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:CB3249347, eMolecules:594677

Download	Molfile XML SDF

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54 53 0 0 0 0 999 V2000

36.2091 -26.5468 0.6486 C 0 0 0 0 0 0 0 0 0 0 0 0

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

37.7493 -23.3367 -0.8332 C 0 0 0 0 0 0 0 0 0 0 0 0

38.6640 -22.2831 -0.2257 C 0 0 0 0 0 0 0 0 0 0 0 0

40.0061 -22.3813 -0.3255 C 0 0 0 0 0 0 0 0 0 0 0 0

40.6567 -23.5485 -1.0560 C 0 0 0 0 0 0 0 0 0 0 0 0

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

42.7867 -23.0932 -2.2843 C 0 0 0 0 0 0 0 0 0 0 0 0

43.5900 -23.6747 -1.1286 C 0 0 0 0 0 0 0 0 0 0 0 0

44.8826 -24.2605 -1.6737 C 0 0 0 0 0 0 0 0 0 0 0 0

45.4701 -25.3305 -1.0998 C 0 0 0 0 0 0 0 0 0 0 0 0

44.8751 -26.0025 0.1290 C 0 0 0 0 0 0 0 0 0 0 0 0

45.6948 -27.2381 0.4807 C 0 0 0 0 0 0 0 0 0 0 0 0

45.1574 -28.2428 1.2025 C 0 0 0 0 0 0 0 0 0 0 0 0

43.7225 -28.1759 1.6968 C 0 0 0 0 0 0 0 0 0 0 0 0

42.7567 -28.6628 0.5995 C 0 0 0 0 0 0 0 0 0 0 0 0

41.3027 -28.4614 1.0550 C 0 0 0 0 0 0 0 0 0 0 0 0

41.0012 -26.9575 1.1887 C 0 0 0 0 0 0 0 0 0 0 0 0

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

35.6300 -25.0850 -0.8288 H 0 0 0 0 0 0 0 0 0 0 0 0

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

36.8092 -22.8484 -1.1831 H 0 0 0 0 0 0 0 0 0 0 0 0

38.2651 -23.8149 -1.6991 H 0 0 0 0 0 0 0 0 0 0 0 0

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

40.5493 -21.5421 0.1696 H 0 0 0 0 0 0 0 0 0 0 0 0

39.8661 -24.2540 -1.4049 H 0 0 0 0 0 0 0 0 0 0 0 0

41.3499 -24.0797 -0.3620 H 0 0 0 0 0 0 0 0 0 0 0 0

40.9951 -22.5885 -3.1753 H 0 0 0 0 0 0 0 0 0 0 0 0

43.2188 -22.6769 -3.2247 H 0 0 0 0 0 0 0 0 0 0 0 0

42.9986 -24.4765 -0.6268 H 0 0 0 0 0 0 0 0 0 0 0 0

43.8254 -22.8698 -0.3930 H 0 0 0 0 0 0 0 0 0 0 0 0

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

43.4805 -27.1207 1.9660 H 0 0 0 0 0 0 0 0 0 0 0 0

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

42.9350 -29.7463 0.4029 H 0 0 0 0 0 0 0 0 0 0 0 0

42.9343 -28.0806 -0.3356 H 0 0 0 0 0 0 0 0 0 0 0 0

41.1524 -28.9588 2.0422 H 0 0 0 0 0 0 0 0 0 0 0 0

40.6137 -28.9121 0.3021 H 0 0 0 0 0 0 0 0 0 0 0 0

41.1351 -26.4626 0.1978 H 0 0 0 0 0 0 0 0 0 0 0 0

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

39.2209 -27.6614 2.2282 H 0 0 0 0 0 0 0 0 0 0 0 0

36.7511 -28.1729 -0.5134 H 0 0 0 0 0 0 0 0 0 0 0 0

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

5 6 2 0 0 0 0

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

9 10 1 0 0 0 0

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

11 12 2 0 0 0 0

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

14 15 2 0 0 0 0

41 14 1 0 0 0 0

15 16 1 0 0 0 0

42 15 1 0 0 0 0

16 17 1 0 0 0 0

43 16 1 0 0 0 0

44 16 1 0 0 0 0

17 18 1 0 0 0 0

45 17 1 0 0 0 0

46 17 1 0 0 0 0

18 19 1 0 0 0 0

47 18 1 0 0 0 0

48 18 1 0 0 0 0

19 20 1 0 0 0 0

49 19 1 0 0 0 0

50 19 1 0 0 0 0

51 20 1 0 0 0 0

52 20 1 0 0 0 0

53 20 1 0 0 0 0

54 22 1 0 0 0 0

M END): 17 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

Script completed

Jmol script terminated

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Molfile

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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	Types	Sources
15129302	PubMed citation	Europe PMC
18931599	PubMed citation	Europe PMC
18973997	PubMed citation	Europe PMC
25584012	PubMed citation	Europe PMC
2820055	PubMed citation	Europe PMC

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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