CHEBI:28364 - all-cis-5,8,11,14,17-icosapentaenoic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name all-cis-5,8,11,14,17-icosapentaenoic acid
ChEBI ID CHEBI:28364
ChEBI ASCII Name all-cis-5,8,11,14,17-icosapentaenoic acid
Definition An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42328, CHEBI:23901, CHEBI:4764
Supplier Information
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Formula C20H30O2
Net Charge 0
Average Mass 302.45100
Monoisotopic Mass 302.22458
InChI InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChIKey JAZBEHYOTPTENJ-JLNKQSITSA-N
SMILES CC\C=C/C\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
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
Mortierella alpina (NCBI:txid64518) 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): micronutrient
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
Daphnia galeata metabolite
A Daphnia metabolite produced by the species Daphnia galeata.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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 )
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(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.
anticholesteremic drug
A substance used to lower plasma cholesterol levels.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role Daphnia galeata metabolite (CHEBI:83038)
all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role anticholesteremic drug (CHEBI:35821)
all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role antidepressant (CHEBI:35469)
all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role antineoplastic agent (CHEBI:35610)
all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role fungal metabolite (CHEBI:76946)
all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role micronutrient (CHEBI:27027)
all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role mouse metabolite (CHEBI:75771)
all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role nutraceutical (CHEBI:50733)
all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) is a ω−3 fatty acid (CHEBI:25681)
all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) is a icosapentaenoic acid (CHEBI:36006)
all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) is conjugate acid of all-cis-5,8,11,14,17-icosapentaenoate (CHEBI:58562)
Incoming (5Z,11Z,14Z,17Z)-8,9-epoxyicosatetraenoic acid (CHEBI:137193) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
(5Z,8Z,11Z,14Z,16E,18R)-18-hydroperoxyicosapentaenoic acid (CHEBI:138565) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
(5Z,8Z,11Z,14Z,17Z)-icosapentaenoyl-containing glycerolipid (CHEBI:90083) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
(5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine (CHEBI:71467) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
(5Z,8Z,11Z,17Z)-14,15-epoxyicosatetraenoic acid (CHEBI:137269) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
(5Z,8Z,14Z,17Z)-11,12-epoxyicosatetraenoic acid (CHEBI:137267) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
(5Z,9E,11Z,14Z,17Z)-8-hydroperoxyicosapentaenoic acid (CHEBI:136656) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
(6E,8Z,11Z,14Z,17Z)-5-oxoicosapentaenoic acid (CHEBI:140244) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
1-[(11Z)-octadecenoyl]-2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86186) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
1-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86183) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
1-[(9Z)-octadecenoyl]-2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86187) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
1-hexadecanoyl-2-[(5Z,8Z,11Z,14Z,17Z)-icosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86137) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
1-hexadecyl-2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86437) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
1-icosanoyl-2-[(5Z,8Z,11ZZ,14Z,17Z)-eicosapentaenoyl]-sn-glycerol (CHEBI:87225) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
1-octadecanoyl-2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86181) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
11-HEPE (CHEBI:131889) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
12-HPEPE (CHEBI:78909) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
17(18)-EpETE (CHEBI:72853) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
19-HEPE (CHEBI:76959) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycerol (CHEBI:86398) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
20-HEPE (CHEBI:76962) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
5,20-diHEPE (CHEBI:130073) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
cholesteryl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoate) (CHEBI:84969) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate (CHEBI:84883) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
timnodonoyl bioconjugate (CHEBI:76189) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
all-cis-5,8,11,14,17-icosapentaenoate (CHEBI:58562) is conjugate base of all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
(5Z,8Z,11Z,14Z,17Z)-icosapentaenoyl group (CHEBI:85943) is substituent group from all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
IUPAC Name
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
INNs Sources
icosapent ChemIDplus
icosapento ChemIDplus
icosapentum ChemIDplus
Synonyms Sources
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid ChemIDplus
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate KEGG COMPOUND
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid KEGG COMPOUND
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid KEGG COMPOUND
(all-Z)-5,8,11,14,17-eicosapentaenoic acid ChemIDplus
5,8,11,14,17-EICOSAPENTAENOIC ACID PDBeChem
5,8,11,14,17-Icosapentaenoic acid KEGG COMPOUND
all-cis-5,8,11,14,17-eicosapentaenoic acid ChEBI
all-cis-icosa-5,8,11,14,17-pentaenoic acid ChEBI
cis, cis, cis, cis, cis-eicosa-5,8,11,14,17-pentaenoic acid ChEBI
cis-5,8,11,14,17-eicosapentaenoic acid ChemIDplus
cis-5,8,11,14,17-EPA ChEBI
cis-Δ5,8,11,14,17-eicosapentaenoic acid ChEBI
Eicosapentaenoic acid KEGG COMPOUND
Eicosapentaenoic acid KEGG COMPOUND
EPA DrugBank
Icosapentaenoic acid HMDB
Timnodonic acid DrugBank
Manual Xrefs Databases
3174 DrugCentral
C00000408 KNApSAcK
C00001215 KNApSAcK
C06428 KEGG COMPOUND
D08061 KEGG DRUG
DB00159 DrugBank
EICOSAPENTAENOATE MetaCyc
EPA PDBeChem
HMDB0001999 HMDB
LMFA01030759 LIPID MAPS
View more database links
Registry Numbers Types Sources
10417-94-4 CAS Registry Number KEGG COMPOUND
10417-94-4 CAS Registry Number ChemIDplus
1714433 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12549599 PubMed citation Europe PMC
18638380 PubMed citation Europe PMC
19054597 PubMed citation Europe PMC
21118482 PubMed citation Europe PMC
21274596 PubMed citation Europe PMC
23920312 PubMed citation Europe PMC
24108131 PubMed citation Europe PMC
24238887 PubMed citation Europe PMC
24387137 PubMed citation Europe PMC
24389665 PubMed citation Europe PMC
9668087 PubMed citation Europe PMC
Last Modified
05 March 2018