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The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at The data is made available under the Creative Commons License (CC BY 3.0, For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:oleoyl ethanolamide
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Accession:CHEBI:71466 term browser browse the term
Definition:An N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide.
Synonyms:exact_synonym: (9Z)-N-(2-hydroxyethyl)octadec-9-enamide
 related_synonym: Formula=C20H39NO2;   InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-;   InChIKey=BOWVQLFMWHZBEF-KTKRTIGZSA-N;   N-(2-Hydroxyethyl)-9-octadecenamide;   N-(2-Hydroxyethyl)oleamide;   N-(9Z-octadecenoyl)-ethanolamine;   N-(cis-9-octadecenoyl) ethanolamine;   N-(hydroxyethyl)oleamide;   N-Oleoylethanolamine;   N-oleoyl ethanolamine;   OEA;   Oleamide MEA;   Oleoyl monoethanolamide;   SMILES=CCCCCCCC\\C=C/CCCCCCCC(=O)NCCO;   oleoyl 1-ethanolamide;   oleoylethanolamide
 alt_id: CHEBI:77362
 xref: CAS:111-58-0;   DrugBank:DB16495;   FooDB:FDB022839;   HMDB:HMDB0002088;   LINCS:LSM-2694;   LIPID_MAPS_instance:LMFA08040015
 xref_mesh: MESH:C033595
 xref: MetaCyc:CPD-20398;   PMID:19521349;   PMID:20152858;   PMID:20534733;   PMID:20590573;   PMID:21250847;   PMID:21265075;   PMID:21375532;   PMID:21557271;   PMID:21562563;   PMID:21749725;   PMID:21801852;   PMID:21935601;   PMID:22046372;   PMID:22112961;   PMID:22154756;   PMID:22613942;   PMID:22701012;   PMID:22763622;   PMID:22825852;   PMID:22850591;   PMID:23201387;   Reaxys:2214880;   Wikipedia:Oleoylethanolamide

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oleoyl ethanolamide term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A increases export ISO ABCB1 protein results in increased export of N-oleoylethanolamine CTD PMID:30102254 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709
JBrowse link
G Ppara peroxisome proliferator activated receptor alpha increases response to substance
multiple interactions
ISO PPARA results in increased susceptibility to N-oleoylethanolamine
N-oleoylethanolamine binds to and results in increased activity of PPARA protein
CTD PMID:17906680 NCBI chr 7:116,832,405...116,900,878
Ensembl chr 7:116,832,756...116,895,346
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression ISO N-oleoylethanolamine results in decreased expression of PTGS2 protein CTD PMID:17906680 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19904
    role 19880
      chemical role 19500
        antioxidant 16060
          oleic acid 431
            oleoyl ethanolamide 3
              N-oleoylethanolamine phosphate(2-) 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19904
    subatomic particle 19902
      composite particle 19902
        hadron 19902
          baryon 19902
            nucleon 19902
              atomic nucleus 19902
                atom 19902
                  main group element atom 19852
                    p-block element atom 19852
                      carbon group element atom 19797
                        carbon atom 19792
                          organic molecular entity 19792
                            organic group 18983
                              organic divalent group 18958
                                organodiyl group 18958
                                  carbonyl group 18911
                                    carbonyl compound 18911
                                      carboxylic acid 18634
                                        carboacyl group 17707
                                          univalent carboacyl group 17707
                                            carbamoyl group 17552
                                              carboxamide 17552
                                                monocarboxylic acid amide 15691
                                                  fatty amide 829
                                                    N-(fatty acyl)-ethanolamine 52
                                                      N-(monounsaturated fatty acyl)ethanolamine 3
                                                        N-acylethanolamine 18:1 3
                                                          oleoyl ethanolamide 3
                                                            N-oleoylethanolamine phosphate(2-) 0
paths to the root