CHEBI:28125 - all-cis-docosa-4,7,10,13,16,19-hexaenoic acid

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ChEBI Name all-cis-docosa-4,7,10,13,16,19-hexaenoic acid
ChEBI ID CHEBI:28125
ChEBI ASCII Name all-cis-docosa-4,7,10,13,16,19-hexaenoic acid
Definition A docosahexaenoic acid having six cis-double bonds at positions 4, 7, 10, 13, 16 and 19.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43162, CHEBI:4673, CHEBI:23857
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Formula C22H32O2
Net Charge 0
Average Mass 328.48830
Monoisotopic Mass 328.240
InChI InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChIKey MBMBGCFOFBJSGT-KUBAVDMBSA-N
SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:10090) See: MetaboLights Study
Daphnia tenebrosa (NCBI:521141) See: Trophic transfer and trophic modification of fatty acids in high Arctic lakesHessen D., Liu E.Freshwater Biology (2006) 51, 1987-1998
Rebecca salina (NCBI:561169) See: PubMed
Homo sapiens (NCBI:9606) See: PubMed
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): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via docosahexaenoic acid )
(via omega-3 fatty acid )
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Daphnia tenebrosa metabolite
A Daphnia metabolite produced by the species Daphnia tenebrosa.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
(via omega-3 fatty acid )
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via omega-3 fatty acid )
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via omega-3 fatty acid )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125) has role Daphnia tenebrosa metabolite (CHEBI:83146)
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125) has role algal metabolite (CHEBI:84735)
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125) has role antineoplastic agent (CHEBI:35610)
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125) has role human metabolite (CHEBI:77746)
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125) has role mouse metabolite (CHEBI:75771)
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125) has role nutraceutical (CHEBI:50733)
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125) is a ω−3 fatty acid (CHEBI:25681)
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125) is a docosahexaenoic acid (CHEBI:36005)
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125) is conjugate acid of (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate (CHEBI:77016)
Incoming (17S)-HPDoHE (CHEBI:136113) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,13Z,15E,17R,19Z)-17-hydroperoxydocosahexaenoic acid (CHEBI:138590) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,13Z,16Z)-19,20-epoxydocosapentaenoic acid (CHEBI:72653) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,13Z,16Z,19R,20S)-19,20-epoxydocosapentaenoic acid (CHEBI:137154) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,13Z,16Z,19S,20R)-19,20-epoxydocosapentaenoic acid (CHEBI:137183) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,13Z,16Z,19Z)-22-hydroxydocosahexaenoic acid (CHEBI:77124) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA (CHEBI:65132) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-containing glycerolipid (CHEBI:88267) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,13Z,19Z)-16,17-epoxydocosapentaenoic acid (CHEBI:72855) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,16Z,19Z)-13,14-epoxydocosapentaenoic acid (CHEBI:136563) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,11E,13Z,16Z,19Z)-10-hydroperoxydocosahexaenoic acid (CHEBI:136657) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,11Z,13Z,15E,17S,19Z)-10,17-bis(hydroperoxy)docosahexaenoic acid (CHEBI:136587) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,13Z,16Z,19Z)-10,11-epoxydocosapentaenoic acid (CHEBI:136569) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:84538) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1,2-di[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphate (CHEBI:83778) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1,2-di[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycerol (CHEBI:82925) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-(1Z,9Z-octadecadienyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:90487) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-(1Z-hexadecenyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:90479) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-(1Z-octadecenyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:79099) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-(1Z-octadecenyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoserine (CHEBI:79102) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine (CHEBI:73873) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-O-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-N-acetylsphingosine (CHEBI:76087) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-[(11Z)-octadecenoyl]-2-[(4Z,7Z,10Z,13Z,16Z,19Z)]-docosahexaenoyl-sn-glycero-3-phosphocholine (CHEBI:84812) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-2-hexadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86182) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-[(6Z,9Z,12Z,15Z)-octadecatetraenoyl]-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycerol (CHEBI:87246) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-[(9Z)-octadecenoyl]-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphocholine (CHEBI:84814) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-eicosanoyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86221) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine (CHEBI:74963) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:79097) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoserine (CHEBI:79103) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-hexadecyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86248) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine (CHEBI:84829) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:79109) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoserine (CHEBI:79098) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-octadecyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86252) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-oleoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol (CHEBI:84439) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-palmitoyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphate (CHEBI:83785) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-palmitoyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycerol (CHEBI:82949) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-stearoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycero-3-phosphate (CHEBI:77258) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-stearoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycerol (CHEBI:77129) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
1-tetradecanoyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86162) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
14(S)-HPDHE (CHEBI:78861) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
14-HPDHE (CHEBI:84177) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycero-3-phosphocholine (CHEBI:76085) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
21-HDoHE (CHEBI:132325) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
N-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85780) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
N-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoylethanolamine (CHEBI:85252) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
N-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-L-glutamic acid (CHEBI:132485) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
CDP-1-stearoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycerol (CHEBI:85846) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
cholesteryl (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate (CHEBI:74102) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
ethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate (CHEBI:84945) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
lysophosphatidylethanolamine (0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (CHEBI:72749) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
lysophosphatidylethanolamine (22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) (CHEBI:72747) has functional parent all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate (CHEBI:77016) is conjugate base of all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl group (CHEBI:85932) is substituent group from all-cis-docosa-4,7,10,13,16,19-hexaenoic acid (CHEBI:28125)
IUPAC Name
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
Synonyms Sources
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid KEGG COMPOUND
22:6(n-3) ChEBI
22:6-4, 7,10,13,16,19 ChEBI
4,7,10,13,16,19-docosahexaenoic acid ChEBI
4,7,10,13,16,19-Docosahexaenoic acid KEGG COMPOUND
all-cis-4,7,10,13,16,19-docosahexaenoic acid ChEBI
all-cis-DHA ChEBI
cervonic acid ChEBI
DHA ChEBI
Doconexent ChemIDplus
DOCOSA-4,7,10,13,16,19-HEXAENOIC ACID PDBeChem
docosa-4,7,10,13,16,19-hexaenoic acid ChEBI
Docosahexaenoic acid KEGG COMPOUND
Docosahexaenoic acid KEGG COMPOUND
Database Links Databases
4289 DrugCentral
C06429 KEGG COMPOUND
CPD-10244 MetaCyc
DB03756 DrugBank
Docosahexaenoic_acid Wikipedia
HMDB0002183 HMDB
HXA PDBeChem
LMFA01030185 LIPID MAPS
View more database links
Registry Numbers Types Sources
1715505 Reaxys Registry Number Reaxys
1715505 Beilstein Registry Number Beilstein
6217-54-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12359365 PubMed citation Europe PMC
12538082 PubMed citation Europe PMC
17291553 PubMed citation Europe PMC
18072818 PubMed citation Europe PMC
18220672 PubMed citation Europe PMC
21045096 PubMed citation Europe PMC
Last Modified
07 December 2017
General Comment
2011-03-29 The most abundant omega-3 fatty acid in the brain and retina, its deficiency is associated with cognitive decline. It is also known to reduce the incidence and severity of a number of diseases.