Icosapent
PubChem CID: 446284
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| Compound Synonyms | Eicosapentaenoic acid, Timnodonic acid, Icosapent, 10417-94-4, Icosapentaenoic acid, EPA, cis-5,8,11,14,17-Eicosapentaenoic acid, Icosapento, 5,8,11,14,17-EICOSAPENTAENOIC ACID, Icosapentum, (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid, Miraxion, eicosapentaenoate, 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid, (all-Z)-5,8,11,14,17-Eicosapentaenoic acid, Icosapent [INN], Eicosapentanoic acid, (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid, Eye Q, Eye-Q, Ropufa 70, Incromega e 7010sr, CCRIS 3279, AAN7QOV9EA, UNII-AAN7QOV9EA, EPA 45G, (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid, 5,8,11,14,17-Icosapentaenoic acid, EPA [drug], CHEBI:28364, (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate, (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid, Icosapentum [INN-Latin], MFCD00065716, Icosapento [INN-Spanish], C20:5n-3,6,9,12,15, C20:5 (n-3), CHEMBL460026, DTXSID9041023, all-cis-5,8,11,14,17-icosapentaenoic acid, all-cis-5,8,11,14,17-eicosapentaenoic acid, all-cis-icosa-5,8,11,14,17-pentaenoic acid, Icosapent (INN), cis-Delta(5,8,11,14,17)-eicosapentaenoic acid, 5,8,11,14,17-Eicosapentaenoic acid, (all-Z)-, Eicosapentaenoic acid (c20:5 n3), EPA, Timnodonic acid, Icosapentaenoate, (all-Z)-delta5,8,11,14,17-Eicosapentaenoic acid, EPA (drug), cis-5,8,11,14,17-EPA, FA 20:5, NCGC00161344-03, 5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-, EICOSAPENTAENOIC ACID (20:5 n-3), Icosapentum (INN-Latin), Icosapento (INN-Spanish), all cis-5,8,11,14,17-Eicosapentaenoic Acid, (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate, Timnodonate, 3gwx, RELIVEN, EPA-FFA, all-cis-icosapentaenoate, ICOSAPENT (EPA), all-cis-icosapentaenoic acid, SCHEMBL20469, BSPBio_001328, BML3-B01, GTPL3362, DTXCID7021023, Eicosapentaenoic Acid (Standard), HY-B0660R, EICOSAPENTAENOIC ACID [MI], HMS1361C10, HMS1791C10, HMS1989C10, HMS3402C10, HMS3649D19, HY-B0660, 5,8,11,14,17-Icosapentaenoate, Tox21_111991, 5,8,11,14,17-Eicosapentaenoate, BDBM50242349, EICOSAPENTAENOIC ACID [VANDF], LMFA01030759, s6476, EICOSAPENTAENOIC ACID [MART.], AKOS027470327, EICOSAPENTAENOIC ACID [USP-RS], EICOSAPENTAENOIC ACID [WHO-DD], CCG-207957, CCG-208136, DB00159, FE22647, cis-5,8,11,14,17-eicosapentaenoate, IDI1_033798, NCGC00161344-01, NCGC00161344-02, NCGC00161344-04, NCGC00161344-07, 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate, AC-31072, AS-53730, CAS-10417-94-4, E0441, NS00010730, 5,8,11,14,17-Eicosapentaenoic acid (6CI), all cis-5,8,11,14,17-Icosapentaenoic Acid, C06428, D08061, P16966, EN300-7403855, (all-cis)-5,8,11,14,17-Eicosapentaenoic acid, EICOSAPENTAENOIC ACID (EPA) (C20:5 N3), L001256, Q409990, SR-01000946647, FA(20:5(5Z,8Z,11Z,14Z,17Z)), SR-01000946647-1, z,z,z,z,z-eicosa-5,8,11,14,17-pentaenoic acid, (Z,Z,Z,Z,Z)-5,8,11,14,17-eicosapentaenoic acid, BRD-K47192521-001-02-1, BRD-K47192521-001-05-4, cis-5,8,11,14,17-Eicosapentaenoic acid, >=99%, 7F8BF016-B146-4F72-A52E-B9298BA3A9AB, C20H30O2 (cis-5,8,11,14,17-eicosapentaenoic acid), Eicosapentaenoic acid, 5,8,11,14,17-(Z,Z,Z,Z,Z)-, 5,8,11,14,17-Eicosapentaenoic acid, (all-Z)- (8CI), cis-5,8,11,14,17-Eicosapentaenoic acid, >=85%, liquid, cis-5,8,11,14,17-Eicosapentaenoic acid, analytical standard, Eicosa-5Z,8Z,11Z,14Z,17Z-pentaenoic Acid (20:5, n-3), (5Z,8Z,11 Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acid, cis, cis, cis, cis, cis-eicosa-5,8,11,14,17-pentaenoic acid, 5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)- (9CI), (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acid, (all-Z)-5,8,11,14,17-Eicosapentaenoic acid, EPA, Timnodonic acid, 25377-48-4, cis-5,8,11,14,17-Eicosapentaenoic acid, 500 mug/mL in ethanol, certified reference material |
|---|---|
| Topological Polar Surface Area | 37.3 |
| Hydrogen Bond Donor Count | 1.0 |
| Heavy Atom Count | 22.0 |
| Description | Icosapent, also known as icosapentaenoate or (5z,8z,11z,14z,17z)-eicosapentaenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, icosapent is considered to be a fatty acid lipid molecule. Icosapent is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Icosapent can be found in a number of food items such as barley, sacred lotus, white lupine, and rape, which makes icosapent a potential biomarker for the consumption of these food products. Icosapent can be found primarily in blood, feces, sweat, and urine, as well as throughout most human tissues. In humans, icosapent is involved in the alpha linolenic acid and linoleic acid metabolism. Moreover, icosapent is found to be associated with essential hypertension and hypertension. Ethyl eicosapentaenoic acid (E-EPA, icosapent ethyl) is a derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA) that is used in combination with changes in diet to lower triglyceride levels in adults with severe (≥ 500 mg/dL) hypertriglyceridemia. This was the second class of fish oil-based drug to be approved for use as a drug and was approved by the FDA in 2012. These fish oil drugs are similar to fish oil dietary supplements but the ingredients are better controlled and have been tested in clinical trials . The anti-inflammatory, antithrombotic and immunomodulatory actions of EPA is probably due to its role in eicosanoid physiology and biochemistry. Most eicosanoids are produced by the metabolism of omega-3 fatty acids, specifically, arachidonic acid. These eicosanoids, leukotriene B4 (LTB4) and thromboxane A2 (TXA2) stimulate leukocyte chemotaxis, platelet aggregation and vasoconstriction. They are thrombogenic and artherogenic. On the other hand, EPA is metabolized to leukotriene B5 (LTB5) and thromboxane A3 (TXA3), which are eicosanoids that promote vasodilation, inhibit platelet aggregation and leukocyte chemotaxis and are anti-artherogenic and anti-thrombotic. The triglyceride-lowering effect of EPA results from inhibition of lipogenesis and stimulation of fatty acid oxidation. Fatty acid oxidation of EPA occurs mainly in the mitochondria. EPA is a substrate for Prostaglandin-endoperoxide synthase 1 and 2. It also appears to affect the function and bind to the Carbohydrate responsive element binding protein (ChREBP) and to a fatty acid receptor (G-coupled receptor) known as GP40 (DrugBank). |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 398.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | Q14032, O60488, O95573, P35354, P23219, O00154, P49753, Q8N9L9, O14734, O14842, P37231, Q8NER1, Q03181, O60427, P32418, Q86TX2, P79208, O62664, P13726, P00761, P11511, Q03164, P00352, Q9F4F7, Q96KQ7, P11473, P49798, Q9UBT6, O94782, O94925, Q07869, Q9NUW8, Q8TDS5, n.a., P19793, P10275 |
| Iupac Name | (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid |
| Prediction Hob | 1.0 |
| Class | Fatty Acyls |
| Target Id | NPT441, NPT1038, NPT94, NPT866, NPT106, NPT99, NPT4030, NPT546 |
| Xlogp | 5.6 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Fatty acids and conjugates |
| Molecular Formula | C20H30O2 |
| Prediction Swissadme | 0.0 |
| Inchi Key | JAZBEHYOTPTENJ-JLNKQSITSA-N |
| Fcsp3 | 0.45 |
| Logs | -2.688 |
| Rotatable Bond Count | 13.0 |
| State | Liquid |
| Logd | 1.953 |
| Synonyms | (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate, (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid, (all-Z)-5,8,11,14,17-Eicosapentaenoic acid, 5,8,11,14,17-EICOSAPENTAENOIC ACID, 5,8,11,14,17-Icosapentaenoic acid, all-cis-5,8,11,14,17-Eicosapentaenoic acid, all-cis-Icosa-5,8,11,14,17-pentaenoic acid, cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acid, cis-5,8,11,14,17-Eicosapentaenoic acid, cis-5,8,11,14,17-EPA, cis-Delta(5,8,11,14,17)-Eicosapentaenoic acid, EPA, Icosapent, Icosapentaenoic acid, Icosapento, Icosapentum, Timnodonic acid, (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoate, 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoate, (all-Z)-5,8,11,14,17-Eicosapentaenoate, 5,8,11,14,17-EICOSAPENTAENOate, 5,8,11,14,17-Icosapentaenoate, all-cis-5,8,11,14,17-Eicosapentaenoate, all-cis-Icosa-5,8,11,14,17-pentaenoate, cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoate, cis-5,8,11,14,17-Eicosapentaenoate, cis-delta(5,8,11,14,17)-Eicosapentaenoate, cis-Δ(5,8,11,14,17)-eicosapentaenoate, cis-Δ(5,8,11,14,17)-eicosapentaenoic acid, Icosapentaenoate, Timnodonate, 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate, (5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoate, Eicosapentaenoate, Omega-3-eicosapentaenoic acid, Acid, eicosapentanoic, Eicosapentanoic acid, Omega 3 eicosapentaenoic acid, all-cis-Icosapentaenoate, all-cis-Icosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-Eicosa-5,8,11,14,17-pentaenoic acid, (all-Z)-delta5,8,11,14,17-Eicosapentaenoic acid, (all-Z)-Δ5,8,11,14,17-eicosapentaenoic acid, (all-cis)-5,8,11,14,17-Eicosapentaenoic acid, FA(20:5(5Z,8Z,11Z,14Z,17Z)), FA(20:5n3), Eicosapentaenoic acid |
| Compound Name | Icosapent |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 302.225 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 302.225 |
| Hydrogen Bond Acceptor Count | 2.0 |
| Molecular Weight | 302.5 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 5.0 |
| Molecular Framework | Aliphatic acyclic compounds |
| Esol | -4.8199396 |
| 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- |
| Smiles | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O |
| Nring | 0.0 |
| Defined Bond Stereocenter Count | 5.0 |
| Taxonomy Direct Parent | Long-chain fatty acids |
- 1. Outgoing r'ship
FOUND_INto/from Alpinia Oxyphylla (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Arachis Hypogaea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 3. Outgoing r'ship
FOUND_INto/from Brassica Oleracea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Citrus Reticulata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Citrus Unshiu (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 6. Outgoing r'ship
FOUND_INto/from Glycine Max (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 7. Outgoing r'ship
FOUND_INto/from Helianthus Annuus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 8. Outgoing r'ship
FOUND_INto/from Phoenix Paludosa (Plant) Rel Props:Source_db:npass_chem_all - 9. Outgoing r'ship
FOUND_INto/from Plantago Major (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 10. Outgoing r'ship
FOUND_INto/from Portulaca Oleracea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 11. Outgoing r'ship
FOUND_INto/from Solanum Tuberosum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 12. Outgoing r'ship
FOUND_INto/from Sorghum Bicolor (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 13. Outgoing r'ship
FOUND_INto/from Syzygium Aromaticum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all