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

Default Structure
ChEBI IDCHEBI:28364
ChEBI Nameall-cis-5,8,11,14,17-icosapentaenoic acid
Stars
ASCII Nameall-cis-5,8,11,14,17-icosapentaenoic acid
DefinitionAn icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.
Secondary ChEBI IDsCHEBI:4764, CHEBI:23901, CHEBI:42328
Last Modified5 March 2018
DownloadsMolfile
FormulaC20H30O2
Net Charge0
Average Mass302.458
Monoisotopic Mass302.22458
SMILESCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChIInChI=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-
InChIKeyJAZBEHYOTPTENJ-JLNKQSITSA-N
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)
Mortierella alpina (ncbitaxon:64518) - PubMed (9668087)
Mus musculus (ncbitaxon:10090) - MetaboLights (MTBLS143)
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:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
micronutrient  Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Daphnia galeata metabolite  A Daphnia metabolite produced by the species Daphnia galeata.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Applications:
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.
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
ChEBI Ontology
Outgoing Relation(s)
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 icosapentaenoic acid (CHEBI:36006)
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 conjugate acid of all-cis-5,8,11,14,17-icosapentaenoate (CHEBI:58562)
Incoming Relation(s)
(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  Source
icosapentChemIDplus
icosapentoChemIDplus
icosapentumChemIDplus
Synonyms  Source
5,8,11,14,17-EICOSAPENTAENOIC ACIDPDBeChem
5,8,11,14,17-Icosapentaenoic acidKEGG COMPOUND
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acidChemIDplus
(5Z,8Z,11Z,14Z,17Z)-EicosapentaenoateKEGG COMPOUND
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acidKEGG COMPOUND
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acidKEGG COMPOUND
Manual XrefsDatabases
3174DrugCentral
C00000408KNApSAcK
C00001215KNApSAcK
C06428KEGG COMPOUND
D08061KEGG DRUG
DB00159DrugBank
EICOSAPENTAENOATEMetaCyc
EPAPDBeChem
HMDB0001999HMDB
LMFA01030759LIPID MAPS
Registry NumbersSources
Reaxys:1714433Reaxys
CAS:10417-94-4KEGG COMPOUND
CAS:10417-94-4ChemIDplus
Citations