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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: | immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. 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. antiviral agent A substance that destroys or inhibits replication of viruses. 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. anti-obesity agent Any substance which is used to reduce or control weight. bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. 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). |
| Applications: | antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. cardiovascular drug A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume. anticonvulsant A drug used to prevent seizures or reduce their severity. gastrointestinal drug A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion. immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. anticholesteremic drug A substance used to lower plasma cholesterol levels. renoprotective agent Any compound that is able to prevent damage to the kidneys. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. antipsychotic agent Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. antirheumatic drug A drug used to treat rheumatoid arthritis. anti-inflammatory agent Any compound that has anti-inflammatory effects. anti-asthmatic agent Any compound that has anti-asthmatic effects. 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. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. |
| 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 anti-asthmatic agent (CHEBI:65023) |
| all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role anti-inflammatory agent (CHEBI:67079) |
| all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role anti-obesity agent (CHEBI:74518) |
| 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 anticonvulsant (CHEBI:35623) |
| 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 antipsychotic agent (CHEBI:35476) |
| all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role antirheumatic drug (CHEBI:35842) |
| all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role antiviral agent (CHEBI:22587) |
| all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role cardiovascular drug (CHEBI:35554) |
| 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 gastrointestinal drug (CHEBI:55324) |
| all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role geroprotector (CHEBI:176497) |
| all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364) has role immunosuppressive agent (CHEBI:35705) |
| 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) has role renoprotective agent (CHEBI:231911) |
| 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 |
|---|