all-cis-5,8,11,14,17-icosapentaenoic acid
CHEBI:28364 EXACT SEEDED enzyme inhibitor
An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.
Structure
| Standard InChIKey | JAZBEHYOTPTENJ-JLNKQSITSA-N |
|---|---|
| SMILES | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:446284 |
Filing pathway
Fatty acids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is other, from MIBiG.
Producer organisms 4
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Shewanella sp. BR-2 NCBITaxon:563072 |
SOURCE_ASSERTION | mibig:BGC0000861 | PMID:19809243 |
| Shewanella pneumatophori NCBITaxon:314092 |
SOURCE_ASSERTION | mibig:BGC0000862 | PMID:9274025 |
| Pseudoalteromonas sp. DS-12 NCBITaxon:375285 |
SOURCE_ASSERTION | mibig:BGC0000863 | PMID:17122401 |
| Photobacterium profundum SS9 NCBITaxon:298386 |
SOURCE_ASSERTION | mibig:BGC0000865 | PMID:12055309 |
Occurrences 25
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Mus musculus NCBITaxon:10090 |
CHEBI | MTBLS143 |
| Eurhynchium striatum NCBITaxon:113274 |
LOTUS | DOI:10.1016/0031-9422(91)85024-T |
| Alpinia oxyphylla NCBITaxon:125261 |
LOTUS | DOI:10.1016/J.JPBA.2014.10.014 |
| Sphagnum palustre NCBITaxon:13805 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Dicranum japonicum NCBITaxon:1385677 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Ulota crispa NCBITaxon:140636 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Nannochloropsis oceanica NCBITaxon:145522 |
LOTUS | DOI:10.1016/J.BIORTECH.2014.12.012 |
| Scopelophila cataractae NCBITaxon:146586 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Perilla frutescens NCBITaxon:151328 |
LOTUS | DOI:10.3390/MOLECULES25092099 |
| Ptilota filicina NCBITaxon:153248 |
LOTUS | DOI:10.1021/BI00255A002 |
| Thuidium pristocalyx NCBITaxon:171374 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Thuidium glaucinum NCBITaxon:173666 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Hedlundia hybrida NCBITaxon:1775740 |
LOTUS | DOI:10.1021/JF071791S |
| Brachythecium buchananii NCBITaxon:184619 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Oncophorus crispifolius NCBITaxon:1852632 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Pogonatum inflexum NCBITaxon:185755 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Campylopus richardii NCBITaxon:193026 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Dolichomitra cymbifolia NCBITaxon:195670 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Rhizomnium tuomikoskii NCBITaxon:2006508 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Fissidens nobilis NCBITaxon:2008595 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Sarcophyton trocheliophorum NCBITaxon:205097 |
LOTUS | DOI:10.1016/S0040-4020(01)00853-5 |
| Tornabea scutellifera NCBITaxon:205647 |
LOTUS | DOI:10.1002/CHIN.199517179 |
| Wijkia concavifolia NCBITaxon:213177 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
| Shewanella NCBITaxon:22 |
LOTUS | DOI:10.4014/JMB.0902.090 |
| Grimmia pilifera NCBITaxon:254107 |
LOTUS | DOI:10.1016/0031-9422(91)83188-Q |
Biosynthetic gene clusters 4
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000861 | Shewanella sp. BR-2 NCBITaxon:563072 |
CLUSTER_UNSTATED | genbank:EU719604.1 |
| mibig:BGC0000862 | Shewanella pneumatophori NCBITaxon:314092 |
CLUSTER_UNSTATED | genbank:U73935.1 |
| mibig:BGC0000863 | Pseudoalteromonas sp. DS-12 NCBITaxon:375285 |
CLUSTER_UNSTATED | genbank:DQ469875.1 |
| mibig:BGC0000865 | Photobacterium profundum SS9 NCBITaxon:298386 |
CLUSTER_UNSTATED | genbank:AF409100.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Causal graph — bioactivity 2 nodes, 1 edges
all-cis-5,8,11,14,17-icosapentaenoic acid binds the human PPAR-delta ligand-binding domain captured in PDB 3GWX.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| all-cis-5,8,11,14,17-icosapentaenoic acid | binds | human peroxisome proliferator-activated receptor delta | DOI:10.1016/S1097-2765(00)80467-0 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| Confirmatory qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) | 8.1905 uM | pubchem.aid:1964105 |
| Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB | IC50 4 uM | PMID:10198642 |
| HepG2 viability counterscreen (readout 1: protease activity) against the NCATS DSHEA and TCM libraries | 12.5893 uM | PMID:37200814 |
| Inhibitors of Regulator of G Protein Signaling (RGS) 4: qHTS | 8.4368 uM | pubchem.aid:504845 |
| Inhibitors of USP1/UAF1: Pilot qHTS | 79.4328 uM | pubchem.aid:504865 |
| Inhibitors of the vitamin D receptor (VDR): qHTS | 39.8107 uM | pubchem.aid:504847 |
| Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4) | 11.2202 uM | pubchem.aid:1845192 |
| Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4) | 11.2202 uM | pubchem.aid:1845192 |
| Primary qHTS for agonist of constitutive androstane receptor (CAR) against the NCATS DSHEA and TCM libraries | 14.1254 uM | pubchem.aid:1794839 |
| Primary qHTS for antagonist of constitutive androstane receptor (CAR) against the NCATS DSHEA and TCM libraries | 3.1623 uM | PMID:37200814 |
| Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) | 7.8513 uM | pubchem.aid:1964107 |
| Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Endogenous NS2/3 peptide Counterscreen | 37.5444 uM | pubchem.aid:1964103 |
| Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Full length NSP2 enzyme counterscreen (CHIKV-NSP2) | 6.6764 uM | pubchem.aid:1964101 |
| Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Papain Counterscreen | 33.4615 uM | pubchem.aid:1964104 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 100 uM | pubchem.aid:1645883 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 100 uM | pubchem.aid:1645883 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 79.4328 uM | pubchem.aid:1645887 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 79.4328 uM | pubchem.aid:1645887 |
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 0.631 uM | pubchem.aid:1645882 |
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 0.631 uM | pubchem.aid:1645882 |
| qHTS Assay for Inhibitors of Aldehyde Dehydrogenase 1 (ALDH1A1) | 39.8107 uM | pubchem.aid:1030 |
| qHTS Assay for Inhibitors of Bacillus subtilis Sfp phosphopantetheinyl transferase (PPTase) | 89.1251 uM | pubchem.aid:1490 |
| qHTS Assay for Inhibitors of Bacillus subtilis Sfp phosphopantetheinyl transferase (PPTase) | 70.7946 uM | pubchem.aid:1490 |
| qHTS Assay for Inhibitors of Histone Lysine Methyltransferase G9a | 5.0119 uM | pubchem.aid:504332 |
| qHTS Fluorescence Polarization Assay for Inhibitors of MLL CXXC domain - DNA interaction | 50.1187 uM | pubchem.aid:2662 |
Open questions 2
name-disagreement — ChEBI calls this structure 'all-cis-5,8,11,14,17-icosapentaenoic acid' and MIBiG calls it 'eicosapentaenoic acid', 'eicoseicosapentaenoic acid'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000861, BGC0000862, BGC0000863, BGC0000865. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000861 | MIBIG | 5 |
| BGC0000862 | MIBIG | 3 |
| BGC0000863 | MIBIG | 3 |
| BGC0000865 | MIBIG | 3 |
| CHEBI:28364 | CHEBI | 3-star |
This page is generated from data/natural_products/fatty_acids/all-cis-5-8-11-14-17-icosapentaenoic-acid.yaml, which is generated from the committed inventories. Neither is edited by hand.