CHEBI:53487 - all-cis-docosa-7,10,13,16-tetraenoic acid

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ChEBI Name all-cis-docosa-7,10,13,16-tetraenoic acid
ChEBI ID CHEBI:53487
ChEBI ASCII Name all-cis-docosa-7,10,13,16-tetraenoic acid
Definition The all-cis-isomer of a C22 polyunsaturated fatty acid having four double bonds in the 7-, 10-, 13- and 16-positions. One of the most abundant fatty acids in the early human brain.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Steve Jupe
Supplier Information eMolecules:537269, ZINC000004543724
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Docosatetraenoic acid designates any straight chain 22:4 fatty acid. (See Essential fatty acid for nomenclature.) One isomer is of particular interest: all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the common name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins, and epoxydocosatrienoic acids (EDTs, also known as dihomo-EETs). In addition to being endothelium-derived hyperpolarizing factors, EDTs have demonstrated anti-endoplasmic reticulum stress and anti-nociceptive activities. They are hydrolyzed by the soluble epoxide hydrolase (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors.
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Formula C22H36O2
Net Charge 0
Average Mass 332.521
Monoisotopic Mass 332.27153
InChI InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-
InChIKey TWSWSIQAPQLDBP-DOFZRALJSA-N
SMILES C(=C\C/C=C\C/C=C\CCCCCC(O)=O)\C/C=C\CCCCC
Metabolite of Species Details
Rebecca salina (NCBI:txid561169) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
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).
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.
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ChEBI Ontology
Outgoing all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487) has role algal metabolite (CHEBI:84735)
all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487) has role human metabolite (CHEBI:77746)
all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487) is a ω−6 fatty acid (CHEBI:36009)
all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487) is a docosatetraenoic acid (CHEBI:61205)
all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487) is conjugate acid of all-cis-docosa-7,10,13,16-tetraenoate (CHEBI:77225)
Incoming (7Z,10Z,13Z,16Z)-docosatetraenoyl-CoA (CHEBI:63544) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
(7Z,10Z,13Z,16Z)-docosatetraenoyl-containing glycerolipid (CHEBI:88264) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1,2-di-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerol (CHEBI:84440) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-(all-cis-docosa-7,10,13,16-tetraenoyl)glycerol (CHEBI:142499) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86200) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:133657) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-[(9Z)-octadecenoyl]-2-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:86201) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-hexadecanoyl-2-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84573) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-icosyl-2-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:86452) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-octadecanoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphocholine (CHEBI:84565) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-octadecyl-2-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:86447) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-oleoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerol (CHEBI:84438) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-palmitoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:84549) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-palmitoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerol (CHEBI:84405) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-stearoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoserine (CHEBI:84506) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
1-stearoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerol (CHEBI:84435) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
CE(22:4(7Z,10Z,13Z,16Z)) (CHEBI:142698) has functional parent all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
all-cis-docosa-7,10,13,16-tetraenoate (CHEBI:77225) is conjugate base of all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
(7Z,10Z,13Z,16Z)-docosatetraenoyl group (CHEBI:85929) is substituent group from all-cis-docosa-7,10,13,16-tetraenoic acid (CHEBI:53487)
IUPAC Name
(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acid
Synonyms Sources
(7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid KEGG COMPOUND
7,10,13,16-Docosatetraenoic acid KEGG COMPOUND
7Z,10Z,13Z,16Z-docosatetraenoic acid LIPID MAPS
adrenic acid SUBMITTER
Adrenic acid KEGG COMPOUND
all-cis-7,10,13,16-docosatetraenoic acid ChEBI
cis,cis,cis,cis-Docosa-7,10,13,16-tetraensäure ChEBI
Manual Xrefs Databases
C16527 KEGG COMPOUND
Docosatetraenoic_acid Wikipedia
HMDB0002226 HMDB
LMFA01030178 LIPID MAPS
View more database links
Registry Numbers Types Sources
1914611 Reaxys Registry Number Reaxys
28874-58-0 CAS Registry Number KEGG COMPOUND
28874-58-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
02 September 2024
General Comment
2011-02-03 A naturally occurring polyunsaturated fatty acid formed through a 2-C chain elongation of arachidonic acid, it is one of the most abundant fatty acids in the early human brain --Wikipedia.