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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:anandamide
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Accession:CHEBI:2700 term browser browse the term
Definition:An N-(polyunsaturated fatty acyl)ethanolamine resulting from the formal condensation of carboxy group of arachidonic acid with amino group of ethanolamine.
Synonyms:exact_synonym: (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
 related_synonym: (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide;   (all-Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide;   AEA;   Anandamide(20:4, N-6);   Arachidonic acid N-(hydroxyethyl)amide;   Arachidonylethanolamide;   Formula=C22H37NO2;   InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-;   InChIKey=LGEQQWMQCRIYKG-DOFZRALJSA-N;   N-(2-Hydroxyethyl)anachidonamide;   N-(5Z,8Z,11Z,14Z-eicosatetraenoyl) ethanolamine;   N-(5Z,8Z,11Z,14Z-icosatetraenoyl)-ethanolamide;   N-arachidonoyl ethanolamine;   N-arachidonoyl-2-hydroxyethylamide;   N-arachidonoylethanolamine;   SMILES=C(CCC)C/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCC(NCCO)=O;   arachidonoyl ethanolamide
 alt_id: CHEBI:88116
 xref: Beilstein:7079463;   CAS:94421-68-8;   HMDB:HMDB0004080;   KEGG:C11695;   LIPID_MAPS_instance:LMFA08040001
 xref_mesh: MESH:C078814
 xref: MetaCyc:CPD-7598;   PMID:15047233;   PMID:15797258;   PMID:15997233;   PMID:16118355;   PMID:16957004;   PMID:18691603;   PMID:19330032;   Reaxys:7079463;   Wikipedia:Anandamide


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anandamide term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G App amyloid beta precursor protein decreases response to substance EXP anandamide results in decreased susceptibility to APP protein CTD PMID:22233683 NCBI chr11:24,425,013...24,641,872
Ensembl chr11:24,425,005...24,641,858
JBrowse link
G Bdkrb1 bradykinin receptor B1 multiple interactions
decreases activity
ISO AM 251 inhibits the reaction [anandamide results in decreased activity of BDKRB1 protein] CTD PMID:19022239 NCBI chr 6:129,437,423...129,441,553
Ensembl chr 6:129,438,158...129,440,574
JBrowse link
G Cd36 CD36 molecule increases expression ISO anandamide results in increased expression of CD36 mRNA; anandamide results in increased expression of CD36 protein CTD PMID:17360047 NCBI chr 4:14,150,309...14,191,498
Ensembl chr 4:14,001,761...14,249,749
JBrowse link
G Cnr1 cannabinoid receptor 1 affects activity
affects binding
increases activity
multiple interactions
ISO
EXP
anandamide affects the activity of CNR1 protein
anandamide binds to CNR1 protein
anandamide results in increased activity of CNR1 protein
2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [anandamide results in increased activity of CNR1]; CNR1 affects the reaction [TRPV1 affects the susceptibility to anandamide]; Pertussis Toxin inhibits the reaction [anandamide results in increased activity of CNR1]; rimonabant inhibits the reaction [anandamide results in increased activity of CNR1]
[anandamide binds to and results in increased activity of CNR1 protein] inhibits the reaction [Lipopolysaccharides results in increased abundance of Nitric Oxide]; CNR1 gene mutant form inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]; CNR1 gene mutant form inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]; rimonabant inhibits the reaction [[anandamide binds to and results in increased activity of CNR1 protein] inhibits the reaction [Lipopolysaccharides results in increased transport of Nitric Oxide]]; SR 144528 inhibits the reaction [[anandamide binds to and results in increased activity of CNR1 protein] inhibits the reaction [Lipopolysaccharides results in increased transport of Nitric Oxide]]
CTD PMID:10871313, PMID:11408034, PMID:11891798, PMID:12657697, PMID:14504685, PMID:15453094, PMID:17557913, PMID:19147270 NCBI chr 5:49,307,584...49,333,064
Ensembl chr 5:49,311,030...49,333,056
JBrowse link
G Cnr2 cannabinoid receptor 2 affects activity
multiple interactions
affects binding
ISO
EXP
anandamide affects the activity of CNR2 protein
anandamide binds to and results in increased activity of CNR2 protein; CNR2 affects the reaction [TRPV1 affects the susceptibility to anandamide]
anandamide binds to CNR2 protein
CTD PMID:10617657, PMID:10688601, PMID:15453094, PMID:19147270 NCBI chr 5:154,242,010...154,268,126
Ensembl chr 5:154,260,062...154,268,126
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO anandamide results in increased expression of DDIT3 mRNA CTD PMID:21949157 NCBI chr 7:70,578,564...70,585,074
Ensembl chr 7:70,580,198...70,585,084
JBrowse link
G F3 coagulation factor III, tissue factor multiple interactions
increases expression
ISO anandamide promotes the reaction [IL1B protein results in increased expression of F3 protein]
anandamide results in increased expression of F3 protein
CTD PMID:27556861 NCBI chr 2:225,310,686...225,322,281
Ensembl chr 2:225,310,624...225,322,272
JBrowse link
G Faah fatty acid amide hydrolase increases degradation
multiple interactions
affects expression
ISO
EXP
FAAH results in increased degradation of anandamide
FAAH protein results in increased degradation of anandamide
[Chlorpyrifos results in decreased activity of FAAH protein] which results in increased abundance of anandamide; [Lipopolysaccharides results in decreased expression of FAAH protein] which results in increased abundance of anandamide; Nitroglycerin promotes the reaction [FAAH protein results in increased degradation of anandamide]
anandamide affects the expression of FAAH protein
[nimesulide results in decreased expression of PTGS2] promotes the reaction [FAAH affects the metabolism of anandamide]
CTD PMID:11556820, PMID:16131814, PMID:16886060, PMID:19515121, PMID:20702753, PMID:23761300, PMID:26642910 NCBI chr 5:134,852,899...134,872,095
Ensembl chr 5:134,852,875...134,871,775
JBrowse link
G Faahl fatty-acid amide hydrolase-like increases degradation
multiple interactions
affects expression
ISO FAAH results in increased degradation of anandamide
[nimesulide results in decreased expression of PTGS2] promotes the reaction [FAAH affects the metabolism of anandamide]
anandamide affects the expression of FAAH protein
CTD PMID:16131814, PMID:16886060, PMID:20702753 NCBI chr 5:134,330,204...134,349,400
Ensembl chr 5:134,331,929...134,348,995
JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit multiple interactions
increases expression
EXP anandamide inhibits the reaction [Nitroglycerin results in increased expression of FOS protein]; capsazepine inhibits the reaction [anandamide results in increased expression of FOS protein]; resiniferatoxin inhibits the reaction [anandamide results in increased expression of FOS protein]
anandamide results in increased expression of FOS; anandamide results in increased expression of FOS protein
CTD PMID:9748483, PMID:15601931, PMID:19515121 NCBI chr 6:109,300,433...109,303,299
Ensembl chr 6:109,300,433...109,303,299
JBrowse link
G Ifng interferon gamma multiple interactions ISO anandamide affects the reaction [[Lipopolysaccharides co-treated with IFNG] results in increased secretion of TNF]; anandamide inhibits the reaction [[Lipopolysaccharides co-treated with IFNG] results in increased secretion of IL1B] CTD PMID:12813001 NCBI chr 7:61,337,383...61,341,419
Ensembl chr 7:61,337,381...61,341,419
JBrowse link
G Igf1 insulin-like growth factor 1 increases expression ISO anandamide results in increased expression of IGF1 protein CTD PMID:17307377 NCBI chr 7:28,412,123...28,491,815
Ensembl chr 7:28,412,198...28,486,609
JBrowse link
G Il12b interleukin 12B multiple interactions ISO [OMDM-1 cpd co-treated with anandamide] inhibits the reaction [Lipopolysaccharides results in increased secretion of IL12B protein]; anandamide inhibits the reaction [Lipopolysaccharides results in increased secretion of IL12B protein] CTD PMID:15748152 NCBI chr10:30,034,447...30,048,774
Ensembl chr10:30,038,709...30,048,085
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO anandamide inhibits the reaction [Lipopolysaccharides results in increased secretion of IL1B protein]
anandamide inhibits the reaction [[Lipopolysaccharides co-treated with IFNG] results in increased secretion of IL1B]; anandamide promotes the reaction [IL1B protein results in increased expression of F3 protein]
CTD PMID:12813001, PMID:15748152, PMID:27556861 NCBI chr 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
JBrowse link
G Lep leptin decreases abundance
decreases activity
decreases transport
ISO LEP protein results in decreased abundance of anandamide
LEP protein results in decreased activity of anandamide
LEP protein results in decreased transport of anandamide
CTD PMID:16154199 NCBI chr 4:56,337,695...56,351,818
Ensembl chr 4:56,337,695...56,351,818
JBrowse link
G Map2k1 mitogen activated protein kinase kinase 1 multiple interactions EXP 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAP2K1 protein]; anandamide results in increased phosphorylation of and results in increased activity of MAP2K1 protein; U 0126 inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAP2K1 protein] CTD PMID:12657697 NCBI chr 8:69,134,218...69,722,573
Ensembl chr 8:69,134,223...69,164,758
JBrowse link
G Map2k2 mitogen activated protein kinase kinase 2 multiple interactions EXP 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAP2K2 protein]; anandamide results in increased phosphorylation of and results in increased activity of MAP2K2 protein; U 0126 inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAP2K2 protein] CTD PMID:12657697 NCBI chr 7:11,458,971...11,478,520
Ensembl chr 7:11,458,967...11,478,489
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
increases phosphorylation
ISO
EXP
anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein; CNR1 gene mutant form inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]
anandamide results in increased phosphorylation of MAPK1 protein
2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]; 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]; 4-amino-5-(4-methylphenyl)-7-(tert-butyl)pyrazolo(3,4-d)pyrimidine inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]; AM 251 inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]; anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein; Hydrogen Peroxide promotes the reaction [anandamide results in increased phosphorylation of MAPK1 protein]; JTE 907 inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]; Pertussis Toxin inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]; wortmannin inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]
8-Bromo Cyclic Adenosine Monophosphate inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]; anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein; Rimonabant inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK1 protein]
CTD PMID:12657697, PMID:19477951, PMID:21179406 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
increases phosphorylation
ISO
EXP
anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein; CNR1 gene mutant form inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]
anandamide results in increased phosphorylation of MAPK3 protein
2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]; 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]; 4-amino-5-(4-methylphenyl)-7-(tert-butyl)pyrazolo(3,4-d)pyrimidine inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]; AM 251 inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]; anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein; Hydrogen Peroxide promotes the reaction [anandamide results in increased phosphorylation of MAPK3 protein]; JTE 907 inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]; Pertussis Toxin inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]; wortmannin inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]
8-Bromo Cyclic Adenosine Monophosphate inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]; anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein; rimonabant inhibits the reaction [anandamide results in increased phosphorylation of and results in increased activity of MAPK3 protein]
CTD PMID:12657697, PMID:19477951, PMID:21179406 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mmp1 matrix metallopeptidase 1 increases expression ISO anandamide results in increased expression of MMP1 mRNA CTD PMID:16330497 NCBI chr 8:5,703,206...5,723,593
Ensembl chr 8:5,703,206...5,723,591
JBrowse link
G Mmp3 matrix metallopeptidase 3 increases expression ISO anandamide results in increased expression of MMP3 mRNA CTD PMID:16330497 NCBI chr 8:5,676,608...5,698,579
Ensembl chr 8:5,676,665...5,698,579
JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions
increases expression
ISO N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide inhibits the reaction [anandamide results in increased expression of MMP9 mRNA] CTD PMID:16330497 NCBI chr 3:161,413,410...161,421,473
Ensembl chr 3:161,413,298...161,421,520
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO anandamide inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 mRNA]; anandamide inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein] CTD PMID:11891798, PMID:15748152 NCBI chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
JBrowse link
G Ppara peroxisome proliferator activated receptor alpha multiple interactions ISO anandamide binds to and results in increased activity of PPARA protein CTD PMID:17906680 NCBI chr 7:126,618,872...126,687,282
Ensembl chr 7:126,619,196...126,681,752
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions
increases expression
increases metabolic processing
EXP
ISO
[nimesulide results in decreased expression of PTGS2] which results in increased activity of anandamide
anandamide results in increased expression of PTGS2 mRNA; anandamide results in increased expression of PTGS2 protein
PTGS2 results in increased metabolism of anandamide
[nimesulide results in decreased expression of PTGS2] promotes the reaction [FAAH affects the metabolism of anandamide]
CTD PMID:16330497, PMID:17245358, PMID:20702753 NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Timp1 TIMP metallopeptidase inhibitor 1 increases expression
multiple interactions
ISO anandamide results in increased expression of TIMP1 mRNA
N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide inhibits the reaction [anandamide results in increased expression of TIMP1 mRNA]
CTD PMID:16330497 NCBI chr  X:1,364,771...1,369,451
Ensembl chr  X:1,364,786...1,369,384
JBrowse link
G Tnf tumor necrosis factor multiple interactions
increases abundance
EXP
ISO
anandamide inhibits the reaction [lipopolysaccharide, E. coli O26-B6 results in increased expression of TNF protein]
TNF protein results in increased abundance of anandamide
anandamide affects the reaction [[Lipopolysaccharides co-treated with IFNG] results in increased secretion of TNF]
CTD PMID:12509806, PMID:12813001, PMID:20626112 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Trpv1 transient receptor potential cation channel, subfamily V, member 1 multiple interactions
increases response to substance
increases activity
affects response to substance
affects binding
ISO
EXP
3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo(b)(1,4)dioxin-6-yl)acrylamide inhibits the reaction [anandamide promotes the reaction [TRPV1 protein results in increased uptake of Calcium]]; anandamide binds to and results in increased activity of TRPV1 protein; capsazepine inhibits the reaction [anandamide binds to and results in increased activity of TRPV1 protein]; CNR1 affects the reaction [TRPV1 affects the susceptibility to anandamide]; CNR2 affects the reaction [TRPV1 affects the susceptibility to anandamide]; Egtazic Acid inhibits the reaction [anandamide binds to and results in increased activity of TRPV1 protein]; methyl arachidonylfluorophosphonate promotes the reaction [anandamide binds to and results in increased activity of TRPV1 protein]; N-(2-methyl-3-hydroxyphenyl)-5,8,11,14-eicosatetraenamide inhibits the reaction [anandamide binds to and results in increased activity of TRPV1 protein]; Nitroprusside promotes the reaction [anandamide binds to and results in increased activity of TRPV1 protein]; Phenylmethylsulfonyl Fluoride promotes the reaction [anandamide binds to and results in increased activity of TRPV1 protein]; rimonabant inhibits the reaction [anandamide binds to and results in increased activity of TRPV1 protein]
TRPV1 protein results in increased susceptibility to anandamide
anandamide results in increased activity of TRPV1 protein
anandamide binds to TRPV1 protein
3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo(b)(1,4)dioxin-6-yl)acrylamide inhibits the reaction [anandamide promotes the reaction [TRPV1 protein results in increased uptake of Calcium]]; anandamide binds to and results in increased activity of TRPV1 protein; bisindolylmaleimide inhibits the reaction [anandamide results in increased activity of TRPV1 protein]; Eicosapentaenoic Acid inhibits the reaction [anandamide results in increased activity of TRPV1 protein]; Tetradecanoylphorbol Acetate promotes the reaction [anandamide results in increased activity of TRPV1 protein]
CTD PMID:11140687, PMID:11278420, PMID:14504685, PMID:15453094, PMID:15601931, PMID:15615864, PMID:17038422, PMID:17913835, PMID:18550765, PMID:21949157 NCBI chr10:59,799,123...59,824,208
Ensembl chr10:59,799,123...59,824,679
JBrowse link
G Vegfa vascular endothelial growth factor A multiple interactions ISO anandamide results in decreased expression of and results in decreased secretion of VEGFA protein CTD PMID:15313899 NCBI chr 9:17,340,341...17,355,681
Ensembl chr 9:17,340,341...17,355,681
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19792
    role 19738
      biological role 19737
        molecular messenger 18279
          neurotransmitter 10740
            anandamide 29
              N-(20-hydroxyarachidonoyl)ethanolamine 0
              N-[(5Z,11Z,14Z)-8,9-epoxyicosatrienoyl]ethanolamine 0
              N-[(5Z,8Z,11Z)-14,15-epoxyicosatrienoyl]ethanolamine 0
              N-[(5Z,8Z,14Z)-11,12-epoxyicosatrienoyl]ethanolamine 0
              N-[(8Z,11Z,14Z)-5,6-epoxyicosatrienoyl]ethanolamine 0
              N-arachidonoylethanolamine phosphate(2-) 0
              O-oleoylanandamide 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19792
    subatomic particle 19788
      composite particle 19788
        hadron 19788
          baryon 19788
            nucleon 19788
              atomic nucleus 19788
                atom 19788
                  main group element atom 19675
                    p-block element atom 19675
                      carbon group element atom 19571
                        carbon atom 19560
                          organic molecular entity 19560
                            organic group 18508
                              organic divalent group 18501
                                organodiyl group 18501
                                  carbonyl group 18404
                                    carbonyl compound 18404
                                      carboxylic acid 18079
                                        monocarboxylic acid 17425
                                          fatty acid 15860
                                            unsaturated fatty acid 916
                                              polyunsaturated fatty acid 663
                                                fatty acid 20:4 313
                                                  icosatetraenoic acid 313
                                                    icosa-5,8,11,14-tetraenoic acid 264
                                                      arachidonic acid 264
                                                        anandamide 29
                                                          N-(20-hydroxyarachidonoyl)ethanolamine 0
                                                          N-[(5Z,11Z,14Z)-8,9-epoxyicosatrienoyl]ethanolamine 0
                                                          N-[(5Z,8Z,11Z)-14,15-epoxyicosatrienoyl]ethanolamine 0
                                                          N-[(5Z,8Z,14Z)-11,12-epoxyicosatrienoyl]ethanolamine 0
                                                          N-[(8Z,11Z,14Z)-5,6-epoxyicosatrienoyl]ethanolamine 0
                                                          N-arachidonoylethanolamine phosphate(2-) 0
                                                          O-oleoylanandamide 0
paths to the root

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.