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CHEBI:28364 - all-cis-5,8,11,14,17-icosapentaenoic acid
| Formula | C20H30O2 |
| Net Charge | 0 |
| Average Mass | 302.458 |
| Monoisotopic Mass | 302.22458 |
| SMILES | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O |
| 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 |
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| 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: | 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. fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). 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. 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. 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. |
| 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 |
|---|---|
| icosapent | ChemIDplus |
| icosapento | ChemIDplus |
| icosapentum | ChemIDplus |
| Synonyms | Source |
|---|---|
| 5,8,11,14,17-EICOSAPENTAENOIC ACID | PDBeChem |
| 5,8,11,14,17-Icosapentaenoic acid | KEGG COMPOUND |
| (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 |
| 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 |
| Registry Numbers | Sources |
|---|---|
| Reaxys:1714433 | Reaxys |
| CAS:10417-94-4 | KEGG COMPOUND |
| CAS:10417-94-4 | ChemIDplus |
| Citations |
|---|