animal fats. It is a precursor in the formation of leukotrienes, prostaglandins, and thromboxanes. Together with omega−3 fatty acids and other omega−6 fatty acids, arachidonic acid provides energy for body functions, contributes to cell membrane structure, and participates in the synthesis of eicosanoids, which have numerous roles in physiology as signaling molecules. Its name derives from the ancient Greek neologism arachis 'peanut', although peanut oil does not contain any arachidonic acid. Arachidonate is the name of the derived carboxylate anion (conjugate base of the acid), salts, and some esters.
Read full article at Wikipedia

Formula

C20H32O2

Net Charge

Average Mass

304.46690

Monoisotopic Mass

304.24023

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-

InChIKey

YZXBAPSDXZZRGB-DOFZRALJSA-N

SMILES

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	See: MetaboLights Study
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Daphnia galeata (NCBI:txid27404)	See: Is the fatty acid composition of Daphnia galeata determined by the fatty acid composition of the ingested diet?Weers P.M.M., Siewertsen K., and Gulati R.D.Freshwater Biology (1997), 38, 731-738

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	EC 3.1.1.1 (carboxylesterase) inhibitor Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of carboxylesterase (EC 3.1.1.1 ). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via icosatetraenoic acid ) Daphnia galeata metabolite A Daphnia metabolite produced by the species Daphnia galeata. Caenorhabditis elegans metabolite A nematode metabolite produced by Caenorhabditis elegans. (via icosatetraenoic acid )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	arachidonic acid (CHEBI:15843) has parent hydride (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraene (CHEBI:37834) arachidonic acid (CHEBI:15843) has role Daphnia galeata metabolite (CHEBI:83038) arachidonic acid (CHEBI:15843) has role EC 3.1.1.1 (carboxylesterase) inhibitor (CHEBI:78444) arachidonic acid (CHEBI:15843) has role human metabolite (CHEBI:77746) arachidonic acid (CHEBI:15843) has role mouse metabolite (CHEBI:75771) arachidonic acid (CHEBI:15843) is a ω−6 fatty acid (CHEBI:36009) arachidonic acid (CHEBI:15843) is a icosa-5,8,11,14-tetraenoic acid (CHEBI:36306) arachidonic acid (CHEBI:15843) is a long-chain fatty acid (CHEBI:15904) arachidonic acid (CHEBI:15843) is conjugate acid of arachidonate (CHEBI:32395)

Incoming	(5Z,8R,9R,11Z,14Z)-8,9-dihydroxyicosatrienoic acid (CHEBI:138586) has functional parent arachidonic acid (CHEBI:15843) (5Z,8S,9S,11Z,14Z)-8,9-dihydroxyicosatrienoic acid (CHEBI:138585) has functional parent arachidonic acid (CHEBI:15843) (5Z,8Z,11R,12R,14Z)-11,12-dihydroxyicosatrienoic acid (CHEBI:138593) has functional parent arachidonic acid (CHEBI:15843) (5Z,8Z,11S,12S,14Z)-11,12-dihydroxyicosatrienoic acid (CHEBI:138594) has functional parent arachidonic acid (CHEBI:15843) (5Z,8Z,11Z,14R,15R)-14,15-dihydroxyicosatrienoic acid (CHEBI:138591) has functional parent arachidonic acid (CHEBI:15843) (5Z,8Z,11Z,14S,15S)-14,15-dihydroxyicosatrienoic acid (CHEBI:138592) has functional parent arachidonic acid (CHEBI:15843) 1,2-diarachidonoyl-sn-glycerol (CHEBI:77125) has functional parent arachidonic acid (CHEBI:15843) 1-(1Z)-hexadecenyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:77292) has functional parent arachidonic acid (CHEBI:15843) 1-(1Z-hexadecenyl)-2-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:84527) has functional parent arachidonic acid (CHEBI:15843) 1-(1Z-octadecenyl)-2-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:79207) has functional parent arachidonic acid (CHEBI:15843) 1-(1Z-octadecenyl)-2-arachidonoyl-sn-glycero-3-phosphoserine (CHEBI:79211) has functional parent arachidonic acid (CHEBI:15843) 1-(1Z-octadecenyl)-sn-glycero-3-phospho-(N-arachidonoyl)ethanolamine (CHEBI:138096) has functional parent arachidonic acid (CHEBI:15843) 1-(9Z-octadecenyl)-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:85672) has functional parent arachidonic acid (CHEBI:15843) 1-O-alkyl-2-O-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:28894) has functional parent arachidonic acid (CHEBI:15843) 1-O-alkyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:76251) has functional parent arachidonic acid (CHEBI:15843) 1-O-arachidonoyl-N-acetylsphingosine (CHEBI:76080) has functional parent arachidonic acid (CHEBI:15843) 1-[(1Z)-octadecenyl]-2-[(5Z,8Z,11Z,14Z)-icosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84828) has functional parent arachidonic acid (CHEBI:15843) 1-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:86184) has functional parent arachidonic acid (CHEBI:15843) 1-[(7Z)-hexadecenoyl]-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:64505) has functional parent arachidonic acid (CHEBI:15843) 1-[(9Z)-hexadecenoyl]-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84816) has functional parent arachidonic acid (CHEBI:15843) 1-[(9Z)-octadecenyl]-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84827) has functional parent arachidonic acid (CHEBI:15843) 1-[(9Z)-tetradecenoyl]-2-[(5Z,8Z,11Z,14Z)-icosatetraenoyl]-sn-glycerol (CHEBI:86977) has functional parent arachidonic acid (CHEBI:15843) 1-[(9Z,12Z)-octadecadienoyl]-2-[(5Z,8Z,11Z,14Z)-icosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84563) has functional parent arachidonic acid (CHEBI:15843) 1-acyl-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:75112) has functional parent arachidonic acid (CHEBI:15843) 1-acyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:75063) has functional parent arachidonic acid (CHEBI:15843) 1-acyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:75067) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:75141) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoyl-2-oleoylglycerol (CHEBI:75611) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoyl-2-palmitoyl-sn-glycero-3-phosphocholine (CHEBI:77694) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:83053) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoyl-sn-glycero-3-phospho-L-serine (CHEBI:85435) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoyl-sn-glycero-3-phospho-L-serine(1−) (CHEBI:84723) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:74344) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:64395) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoyl-sn-glycerol 3-phosphate (CHEBI:73792) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoylglycerol (CHEBI:75612) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonoylglycerone 3-phosphate (CHEBI:78175) has functional parent arachidonic acid (CHEBI:15843) 1-heptadecanoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:84470) has functional parent arachidonic acid (CHEBI:15843) 1-heptadecanoyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85408) has functional parent arachidonic acid (CHEBI:15843) 1-heptadecanoyl-2-arachidonoyl-sn-glycero-3-phosphoserine (CHEBI:85400) has functional parent arachidonic acid (CHEBI:15843) 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-icosatetraenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:73117) has functional parent arachidonic acid (CHEBI:15843) 1-icosanoyl-2-arachidonoyl-sn-glycerol (CHEBI:87223) has functional parent arachidonic acid (CHEBI:15843) 1-oleoyl-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:75118) has functional parent arachidonic acid (CHEBI:15843) 1-oleoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:82762) has functional parent arachidonic acid (CHEBI:15843) 1-oleoyl-2-arachidonoyl-sn-glycero-3-phospho-L-serine (CHEBI:75099) has functional parent arachidonic acid (CHEBI:15843) 1-oleoyl-2-arachidonoyl-sn-glycerol (CHEBI:75449) has functional parent arachidonic acid (CHEBI:15843) 1-oleoyl-2-arachidonoyl-sn-glycerol-3-phosphoethanolamine (CHEBI:75169) has functional parent arachidonic acid (CHEBI:15843) 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-sn-glycerol) (CHEBI:84526) has functional parent arachidonic acid (CHEBI:15843) 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:73003) has functional parent arachidonic acid (CHEBI:15843) 1-palmitoyl-2-arachidonoyl-sn-glycerol (CHEBI:77096) has functional parent arachidonic acid (CHEBI:15843) 1-palmityl-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:77355) has functional parent arachidonic acid (CHEBI:15843) 1-palmityl-2-arachidonoyl-sn-glycerol (CHEBI:77184) has functional parent arachidonic acid (CHEBI:15843) 1-pentadecanoyl-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:86344) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoyl-3-oleoyl-sn-glycerol (CHEBI:75729) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol) (CHEBI:75646) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1D-myo-inositol 3,4,5-triphosphate) (CHEBI:83980) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:84153) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-biphosphate (CHEBI:77276) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 4-phosphate (CHEBI:77271) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate (CHEBI:77345) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:79110) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphoserine (CHEBI:79113) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoyl-sn-glycerol (CHEBI:75728) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoylglycerol (CHEBI:83288) has functional parent arachidonic acid (CHEBI:15843) 1-stearoyl-2-arachidonoylphosphatidic acid (CHEBI:84165) has functional parent arachidonic acid (CHEBI:15843) 1-tetradecanoyl-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:86102) has functional parent arachidonic acid (CHEBI:15843) 10-HETE (CHEBI:134453) has functional parent arachidonic acid (CHEBI:15843) 11,12-epoxy-20-hydroxy-(5Z,8Z,14Z)-icosatrienoic acid (CHEBI:138273) has functional parent arachidonic acid (CHEBI:15843) 13-HETE (CHEBI:137345) has functional parent arachidonic acid (CHEBI:15843) 14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoic acid (CHEBI:138274) has functional parent arachidonic acid (CHEBI:15843) 17,18-DiHETE (CHEBI:88349) has functional parent arachidonic acid (CHEBI:15843) 18(R)-HETE (CHEBI:91132) has functional parent arachidonic acid (CHEBI:15843) 19(S)-HETE (CHEBI:34185) has functional parent arachidonic acid (CHEBI:15843) 19-HETE (CHEBI:63998) has functional parent arachidonic acid (CHEBI:15843) 2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:79059) has functional parent arachidonic acid (CHEBI:15843) 2-arachidonoyl-sn-glycero-3-phospho-L-serine (CHEBI:78703) has functional parent arachidonic acid (CHEBI:15843) 2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:76079) has functional parent arachidonic acid (CHEBI:15843) 2-arachidonoyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:76091) has functional parent arachidonic acid (CHEBI:15843) 2-arachidonoylglycerol (CHEBI:52392) has functional parent arachidonic acid (CHEBI:15843) 2-arachidonyl-sn-glycero-3-phosphoethanolamine (CHEBI:72741) has functional parent arachidonic acid (CHEBI:15843) 20-HETE (CHEBI:34306) has functional parent arachidonic acid (CHEBI:15843) 20-oxoarachidonic acid (CHEBI:76965) has functional parent arachidonic acid (CHEBI:15843) 5,6-epoxy-20-hydroxy-(8Z,11Z,14Z)-icosatrienoic acid (CHEBI:138271) has functional parent arachidonic acid (CHEBI:15843) 7-HETE (CHEBI:137344) has functional parent arachidonic acid (CHEBI:15843) 8(S),15(S)-DiHETE (CHEBI:136485) has functional parent arachidonic acid (CHEBI:15843) 8(S),15(S)-DiHPETE (CHEBI:136400) has functional parent arachidonic acid (CHEBI:15843) 8,9-epoxy-20-hydroxy-(5Z,11Z,14Z)-icosatrienoic acid (CHEBI:138272) has functional parent arachidonic acid (CHEBI:15843) 9-oxo-ETE (CHEBI:136365) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoyl-γ-aminobutyric acid (CHEBI:132722) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85784) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85666) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoyl-2-oxoserotonin (CHEBI:132256) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85671) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoyl-L-alanine (CHEBI:132708) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoyl-L-leucine (CHEBI:136683) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoyl-L-phenylalanine (CHEBI:136606) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoyl-L-serine (CHEBI:143514) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoylglycine (CHEBI:58961) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoylphosphatidylethanolamine (CHEBI:52571) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoylphytosphingosine (CHEBI:85207) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoylserotonin (CHEBI:132255) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoylsphinganine (CHEBI:85206) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoylsphingosine (CHEBI:85198) has functional parent arachidonic acid (CHEBI:15843) N-arachidonoyltaurine (CHEBI:132506) has functional parent arachidonic acid (CHEBI:15843) AACOCF3 (CHEBI:2341) has functional parent arachidonic acid (CHEBI:15843) anandamide (CHEBI:2700) has functional parent arachidonic acid (CHEBI:15843) arachidonoyl amine (CHEBI:137830) has functional parent arachidonic acid (CHEBI:15843) arachidonoyl bioconjugate (CHEBI:76180) has functional parent arachidonic acid (CHEBI:15843) Arachidonoyl dopamine (CHEBI:31231) has functional parent arachidonic acid (CHEBI:15843) arachidonoyl-CoA (CHEBI:15514) has functional parent arachidonic acid (CHEBI:15843) arachidonoyl-containing glycerolipid (CHEBI:90077) has functional parent arachidonic acid (CHEBI:15843) arachidonoylcholine (CHEBI:133694) has functional parent arachidonic acid (CHEBI:15843) arachidonyl-2'-chloroethylamide (CHEBI:191854) has functional parent arachidonic acid (CHEBI:15843) CDP-1,2-diarachidonoyl-sn-glycerol (CHEBI:85835) has functional parent arachidonic acid (CHEBI:15843) CDP-1-palmitoyl-2-arachidonoyl-sn-glycerol (CHEBI:85830) has functional parent arachidonic acid (CHEBI:15843) CDP-1-stearoyl-2-arachidonoyl-sn-glycerol (CHEBI:85829) has functional parent arachidonic acid (CHEBI:15843) cholesteryl arachidonate (CHEBI:82751) has functional parent arachidonic acid (CHEBI:15843) DHET (CHEBI:64005) has functional parent arachidonic acid (CHEBI:15843) EET (CHEBI:64007) has functional parent arachidonic acid (CHEBI:15843) ethyl arachidonate (CHEBI:84873) has functional parent arachidonic acid (CHEBI:15843) lipoxin (CHEBI:6497) has functional parent arachidonic acid (CHEBI:15843) methyl arachidonate (CHEBI:78033) has functional parent arachidonic acid (CHEBI:15843) 1-arachidonyl-2-palmityl-sn-glycero-3-phosphocholine (CHEBI:77695) is a arachidonic acid (CHEBI:15843) arachidonate (CHEBI:32395) is conjugate base of arachidonic acid (CHEBI:15843)

IUPAC Name

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

Synonyms	Sources
(5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acid	NIST Chemistry WebBook
(5Z,8Z,11Z,14Z)-Icosatetraenoic acid	KEGG COMPOUND
AA	ChEBI
all-cis-5,8,11,14-eicosatetraenoic acid	ChEBI
ARA	ChEBI
Arachidonate	KEGG COMPOUND
Arachidonic acid	KEGG COMPOUND
ARACHIDONIC ACID	PDBeChem
Arachidonsäure	ChEBI
cis-5,8,11,14-Eicosatetraenoic acid	KEGG COMPOUND
cis-Δ^5,8,11,14-eicosatetraenoic acid	ChEBI

Manual Xrefs	Databases
ACD	PDBeChem
Arachidonic_acid	Wikipedia
ARACHIDONIC_ACID	MetaCyc
C00000388	KNApSAcK
C00219	KEGG COMPOUND
DB04557	DrugBank
HMDB0001043	HMDB
LMFA01030001	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
1913991	Reaxys Registry Number	Reaxys
506-32-1	CAS Registry Number	KEGG COMPOUND
506-32-1	CAS Registry Number	ChemIDplus
506-32-1	CAS Registry Number	NIST Chemistry WebBook
58972	Gmelin Registry Number	Gmelin

Citations

Bourgeois EA, Subramaniam S, Cheng TY, De Jong A, Layre E, Ly D, Salimi M, Legaspi A, Modlin RL, Salio M, Cerundolo V, Moody DB, Ogg G (2015)
Bee venom processes human skin lipids for presentation by CD1a.
The Journal of experimental medicine 212, 149-163 [PubMed:25584012]
[show Abstract]

Agostoni C (2008)
Role of long-chain polyunsaturated fatty acids in the first year of life.
Journal of pediatric gastroenterology and nutrition 47 Suppl 2, S41-4 [PubMed:18931599]
[show Abstract]

Rapoport SI (2008)
Brain arachidonic and docosahexaenoic acid cascades are selectively altered by drugs, diet and disease.
Prostaglandins, leukotrienes, and essential fatty acids 79, 153-156 [PubMed:18973997]
[show Abstract]

Bourre JM (2004)
Roles of unsaturated fatty acids (especially omega-3 fatty acids) in the brain at various ages and during ageing.
The journal of nutrition, health & aging 8, 163-174 [PubMed:15129302]
[show Abstract]
Among various organs, in the brain, the fatty acids most extensively studied are omega-3 fatty acids. Alpha-linolenic acid (18:3omega3) deficiency alters the structure and function of membranes and induces minor cerebral dysfunctions, as demonstrated in animal models and subsequently in human infants. Even though the brain is materially an organ like any other, that is to say elaborated from substances present in the diet (sometimes exclusively), for long it was not accepted that food can have an influence on brain structure, and thus on its function. Lipids, and especially omega-3 fatty acids, provided the first coherent experimental demonstration of the effect of diet (nutrients) on the structure and function of the brain. In fact the brain, after adipose tissue, is the organ richest in lipids, whose only role is to participate in membrane structure. First it was shown that the differentiation and functioning of cultured brain cells requires not only alpha-linolenic acid (the major component of the omega-3, omega3 family), but also the very long omega-3 and omega-6 carbon chains (1). It was then demonstrated that alpha-linolenic acid deficiency alters the course of brain development, perturbs the composition and physicochemical properties of brain cell membranes, neurones, oligodendrocytes, and astrocytes (2). This leads to physicochemical modifications, induces biochemical and physiological perturbations, and results in neurosensory and behavioural upset (3). Consequently, the nature of polyunsaturated fatty acids (in particular omega-3) present in formula milks for infants (premature and term) conditions the visual and cerebral abilities, including intellectual. Moreover, dietary omega-3 fatty acids are certainly involved in the prevention of some aspects of cardiovascular disease (including at the level of cerebral vascularization), and in some neuropsychiatric disorders, particularly depression, as well as in dementia, notably Alzheimer's disease. Recent results have shown that dietary alpha-linolenic acid deficiency induces more marked abnormalities in certain cerebral structures than in others, as the frontal cortex and pituitary gland are more severely affected. These selective lesions are accompanied by behavioural disorders more particularly affecting certain tests (habituation, adaptation to new situations). Biochemical and behavioural abnormalities are partially reversed by a dietary phospholipid supplement, especially omega-3-rich egg yolk extracts or pig brain. A dose-effect study showed that animal phospholipids are more effective than plant phospholipids to reverse the consequences of alpha-linolenic acid deficiency, partly because they provide very long preformed chains. Alpha-linolenic acid deficiency decreases the perception of pleasure, by slightly altering the efficacy of sensory organs and by affecting certain cerebral structures. Age-related impairment of hearing, vision and smell is due to both decreased efficacy of the parts of the brain concerned and disorders of sensory receptors, particularly of the inner ear or retina. For example, a given level of perception of a sweet taste requires a larger quantity of sugar in subjects with alpha-linolenic acid deficiency. In view of occidental eating habits, as omega-6 fatty acid deficiency has never been observed, its impact on the brain has not been studied. In contrast, omega-9 fatty acid deficiency, specifically oleic acid deficiency, induces a reduction of this fatty acid in many tissues, except the brain (but the sciatic nerve is affected). This fatty acid is therefore not synthesized in sufficient quantities, at least during pregnancy-lactation, implying a need for dietary intake. It must be remembered that organization of the neurons is almost complete several weeks before birth, and that these neurons remain for the subject's life time. Consequently, any disturbance of these neurons, an alteration of their connections, and impaired turnover of their constituents at any stage of life, will tend to accelerate ageing. The enzymatic activities of sytivities of synthesis of long-chain polyunsaturated fatty acids from linoleic and alpha-linolenic acids are very limited in the brain: this organ therefore depends on an exogenous supply. Consequently, fatty acids that are essential for the brain are arachidonic acid and cervonic acid, derived from the diet, unless they are synthesized by the liver from linoleic acid and alpha-linolenic acid. The age-related reduction of hepatic desaturase activities (which participate in the synthesis of long chains, together with elongases) can impair turnover of cerebral membranes. In many structures, especially in the frontal cortex, a reduction of cervonic and arachidonic acids is observed during ageing, predominantly associated with a reduction of phosphatidylethanolamines (mainly in the form of plasmalogens). Peroxisomal oxidation of polyunsaturated fatty acids decreases in the brain during ageing, participating in decreased turnover of membrane fatty acids, which are also less effectively protected against peroxidation by free radicals.

Samuelsson B, Dahlén SE, Lindgren JA, Rouzer CA, Serhan CN (1987)
Leukotrienes and lipoxins: structures, biosynthesis, and biological effects.
Science (New York, N.Y.) 237, 1171-1176 [PubMed:2820055]
[show Abstract]

Last Modified

27 May 2022

General Comments
2011-03-24	It is one of the essential fatty acids required by most mammals, and the counterpart to the saturated arachidic acid found in peanut oil.
2011-03-24	Released from membrane phospholipids upon cell stimulation, arachidonic acid is converted by a 5-lipoxygenase to leukotrienes, which participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation.

CHEBI:15843 - arachidonic acid

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