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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/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:palmitoleic acid
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Accession:CHEBI:28716 term browser browse the term
Definition:A hexadec-9-enoic acid in which the double bond at position C-9 has cis configuration.
Synonyms:exact_synonym: (9Z)-hexadec-9-enoic acid
 related_synonym: (9Z)-Hexadecenoic acid;   (Z)-9-hexadecenoic acid;   (Z)-hexadec-9-enoic acid;   16:1Delta9;   9-cis-hexadecenoic acid;   Formula=C16H30O2;   InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-;   InChIKey=SECPZKHBENQXJG-FPLPWBNLSA-N;   Oleopalmitic acid;   SMILES=C(CCCCCCC/C=C\\CCCCCC)(=O)O;   Zoomeric acid;   cis-9-Palmitoleic acid;   cis-Palmitoleic acid;   cis-delta-9-Hexadecenoic acid;   palmitolinoleic acid;   zoomaric acid
 alt_id: CHEBI:25836;   CHEBI:44696;   CHEBI:7897
 xref: Beilstein:1725389;   CAS:373-49-9;   DrugBank:DB04257;   HMDB:HMDB0003229;   KEGG:C08362;   KNApSAcK:C00001234;   KNApSAcK:C00029354;   LIPID_MAPS_instance:LMFA01030056
 xref_mesh: MESH:C008757
 xref: PDBeChem:PAM;   PMID:19761868;   PMID:24362891;   Reaxys:1725389
 cyclic_relationship: is_conjugate_acid_of CHEBI:32372


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palmitoleic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abca1 ATP binding cassette subfamily A member 1 increases degradation
increases phosphorylation
multiple interactions		 ISO palmitoleic acid results in increased degradation of ABCA1 protein
palmitoleic acid results in increased phosphorylation of ABCA1 protein
palmitoleic acid inhibits the reaction [APOA1 protein affects the reaction [ABCA1 protein results in increased transport of Cholesterol]]; palmitoleic acid inhibits the reaction [APOA1 protein affects the reaction [ABCA1 protein results in increased transport of Phospholipids]]		 CTD PMID:16118212 NCBI chr 5:67,678,267...67,801,162
Ensembl chr 5:67,681,297...67,801,170 		JBrowse link
G Apoa1 apolipoprotein A1 multiple interactions ISO palmitoleic acid inhibits the reaction [APOA1 protein affects the reaction [ABCA1 protein results in increased transport of Cholesterol]]; palmitoleic acid inhibits the reaction [APOA1 protein affects the reaction [ABCA1 protein results in increased transport of Phospholipids]] CTD PMID:16118212 NCBI chr 8:46,527,251...46,529,035
Ensembl chr 8:46,527,144...46,529,035 		JBrowse link
G Il6 interleukin 6 increases expression ISO palmitoleic acid results in increased expression of IL6 mRNA CTD PMID:30524225 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Ins2 insulin 2 multiple interactions ISO [1-Methyl-3-isobutylxanthine co-treated with Dexamethasone co-treated with INS protein] results in increased abundance of palmitoleic acid analog CTD PMID:26820058 NCBI chr 1:197,843,277...197,992,522
Ensembl chr 1:197,843,281...197,864,775 		JBrowse link
G Pck1 phosphoenolpyruvate carboxykinase 1 multiple interactions ISO [Glucose deficiency co-treated with palmitoleic acid] results in increased expression of PCK1 mRNA CTD PMID:8536680 NCBI chr 3:161,930,256...161,936,205
Ensembl chr 3:161,930,256...161,936,191 		JBrowse link
G Pon1 paraoxonase 1 multiple interactions
decreases activity		 ISO palmitoleic acid inhibits the reaction [[Ascorbic Acid co-treated with Copper Sulfate] results in decreased activity of PON1 protein]; palmitoleic acid inhibits the reaction [PON1 protein results in increased hydrolysis of Paraoxon]
palmitoleic acid results in decreased activity of PON1 protein		 CTD PMID:12871208 PMID:15375178 NCBI chr 4:33,294,737...33,325,759
Ensembl chr 4:33,294,722...33,321,360 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19800
    role 19751
      biological role 19751
        biochemical role 19368
          metabolite 19344
            eukaryotic metabolite 19033
              algal metabolite 13975
                palmitoleic acid 6
                  1,2,3-tripalmitoleoylglycerol 0
                  1,2-di-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphate 0
                  1,2-di-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphoethanolamine 0
                  1,2-di-[(9Z)-hexadecenoyl]glycerol 0
                  1,2-di-palmitoleoyl-2-sn-glycerol 0
                  1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine 0
                  1,2-dipalmitoyl-3-palmitoleoyl-sn-glycerol 0
                  1,3-dipalmitoleoylglycerol 0
                  1-(1Z-hexadecenyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine 0
                  1-(9Z)-octadecenoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphate 0
                  1-[(9Z)-hexadecenoyl]-2-[(11Z)-octadecenoyl]-sn-glycero-3-phosphocholine 0
                  1-[(9Z)-hexadecenoyl]-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine 0
                  1-[(9Z)-hexadecenoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine 0
                  1-[(9Z)-hexadecenoyl]-2-[(9Z)-tetradecenoyl]-sn-glycero-3-phosphocholine 0
                  1-[(9Z)-hexadecenoyl]-2-acetyl-sn-glycero-3-phosphocholine 0
                  1-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                  1-[(9Z)-hexadecenoyl]glycerol 0
                  1-[(9Z)-hexadecenyl]-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                  1-[(9Z)-octadecenoyl]-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                  1-acyl-2-palmitoleoyl-sn-glycero-3-phosphocholine + 0
                  1-acyl-2-palmitoleoylglycerolipid 0
                  1-myristoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine 0
                  1-myristoyl-2-palmitoleoyl-sn-glycerol 0
                  1-octadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphate 0
                  1-octadecanoyl-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                  1-oleoyl-2-palmitoleoyl-sn-glycero-3-phospho-L-serine 0
                  1-oleoyl-2-palmitoleoyl-sn-glycero-3-phosphoethanolamine 0
                  1-palmitoleoyl-2-linoleoyl-sn-glycero-3-phosphocholine 0
                  1-palmitoleoyl-2-linoleoyl-sn-glycerol 0
                  1-palmitoleoyl-2-stearoyl-sn-glycero-3-phosphocholine 0
                  1-palmitoleoyl-2-stearoyl-sn-glycerol 0
                  1-palmitoleoyl-sn-glycerol 3-phosphate 0
                  1-palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine 0
                  1-palmitoyl-2-palmitoleoyl-sn-glycerol 0
                  1-tetradecyl-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                  12-[(9Z)-hexadecenoyloxy]octadecanoic acid 0
                  13-[(9Z)-hexadecenoyloxy]octadecanoic acid 0
                  2,3-dipalmitoleoyl-sn-glycerol 0
                  2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                  2-[(9Z)-hexadecenoyl]glycerol 0
                  2-hydroxypalmitoleic acid 0
                  5-[(9Z)-hexadecenoyloxy]octadecanoic acid 0
                  9-[(9Z)-hexadecenoyloxy]octadecanoic acid 0
                  N-[(9Z)-hexadecenoyl]glycine 0
                  [(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine + 0
                  cholesteryl palmitoleate 0
                  episteryl palmitoleate 0
                  ethyl palmitoleate 0
                  lauryl palmitoleate 0
                  methyl palmitoleate 0
                  palmitoleamide 0
                  palmitoleoyl ethanolamide 0
                  palmitoleoyl-CoA 0
                  palmitoleoyl-containing glycerolipid 0
                  palmityl palmitoleate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19800
    subatomic particle 19799
      composite particle 19799
        hadron 19799
          baryon 19799
            nucleon 19799
              atomic nucleus 19799
                atom 19799
                  main group element atom 19698
                    p-block element atom 19698
                      carbon group element atom 19619
                        carbon atom 19609
                          organic molecular entity 19609
                            organic group 18718
                              organic divalent group 18702
                                organodiyl group 18702
                                  carbonyl group 18651
                                    carbonyl compound 18651
                                      carboxylic acid 18346
                                        monocarboxylic acid 17622
                                          fatty acid 16011
                                            unsaturated fatty acid 957
                                              monounsaturated fatty acid 453
                                                hexadecenoic acid 6
                                                  hexadec-9-enoic acid 6
                                                    palmitoleic acid 6
                                                      1,2,3-tripalmitoleoylglycerol 0
                                                      1,2-di-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphate 0
                                                      1,2-di-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphoethanolamine 0
                                                      1,2-di-[(9Z)-hexadecenoyl]glycerol 0
                                                      1,2-di-palmitoleoyl-2-sn-glycerol 0
                                                      1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine 0
                                                      1,2-dipalmitoyl-3-palmitoleoyl-sn-glycerol 0
                                                      1,3-dipalmitoleoylglycerol 0
                                                      1-(1Z-hexadecenyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine 0
                                                      1-(9Z)-octadecenoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphate 0
                                                      1-[(9Z)-hexadecenoyl]-2-[(11Z)-octadecenoyl]-sn-glycero-3-phosphocholine 0
                                                      1-[(9Z)-hexadecenoyl]-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine 0
                                                      1-[(9Z)-hexadecenoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine 0
                                                      1-[(9Z)-hexadecenoyl]-2-[(9Z)-tetradecenoyl]-sn-glycero-3-phosphocholine 0
                                                      1-[(9Z)-hexadecenoyl]-2-acetyl-sn-glycero-3-phosphocholine 0
                                                      1-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                                                      1-[(9Z)-hexadecenoyl]glycerol 0
                                                      1-[(9Z)-hexadecenyl]-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                                                      1-[(9Z)-octadecenoyl]-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                                                      1-acyl-2-palmitoleoyl-sn-glycero-3-phosphocholine + 0
                                                      1-acyl-2-palmitoleoylglycerolipid 0
                                                      1-myristoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine 0
                                                      1-myristoyl-2-palmitoleoyl-sn-glycerol 0
                                                      1-octadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphate 0
                                                      1-octadecanoyl-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                                                      1-oleoyl-2-palmitoleoyl-sn-glycero-3-phospho-L-serine 0
                                                      1-oleoyl-2-palmitoleoyl-sn-glycero-3-phosphoethanolamine 0
                                                      1-palmitoleoyl-2-linoleoyl-sn-glycero-3-phosphocholine 0
                                                      1-palmitoleoyl-2-linoleoyl-sn-glycerol 0
                                                      1-palmitoleoyl-2-stearoyl-sn-glycero-3-phosphocholine 0
                                                      1-palmitoleoyl-2-stearoyl-sn-glycerol 0
                                                      1-palmitoleoyl-sn-glycerol 3-phosphate 0
                                                      1-palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine 0
                                                      1-palmitoyl-2-palmitoleoyl-sn-glycerol 0
                                                      1-tetradecyl-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                                                      12-[(9Z)-hexadecenoyloxy]octadecanoic acid 0
                                                      13-[(9Z)-hexadecenoyloxy]octadecanoic acid 0
                                                      2,3-dipalmitoleoyl-sn-glycerol 0
                                                      2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine 0
                                                      2-[(9Z)-hexadecenoyl]glycerol 0
                                                      2-hydroxypalmitoleic acid 0
                                                      5-[(9Z)-hexadecenoyloxy]octadecanoic acid 0
                                                      9-[(9Z)-hexadecenoyloxy]octadecanoic acid 0
                                                      N-[(9Z)-hexadecenoyl]glycine 0
                                                      [(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine + 0
                                                      cholesteryl palmitoleate 0
                                                      episteryl palmitoleate 0
                                                      ethyl palmitoleate 0
                                                      lauryl palmitoleate 0
                                                      methyl palmitoleate 0
                                                      palmitoleamide 0
                                                      palmitoleoyl ethanolamide 0
                                                      palmitoleoyl-CoA 0
                                                      palmitoleoyl-containing glycerolipid 0
                                                      palmityl palmitoleate 0
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