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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:lipoxin A4
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Accession:CHEBI:6498 term browser browse the term
Definition:A C20 hydroxy fatty acid having (5S)-, (6R)- and (15S)-hydroxy groups as well as (7E)- (9E)-, (11Z)- and (13E)-double bonds.
Synonyms:related_synonym: (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxy-7,9,11,13-eicosatetraenoic acid;   (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyeicosa-7,9,11,13-tetraenoic acid;   (7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoic acid;   5(S),6(R),15(S)-trihydroxyeicosa-7E,9E,11Z,13E-tetraenoic acid;   5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid;   5S,6R,15S-trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid;   5S,6R-LipoxinA4;   6R-LXA4;   Formula=C20H32O5;   InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1;   InChIKey=IXAQOQZEOGMIQS-SSQFXEBMSA-N;   LXA4;   SMILES=CCCCC[C@H](O)\\C=C\\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O
 xref: HMDB:HMDB0004385;   KEGG:C06314;   LIPID_MAPS_instance:LMFA03040001
 xref_mesh: MESH:C040527
 xref: PMID:20435922;   PMID:20802423;   PMID:20833483;   PMID:20950211;   PMID:20959513;   PMID:21263017;   PMID:8690917;   Reaxys:4698639
 cyclic_relationship: is_conjugate_acid_of CHEBI:67026


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lipoxin A4 term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ahr aryl hydrocarbon receptor multiple interactions ISO AHR affects the reaction [lipoxin A4 results in increased expression of SOCS2 mRNA] CTD PMID:16415877 NCBI chr 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
JBrowse link
G Alox5 arachidonate 5-lipoxygenase multiple interactions
affects abundance
EXP zileuton inhibits the reaction [ALOX5 protein affects the abundance of lipoxin A4] CTD PMID:15326064 NCBI chr 4:148,398,004...148,446,308
Ensembl chr 4:148,398,892...148,446,303
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions ISO lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased expression of BAX protein] CTD PMID:23063943 NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions ISO lipoxin A4 inhibits the reaction [Lipopolysaccharides results in decreased expression of BCL2 protein] CTD PMID:23063943 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Cxcl2 C-X-C motif chemokine ligand 2 multiple interactions ISO lipoxin A4 analog inhibits the reaction [TNF protein results in increased secretion of CXCL2 protein] CTD PMID:10377187 NCBI chr14:18,731,346...18,733,391
Ensembl chr14:18,731,378...18,733,391
JBrowse link
G Fpr2 formyl peptide receptor 2 multiple interactions
increases activity
ISO
EXP
[Aspirin results in increased abundance of lipoxin A4] which results in increased expression of FPR2; lipoxin A4 analog binds to and results in decreased activity of FPR2 protein
lipoxin A4 results in increased activity of FPR2
lipoxin A4 inhibits the reaction [lipopolysaccharide, E coli O55-B5 results in increased expression of FPR2 mRNA]
CTD PMID:12594298, PMID:19597002, PMID:21765620 NCBI chr 1:59,800,558...59,809,507
Ensembl chr 1:59,800,984...59,802,401
JBrowse link
G Hmox1 heme oxygenase 1 increases expression
multiple interactions
EXP lipoxin A4 results in increased expression of HMOX1 mRNA; lipoxin A4 results in increased expression of HMOX1 protein
lipoxin A4 promotes the reaction [NFE2L2 protein binds to HMOX1 enhancer]
CTD PMID:23826208 NCBI chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
JBrowse link
G Icam1 intercellular adhesion molecule 1 affects response to substance ISO ICAM1 protein affects the susceptibility to lipoxin A4 CTD PMID:7602232 NCBI chr 8:22,035,287...22,047,049
Ensembl chr 8:22,035,256...22,047,059
JBrowse link
G Il1b interleukin 1 beta decreases expression
multiple interactions
decreases secretion
ISO lipoxin A4 analog results in decreased expression of IL1B protein
butyloxycarbonyl-phenylalanyl-leucyl-phenylalanyl-leucyl-phenylalanine inhibits the reaction [lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased expression of IL1B mRNA]]; butyloxycarbonyl-phenylalanyl-leucyl-phenylalanyl-leucyl-phenylalanine inhibits the reaction [lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased secretion of IL1B protein]]; lipoxin A4 analog inhibits the reaction [TNF protein results in increased secretion of IL1B protein]; lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased expression of IL1B mRNA]; lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased secretion of IL1B protein]
lipoxin A4 analog results in decreased secretion of IL1B protein
lipoxin A4 analog inhibits the reaction [TNF protein results in increased expression of IL1B mRNA]; lipoxin A4 analog inhibits the reaction [TNF protein results in increased secretion of IL1B protein]; lipoxin A4 inhibits the reaction [TNF protein results in increased secretion of IL1B protein]
CTD PMID:10377187, PMID:21659618, PMID:21831303 NCBI chr 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
JBrowse link
G Il4 interleukin 4 increases secretion ISO lipoxin A4 analog results in increased secretion of IL4 protein CTD PMID:10377187 NCBI chr10:38,963,979...38,969,531
Ensembl chr10:38,963,979...38,969,531
JBrowse link
G Il6 interleukin 6 multiple interactions ISO lipoxin A4 inhibits the reaction [3,4,5,3',4'-pentachlorobiphenyl results in increased secretion of IL6 protein] CTD PMID:27663891 NCBI chr 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased phosphorylation of MAPK1 protein] CTD PMID:21831303 NCBI chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions ISO lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased phosphorylation of MAPK3 protein] CTD PMID:21831303 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 affects localization
multiple interactions
EXP lipoxin A4 affects the localization of NFE2L2 protein
lipoxin A4 promotes the reaction [NFE2L2 protein binds to HMOX1 enhancer]
CTD PMID:23826208 NCBI chr 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
JBrowse link
G Nfkbia NFKB inhibitor alpha multiple interactions ISO lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased degradation of NFKBIA protein] CTD PMID:21831303 NCBI chr 6:76,267,227...76,270,457
Ensembl chr 6:76,267,228...76,270,457
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO butyloxycarbonyl-phenylalanyl-leucyl-phenylalanyl-leucyl-phenylalanine inhibits the reaction [lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 mRNA]]; butyloxycarbonyl-phenylalanyl-leucyl-phenylalanyl-leucyl-phenylalanine inhibits the reaction [lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein]]; lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 mRNA]; lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein] CTD PMID:21831303 NCBI chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
JBrowse link
G Pdgfb platelet derived growth factor subunit B multiple interactions ISO lipoxin A4 affects the reaction [PDGFB protein results in increased phosphorylation of PDGFRB protein]; PDGFB protein promotes the reaction [lipoxin A4 results in decreased phosphorylation of PDGFRB protein] CTD PMID:12223454, PMID:20709806 NCBI chr 7:121,215,458...121,233,092
Ensembl chr 7:121,214,628...121,232,741
JBrowse link
G Pdgfrb platelet derived growth factor receptor beta multiple interactions
decreases phosphorylation
ISO lipoxin A4 affects the reaction [PDGFB protein results in increased phosphorylation of PDGFRB protein]; lipoxin A4 inhibits the reaction [Leukotriene D4 results in increased activity of PDGFRB protein]; PDGFB protein promotes the reaction [lipoxin A4 results in decreased phosphorylation of PDGFRB protein] CTD PMID:12223454, PMID:20709806 NCBI chr18:56,364,586...56,406,381
Ensembl chr18:56,364,620...56,406,381
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions EXP lipoxin A4 binds to and results in increased activity of PPARG protein CTD PMID:19321784 NCBI chr 4:147,274,055...147,399,383
Ensembl chr 4:147,274,107...147,399,380
JBrowse link
G Ptafr platelet-activating factor receptor multiple interactions ISO [WEB 2086 binds to and results in decreased activity of PTAFR protein] which results in decreased susceptibility to lipoxin A4 CTD PMID:7602232 NCBI chr 5:150,746,284...150,775,675
Ensembl chr 5:150,754,021...150,775,672
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions
affects abundance
EXP [lipoxin A4 co-treated with lipopolysaccharide, E coli O55-B5] results in increased expression of PTGS2 protein; Celecoxib inhibits the reaction [PTGS2 protein affects the abundance of lipoxin A4]; lipoxin A4 inhibits the reaction [lipopolysaccharide, E coli O55-B5 results in increased expression of PTGS2 protein] CTD PMID:15326064, PMID:21765620 NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO lipoxin A4 inhibits the reaction [Lipopolysaccharides affects the localization of RELA protein]
lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased localization of RELA protein]
CTD PMID:21831303, PMID:23063943 NCBI chr 1:220,992,770...221,003,249
Ensembl chr 1:220,992,770...221,003,249
JBrowse link
G Selp selectin P affects response to substance ISO SELP protein affects the susceptibility to lipoxin A4 CTD PMID:7602232 NCBI chr13:82,428,914...82,464,629
Ensembl chr13:82,429,063...82,464,628
JBrowse link
G Socs2 suppressor of cytokine signaling 2 multiple interactions
increases expression
ISO AHR affects the reaction [lipoxin A4 results in increased expression of SOCS2 mRNA]; butyloxycarbonyl-phenylalanyl-leucyl-phenylalanyl-leucyl-phenylalanine inhibits the reaction [lipoxin A4 results in increased expression of SOCS2 mRNA]
lipoxin A4 results in increased expression of SOCS2 mRNA; lipoxin A4 results in increased expression of SOCS2 protein
CTD PMID:16415877 NCBI chr 7:36,495,496...36,500,878
Ensembl chr 7:36,495,480...36,499,784
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO lipoxin A4 analog inhibits the reaction [TNF protein results in increased expression of IL1B mRNA]; lipoxin A4 analog inhibits the reaction [TNF protein results in increased secretion of IL1B protein]; lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased expression of TNF mRNA]; lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased secretion of TNF protein]; lipoxin A4 inhibits the reaction [TNF protein results in increased secretion of IL1B protein]
butyloxycarbonyl-phenylalanyl-leucyl-phenylalanyl-leucyl-phenylalanine inhibits the reaction [lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased expression of TNF mRNA]]; butyloxycarbonyl-phenylalanyl-leucyl-phenylalanyl-leucyl-phenylalanine inhibits the reaction [lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased secretion of TNF protein]]; lipoxin A4 analog inhibits the reaction [TNF protein results in increased secretion of CXCL2 protein]; lipoxin A4 analog inhibits the reaction [TNF protein results in increased secretion of IL1B protein]; lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased expression of TNF mRNA]; lipoxin A4 inhibits the reaction [Lipopolysaccharides results in increased secretion of TNF protein]
CTD PMID:10377187, PMID:21575454, PMID:21831303, PMID:23063943 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19810
    role 19758
      biological role 19758
        biochemical role 19304
          metabolite 19285
            lipoxin A4 25
              20-hydroxylipoxin A4 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19810
    subatomic particle 19808
      composite particle 19808
        hadron 19808
          baryon 19808
            nucleon 19808
              atomic nucleus 19808
                atom 19808
                  main group element atom 19696
                    p-block element atom 19696
                      carbon group element atom 19599
                        carbon atom 19588
                          organic molecular entity 19588
                            organic group 18527
                              organic divalent group 18520
                                organodiyl group 18520
                                  carbonyl group 18427
                                    carbonyl compound 18427
                                      carboxylic acid 18108
                                        monocarboxylic acid 17475
                                          fatty acid 15994
                                            unsaturated fatty acid 924
                                              polyunsaturated fatty acid 664
                                                fatty acid 20:4 313
                                                  icosatetraenoic acid 313
                                                    icosa-5,8,11,14-tetraenoic acid 264
                                                      arachidonic acid 264
                                                        lipoxin 25
                                                          lipoxin A4 25
                                                            20-hydroxylipoxin A4 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.