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CHEBI:15843 - arachidonic acid

ChEBI IDCHEBI:15843
ChEBI Namearachidonic acid
Stars
DefinitionA long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14.
Secondary ChEBI IDsCHEBI:2799, CHEBI:22608, CHEBI:40501
Last Modified27 May 2022
DownloadsMolfile
FormulaC20H32O2
Net Charge0
Average Mass304.474
Monoisotopic Mass304.24023
SMILESCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChIInChI=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-
InChIKeyYZXBAPSDXZZRGB-DOFZRALJSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Daphnia galeata (ncbitaxon:27404) - Article (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)
Mus musculus (ncbitaxon:10090)
- MetaboLights (MTBLS143)
- PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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 ).
Daphnia galeata metabolite  A Daphnia metabolite produced by the species Daphnia galeata.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Caenorhabditis elegans metabolite  A nematode metabolite produced by Caenorhabditis elegans.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
ChEBI Ontology
Outgoing Relation(s)
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 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 a ω−6 fatty acid (CHEBI:36009)
arachidonic acid (CHEBI:15843) is conjugate acid of arachidonate (CHEBI:32395)
Incoming Relation(s)
(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)
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-arachidonoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85666) 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-2-oxoserotonin (CHEBI:132256) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-γ-aminobutyric acid (CHEBI:132722) 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)
1-(1Z-hexadecenyl)-2-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:84527) 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-(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)-hexadecenyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:77292) 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-[(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,12Z)-octadecadienoyl]-2-[(5Z,8Z,11Z,14Z)-icosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84563) 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-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-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-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-phospho-1D-myo-inositol (CHEBI:83053) 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-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-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-L-serine (CHEBI:75099) 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-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-sn-glycero-3-phospho-(1'-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 4-phosphate (CHEBI:77271) 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 5-phosphate (CHEBI:77345) 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-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-arachidonoyl-3-oleoyl-sn-glycerol (CHEBI:75729) 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)
1,2-diarachidonoyl-sn-glycerol (CHEBI:77125) 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-HETE (CHEBI:63998) has functional parent arachidonic acid (CHEBI:15843)
19(S)-HETE (CHEBI:34185) 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)
8,9-epoxy-20-hydroxy-(5Z,11Z,14Z)-icosatrienoic acid (CHEBI:138272) 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)
9-oxo-ETE (CHEBI:136365) 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-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)
CDP-1,2-diarachidonoyl-sn-glycerol (CHEBI:85835) 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  Source
Arachidonic acidKEGG COMPOUND
cis-5,8,11,14-Eicosatetraenoic acidKEGG COMPOUND
(5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acidNIST Chemistry WebBook
cis-Δ5,8,11,14-eicosatetraenoic acidChEBI
all-cis-5,8,11,14-eicosatetraenoic acidChEBI
ArachidonsäureChEBI
Manual XrefsDatabases
C00219KEGG COMPOUND
LMFA01030001LIPID MAPS
ACDPDBeChem
DB04557DrugBank
ARACHIDONIC_ACIDMetaCyc
HMDB0001043HMDB
Arachidonic_acidWikipedia
C00000388KNApSAcK
Registry NumbersSources
Gmelin:58972Gmelin
Reaxys:1913991Reaxys
CAS:506-32-1KEGG COMPOUND
CAS:506-32-1ChemIDplus
CAS:506-32-1NIST Chemistry WebBook
Citations