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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:icosa-5,8,11,13-tetraenoic acid
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Accession:CHEBI:36035 term browser browse the term
Definition:Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 13.
Synonyms:related_synonym: 20:4, n-7,9,12,15;   5,8,11,13-eicosatetraenoic acid;   5,8,11,13-eicosatetraenoic acids;   5,8,11,13-icosatetraenoic acid;   5,8,11,13-icosatetraenoic acids;   C20:4, n-7,9,12,15;   Formula=C20H32O2;   InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h7-10,12-13,15-16H,2-6,11,14,17-19H2,1H3,(H,21,22);   InChIKey=IJAXPCZCTKDWBJ-UHFFFAOYSA-N;   SMILES=[H]C(CCCC(O)=O)=CCC([H])=CCC([H])=CC([H])=CCCCCCC;   eicosa-5,8,11,13-tetraenoic acid;   eicosa-5,8,11,13-tetraenoic acids;   icosa-5,8,11,13-tetraenoic acids


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(5Z,8Z,11Z,13E)-15-HETE term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Alox15 arachidonate 15-lipoxygenase multiple interactions
increases abundance
increases chemical synthesis
ISO
EXP
[[Oxygen deficiency results in increased activity of ALOX15 protein] which results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid] which results in decreased expression of KCNA5 mRNA; [[Oxygen deficiency results in increased activity of ALOX15 protein] which results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid] which results in decreased expression of KCNA5 protein; [Oxygen deficiency results in increased activity of ALOX15 protein] which results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid; cinnamyl-3,4-dihydroxycyanocinnamate inhibits the reaction [[[Oxygen deficiency results in increased activity of ALOX15 protein] which results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid] which results in decreased expression of KCNA5 mRNA]; Masoprocol inhibits the reaction [[[Oxygen deficiency results in increased activity of ALOX15 protein] which results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid] which results in decreased expression of KCNA5 mRNA]
ALOX15 protein results in increased abundance of 15-hydroxy-5,8,11,13-eicosatetraenoic acid
ALOX15 protein results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid
[ALOX15 protein affects the metabolism of Arachidonic Acid] which results in increased abundance of 15-hydroxy-5,8,11,13-eicosatetraenoic acid
CTD PMID:18984061 PMID:21193584 PMID:23872364 NCBI chr11:70,344,147...70,390,538
Ensembl chr11:70,344,152...70,352,031
JBrowse link
G Alox5 arachidonate 5-lipoxygenase multiple interactions ISO [benoxaprofen results in decreased activity of ALOX5 protein] which results in increased abundance of 15-hydroxy-5,8,11,13-eicosatetraenoic acid; [Masoprocol results in decreased activity of ALOX5 protein] which results in increased abundance of 15-hydroxy-5,8,11,13-eicosatetraenoic acid; [RS 43179 results in decreased activity of ALOX5 protein] which results in increased abundance of 15-hydroxy-5,8,11,13-eicosatetraenoic acid; [tenidap results in decreased activity of ALOX5 protein] which results in increased abundance of 15-hydroxy-5,8,11,13-eicosatetraenoic acid CTD PMID:2849922 NCBI chr 6:116,410,071...116,461,178
Ensembl chr 6:116,410,077...116,461,178
JBrowse link
G App amyloid beta (A4) precursor protein increases secretion
multiple interactions
ISO APP protein modified form results in increased secretion of 15-hydroxy-5,8,11,13-eicosatetraenoic acid
CNB 001 inhibits the reaction [APP protein modified form results in increased secretion of 15-hydroxy-5,8,11,13-eicosatetraenoic acid]; Dronabinol inhibits the reaction [APP protein modified form results in increased secretion of 15-hydroxy-5,8,11,13-eicosatetraenoic acid]; L 685458 inhibits the reaction [APP protein modified form results in increased secretion of 15-hydroxy-5,8,11,13-eicosatetraenoic acid]
CTD PMID:28721267 NCBI chr16:84,952,666...85,175,255
Ensembl chr16:84,949,685...85,173,766
JBrowse link
G Egf epidermal growth factor multiple interactions
increases chemical synthesis
ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid promotes the reaction [EGF protein affects the localization of PRKCA protein]
EGF protein results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid
CTD PMID:15613483 NCBI chr 3:129,677,574...129,755,322
Ensembl chr 3:129,677,565...129,755,316
JBrowse link
G Ephx2 epoxide hydrolase 2, cytoplasmic increases activity ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased activity of EPHX2 protein CTD PMID:25600587 NCBI chr14:66,084,372...66,124,522
Ensembl chr14:66,084,374...66,124,500
JBrowse link
G Hgf hepatocyte growth factor multiple interactions ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid promotes the reaction [HGF protein affects the localization of PRKCA protein] CTD PMID:15613483 NCBI chr 5:16,553,495...16,619,439
Ensembl chr 5:16,553,495...16,620,152
JBrowse link
G Il1b interleukin 1 beta multiple interactions
increases secretion
ISO IL1B protein affects the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]; IL1B protein affects the reaction [TNF protein affects the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]]; TNF protein affects the reaction [IL1B protein affects the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]]
15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of IL1B protein
CTD PMID:23355332 NCBI chr 2:129,364,569...129,371,164
Ensembl chr 2:129,364,570...129,371,139
JBrowse link
G Kcna5 potassium voltage-gated channel, shaker-related subfamily, member 5 multiple interactions
affects activity
ISO [[Oxygen deficiency results in increased activity of ALOX15 protein] which results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid] which results in decreased expression of KCNA5 mRNA; [[Oxygen deficiency results in increased activity of ALOX15 protein] which results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid] which results in decreased expression of KCNA5 protein; cinnamyl-3,4-dihydroxycyanocinnamate inhibits the reaction [[[Oxygen deficiency results in increased activity of ALOX15 protein] which results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid] which results in decreased expression of KCNA5 mRNA]; Masoprocol inhibits the reaction [[[Oxygen deficiency results in increased activity of ALOX15 protein] which results in increased chemical synthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid] which results in decreased expression of KCNA5 mRNA]
15-hydroxy-5,8,11,13-eicosatetraenoic acid affects the activity of KCNA5 protein
CTD PMID:18984061 NCBI chr 6:126,532,551...126,535,555
Ensembl chr 6:126,532,551...126,535,412
JBrowse link
G Kcnb1 potassium voltage gated channel, Shab-related subfamily, member 1 affects activity ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid affects the activity of KCNB1 protein CTD PMID:18984061 NCBI chr 2:167,095,969...167,190,072
Ensembl chr 2:167,095,969...167,190,155
JBrowse link
G Kcnc4 potassium voltage gated channel, Shaw-related subfamily, member 4 affects activity ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid affects the activity of KCNC4 protein CTD PMID:18984061 NCBI chr 3:107,438,298...107,460,287
Ensembl chr 3:107,438,303...107,459,552
JBrowse link
G Krt1 keratin 1 multiple interactions EXP 15-hydroxy-5,8,11,13-eicosatetraenoic acid inhibits the reaction [Calcium results in increased expression of KRT1 mRNA] CTD PMID:12069687 NCBI chr15:101,845,426...101,850,786
Ensembl chr15:101,845,426...101,850,794
JBrowse link
G Lyz2 lysozyme 2 increases secretion
multiple interactions
ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein
[parthenolide co-treated with artemisinine co-treated with Quercetin] inhibits the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]; artemisinine inhibits the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]; IL1B protein affects the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]; IL1B protein affects the reaction [TNF protein affects the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]]; parthenolide inhibits the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]; Quercetin inhibits the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]; SB 203580 inhibits the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]; TNF protein affects the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]; TNF protein affects the reaction [IL1B protein affects the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]]
CTD PMID:23355332 NCBI chr10:117,277,541...117,282,272
Ensembl chr10:117,277,331...117,282,321
JBrowse link
G Mapk1 mitogen-activated protein kinase 1 increases phosphorylation ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased phosphorylation of MAPK1 protein CTD PMID:25600587 NCBI chr16:16,983,382...17,047,453
Ensembl chr16:16,983,382...17,047,453
JBrowse link
G Mapk3 mitogen-activated protein kinase 3 increases phosphorylation ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased phosphorylation of MAPK3 protein CTD PMID:25600587 NCBI chr 7:126,759,626...126,765,816
Ensembl chr 7:126,759,601...126,765,819
JBrowse link
G Nfkb1 nuclear factor of kappa light polypeptide gene enhancer in B cells 1, p105 increases activity
affects localization
multiple interactions
ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased activity of NFKB1 protein
15-hydroxy-5,8,11,13-eicosatetraenoic acid affects the localization of NFKB1 protein
artemisinine inhibits the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid affects the localization of NFKB1 protein]
CTD PMID:23355332 PMID:25600587 NCBI chr 3:135,584,655...135,691,969
Ensembl chr 3:135,584,655...135,691,547
JBrowse link
G Nfkbia nuclear factor of kappa light polypeptide gene enhancer in B cells inhibitor, alpha multiple interactions EXP
ISO
15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased phosphorylation of and results in increased degradation of NFKBIA protein; calphostin C inhibits the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased phosphorylation of and results in increased degradation of NFKBIA protein]
15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased phosphorylation of and results in increased degradation of NFKBIA protein; Quercetin inhibits the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased phosphorylation of and results in increased degradation of NFKBIA protein]
CTD PMID:15451026 PMID:23355332 NCBI chr12:55,489,409...55,492,647
Ensembl chr12:55,489,410...55,492,647
JBrowse link
G Nppa natriuretic peptide type A increases expression ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased expression of NPPA mRNA CTD PMID:25600587 NCBI chr 4:148,000,722...148,002,074
Ensembl chr 4:148,000,722...148,002,079
JBrowse link
G Nppb natriuretic peptide type B increases expression ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased expression of NPPB mRNA CTD PMID:25600587 NCBI chr 4:147,985,786...147,987,205
Ensembl chr 4:147,985,788...147,987,205
JBrowse link
G Ppard peroxisome proliferator activator receptor delta multiple interactions EXP 15-hydroxy-5,8,11,13-eicosatetraenoic acid binds to and results in increased activity of PPARD protein CTD PMID:12069687 NCBI chr17:28,232,754...28,301,469
Ensembl chr17:28,232,700...28,301,474
JBrowse link
G Prkca protein kinase C, alpha multiple interactions
increases activity
affects localization
ISO
EXP
15-hydroxy-5,8,11,13-eicosatetraenoic acid promotes the reaction [EGF protein affects the localization of PRKCA protein]; 15-hydroxy-5,8,11,13-eicosatetraenoic acid promotes the reaction [HGF protein affects the localization of PRKCA protein]
calphostin C inhibits the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased activity of PRKCA protein]
15-hydroxy-5,8,11,13-eicosatetraenoic acid affects the localization of PRKCA protein
CTD PMID:15451026 PMID:15613483 NCBI chr11:107,933,387...108,343,888
Ensembl chr11:107,933,387...108,343,928
JBrowse link
G Rela v-rel reticuloendotheliosis viral oncogene homolog A (avian) increases activity
affects localization
multiple interactions
ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased activity of RELA protein
15-hydroxy-5,8,11,13-eicosatetraenoic acid affects the localization of RELA protein
artemisinine inhibits the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid affects the localization of RELA protein]
CTD PMID:23355332 PMID:25600587 NCBI chr19:5,637,442...5,648,134
Ensembl chr19:5,637,483...5,648,130
JBrowse link
G Tnf tumor necrosis factor increases secretion
multiple interactions
ISO 15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of TNF protein
IL1B protein affects the reaction [TNF protein affects the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]]; TNF protein affects the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]; TNF protein affects the reaction [IL1B protein affects the reaction [15-hydroxy-5,8,11,13-eicosatetraenoic acid results in increased secretion of LYZ protein]]
CTD PMID:23355332 NCBI chr17:35,199,367...35,202,007
Ensembl chr17:35,199,381...35,202,007
JBrowse link
G Ugt1a1 UDP glucuronosyltransferase 1 family, polypeptide A1 increases glucuronidation ISO UGT1A1 protein results in increased glucuronidation of 15-hydroxy-5,8,11,13-eicosatetraenoic acid CTD PMID:15231852 NCBI chr 1:88,211,959...88,220,002
Ensembl chr 1:88,211,959...88,218,997
JBrowse link
G Ugt1a10 UDP glycosyltransferase 1 family, polypeptide A10 increases glucuronidation ISO UGT1A10 protein results in increased glucuronidation of 15-hydroxy-5,8,11,13-eicosatetraenoic acid CTD PMID:15231852 NCBI chr 1:88,055,411...88,220,002
Ensembl chr 1:88,055,388...88,219,004
JBrowse link
G Ugt1a2 UDP glucuronosyltransferase 1 family, polypeptide A2 increases glucuronidation ISO UGT1A3 protein results in increased glucuronidation of 15-hydroxy-5,8,11,13-eicosatetraenoic acid CTD PMID:15231852 NCBI chr 1:88,200,611...88,220,002
Ensembl chr 1:88,200,601...88,218,997
JBrowse link
G Ugt1a5 UDP glucuronosyltransferase 1 family, polypeptide A5 increases glucuronidation ISO UGT1A4 protein results in increased glucuronidation of 15-hydroxy-5,8,11,13-eicosatetraenoic acid CTD PMID:15231852 NCBI chr 1:88,166,012...88,220,002
Ensembl chr 1:88,166,012...88,218,997
JBrowse link
G Ugt1a9 UDP glucuronosyltransferase 1 family, polypeptide A9 increases glucuronidation ISO UGT1A9 protein results in increased glucuronidation of 15-hydroxy-5,8,11,13-eicosatetraenoic acid CTD PMID:15231852 NCBI chr 1:88,070,779...88,220,002
Ensembl chr 1:88,070,800...88,218,997
JBrowse link
G Ugt2b34 UDP glucuronosyltransferase 2 family, polypeptide B34 increases glucuronidation ISO UGT2B7 protein results in increased glucuronidation of 15-hydroxy-5,8,11,13-eicosatetraenoic acid CTD PMID:15231852 NCBI chr 5:86,889,770...86,906,937
Ensembl chr 5:86,889,767...86,906,937
JBrowse link
15-oxo-ETE term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Hmox1 heme oxygenase 1 increases expression ISO 15-keto-5,8,11,13-eicosatetraenoic acid results in increased expression of HMOX1 protein CTD PMID:25450232 NCBI chr 8:75,093,618...75,100,593
Ensembl chr 8:75,093,621...75,100,589
JBrowse link
G Ikbkb inhibitor of kappaB kinase beta multiple interactions
decreases activity
ISO [15-keto-5,8,11,13-eicosatetraenoic acid results in decreased activity of IKBKB protein] which results in decreased phosphorylation of NFKBIA protein CTD PMID:25450232 NCBI chr 8:22,659,205...22,706,589
Ensembl chr 8:22,659,212...22,706,589
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO 15-keto-5,8,11,13-eicosatetraenoic acid inhibits the reaction [Lipopolysaccharides results in increased expression of IL1B mRNA] CTD PMID:25450232 NCBI chr 2:129,364,569...129,371,164
Ensembl chr 2:129,364,570...129,371,139
JBrowse link
G Il6 interleukin 6 multiple interactions ISO 15-keto-5,8,11,13-eicosatetraenoic acid inhibits the reaction [Lipopolysaccharides results in increased expression of IL6 mRNA] CTD PMID:25450232 NCBI chr 5:30,013,114...30,019,975
Ensembl chr 5:30,013,114...30,019,981
JBrowse link
G Nfkbia nuclear factor of kappa light polypeptide gene enhancer in B cells inhibitor, alpha multiple interactions ISO [15-keto-5,8,11,13-eicosatetraenoic acid results in decreased activity of IKBKB protein] which results in decreased phosphorylation of NFKBIA protein CTD PMID:25450232 NCBI chr12:55,489,409...55,492,647
Ensembl chr12:55,489,410...55,492,647
JBrowse link
G Nqo1 NAD(P)H dehydrogenase, quinone 1 increases expression ISO 15-keto-5,8,11,13-eicosatetraenoic acid results in increased expression of NQO1 protein CTD PMID:25450232 NCBI chr 8:107,388,225...107,403,205
Ensembl chr 8:107,388,225...107,403,206
JBrowse link
G Tnf tumor necrosis factor decreases expression
multiple interactions
ISO 15-keto-5,8,11,13-eicosatetraenoic acid results in decreased expression of TNF mRNA
15-keto-5,8,11,13-eicosatetraenoic acid inhibits the reaction [Lipopolysaccharides results in increased expression of TNF mRNA]
CTD PMID:25450232 NCBI chr17:35,199,367...35,202,007
Ensembl chr17:35,199,381...35,202,007
JBrowse link

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  CHEBI ontology 21552
    chemical entity 21550
      atom 21537
        nonmetal atom 21418
          carbon atom 21133
            organic molecular entity 21133
              olefinic compound 14910
                olefinic fatty acid 647
                  icosatetraenoic acid 334
                    icosa-5,8,11,13-tetraenoic acid 32
                      (5Z,8Z,11Z,13E)-15-HETE + 28
                      15(S)-HPETE + 0
                      15-oxo-ETE + 7
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  CHEBI ontology 21552
    subatomic particle 21537
      composite particle 21537
        hadron 21537
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              atomic nucleus 21537
                atom 21537
                  main group element atom 21442
                    p-block element atom 21442
                      carbon group element atom 21235
                        carbon atom 21133
                          organic molecular entity 21133
                            organic group 19572
                              organic divalent group 19562
                                organodiyl group 19562
                                  carbonyl group 19543
                                    carbonyl compound 19543
                                      carboxylic acid 19118
                                        monocarboxylic acid 18403
                                          fatty acid 16584
                                            unsaturated fatty acid 953
                                              polyunsaturated fatty acid 685
                                                fatty acid 20:4 334
                                                  icosatetraenoic acid 334
                                                    icosa-5,8,11,13-tetraenoic acid 32
                                                      (5Z,8Z,11Z,13E)-15-HETE + 28
                                                      15(S)-HPETE + 0
                                                      15-oxo-ETE + 7
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