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(Z)-5,8,11,14,17-eicosapentaenoic acid
- Family: Plantae - Dictyotaceae
- Kingdom: Plantae
-
Class: Lipid
- Subclass: Fatty Acid
| Canonical 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 |
| Formula | C20H30O2 |
| HBA | 1 |
| HBD | 1 |
| MW | 302.46 |
| Rotatable Bonds | 13 |
| TPSA | 37.3 |
| LogP | 5.99 |
| Number Rings | 0 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.45 |
| Exact Mass | 302.22 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Zonaria tournefortii | Dictyotaceae | Plantae | 531995 |
Showing of synonyms
(Z)-5,8,11,14,17-eicosapentaenoic acid
Icosapent
EPA
Icosapento
Icosapentum
Miraxion
Eye Q
Eye-Q
Ropufa 70
Incromega e 7010sr
CCRIS 3279
AAN7QOV9EA
UNII-AAN7QOV9EA
EPA 45G
EPA [drug]
CHEBI:28364
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate
Icosapentum [INN-Latin]
Icosapento [INN-Spanish]
C20:5n-3,6,9,12,15
C20:5 (n-3)
EPA (drug)
Icosapentum (INN-Latin)
Icosapento (INN-Spanish)
RELIVEN
EPA-FFA
ICOSAPENT (EPA)
25377-48-4
Icosapentate
Eicosapentaenoic acid
Timnodonic acid
10417-94-4
Icosapentaenoic acid
Cis-5,8,11,14,17-Eicosapentaenoic acid
5,8,11,14,17-EICOSAPENTAENOIC ACID
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Eicosapentanoic acid
Eicosapentaenoate
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid
(all-Z)-5,8,11,14,17-Eicosapentaenoic acid
Icosapent [INN]
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid
5,8,11,14,17-Icosapentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid
MFCD00065716
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)
Icosapentaenoate
(all-Z)-delta5,8,11,14,17-Eicosapentaenoic acid
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)
(5Z,8Z,11Z,14Z,17Z)-icosapentaenoate
Timnodonate
3gwx
All-cis-icosapentaenoate
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
BP-40902
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)
Cis-5,8,11,14,17-Eicosapentaenoic acid, 500 mug/mL in ethanol, certified reference material
- El Hattab M, Bouzidi N, et al. (2009). Eicosapentaenoic acid: possible percursor of the phloroglucinol derivatives isolated from the brown alga Zonaria tournefortii (J.V. Lamouroux) Montagne. Biochemical Systematics and Ecology,2009,37(1),55-58. [View]
Pubchem:
446284
Cas:
25377-48-4
Gnps:
CCMSLIB00005738837
Zinc:
ZINC000004474603
Kegg Ligand:
C06428
Chebi:
28364
Nmrshiftdb2:
60018812
Metabolights:
MTBLC28364
Chembl:
CHEMBL460026
Comptox:
DTXSID9041023
Drugbank:
DB00159
Pdb Ligand:
EPA
Bindingdb:
50242349
CPRiL:
141
No scaffolds available.
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.58
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.51
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.99
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.45
- Plasma Protein Binding
- 76.8
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- -2.08
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.08
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.72
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.77
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Toxic
- NR-TR
- Safe
- T. Pyriformis
- -2.29
- Rat (Acute)
- 1.34
- Rat (Chronic Oral)
- 2.38
- Fathead Minnow
- 4.61
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Toxic
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 362.45
- Hydration Free Energy
- -5.36
- Log(D) at pH=7.4
- 2.6
- Log(P)
- 6.55
- Log S
- -4.02
- Log(Vapor Pressure)
- -6.35
- Melting Point
- -54.68
- pKa Acid
- 7.23
- pKa Basic
- 7.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.9852 |
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.9852 |
| 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | P9WNH5 | HSAD_MYCTU | Mycobacterium tuberculosis | 3 | 0.9500 |
| 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | P9WNH5 | HSAD_MYCTU | Mycobacterium tuberculosis | 3 | 0.9500 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7916 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7916 |
| Sodium/potassium-transporting ATPase subunit alpha | Q4H132 | Q4H132_SQUAC | Squalus acanthias | 2 | 0.7702 |
| Sodium/potassium-transporting ATPase subunit alpha | Q4H132 | Q4H132_SQUAC | Squalus acanthias | 2 | 0.7702 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 2 | 0.7600 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 2 | 0.7600 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7576 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7576 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7506 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7506 |
| 12-oxophytodienoate reductase 1 | Q9XG54 | OPR1_SOLLC | Solanum lycopersicum | 2 | 0.7463 |
| 12-oxophytodienoate reductase 1 | Q9XG54 | OPR1_SOLLC | Solanum lycopersicum | 2 | 0.7463 |
| Geranylgeranyl pyrophosphate synthase BTS1 | Q12051 | GGPPS_YEAST | Saccharomyces cerevisiae | 2 | 0.7446 |
| Geranylgeranyl pyrophosphate synthase BTS1 | Q12051 | GGPPS_YEAST | Saccharomyces cerevisiae | 2 | 0.7446 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7446 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7446 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7436 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7436 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7420 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7420 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7398 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7398 |
| Glutamate receptor ionotropic, kainate 1 | P22756 | GRIK1_RAT | Rattus norvegicus | 2 | 0.7382 |
| Glutamate receptor ionotropic, kainate 1 | P22756 | GRIK1_RAT | Rattus norvegicus | 2 | 0.7382 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7344 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7344 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 2 | 0.7282 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 2 | 0.7282 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7244 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7244 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7241 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7241 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7162 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7162 |
| Solanesyl diphosphate synthase 3, chloroplastic/mitochondrial | Q5HZ00 | SPS3_ARATH | Arabidopsis thaliana | 2 | 0.7110 |
| Solanesyl diphosphate synthase 3, chloroplastic/mitochondrial | Q5HZ00 | SPS3_ARATH | Arabidopsis thaliana | 2 | 0.7110 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7100 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7100 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7091 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7091 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7079 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7079 |
| Carnitine O-acetyltransferase | P47934 | CACP_MOUSE | Mus musculus | 2 | 0.7068 |
| Carnitine O-acetyltransferase | P47934 | CACP_MOUSE | Mus musculus | 2 | 0.7068 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7004 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7004 |