1.0 2011-09-21 00:27:47 UTC 2015-07-21 06:57:38 UTC FDB023303 Anandamide Anandamide is a highly potent endogenous agonist of the cannabinoid CB1 and CB2 receptors. CB1 receptors are predominantly found in the central nervous system (CNS) where they mainly mediate the psychotropic effects of Tetrahydrocannabinol (THC) and endocannabinoids, whereas the expression of the CB2 receptor is thought to be restricted to cells of the immune system. It was suggested that AEA might inhibit tumor cell proliferation or induce apoptosis independently of CB1 and CB2 receptors, via interaction with the type 1 vanilloid receptor (VR1). VR1 is an ion channel expressed almost exclusively by sensory neurons, activated by pH, noxious heat (>48 degree centigrade) and plant toxins and is thought to play an important role in nociception. Cervical cancer cells are sensitive to AEA-induced apoptosis via VR1 that is aberrantly expressed in vitro and in vivo while CB1 and CB2 receptors play a protective role. (PMID 15047233) Novel prostaglandins (prostaglandin glycerol esters and prostaglandin ethanolamides) are COX-2 oxidative metabolites of endogenous cannabinoids (such as Anandamide). Recent evidence suggests that these new types of prostaglandins are likely novel signaling mediators involved in synaptic transmission and plasticity. (PMID 16957004) [HMDB] (5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide (all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide 5,8,11,14-Eicosatetraenoylethanolamide AEA Anandamide Anandamide (20.4, n-6) Anandamide(20:4, n-6) Arachidonic acid n-(hydroxyethyl)amide Arachidonoyl ethanolamide Arachidonylethanolamide N-(2-hydroxyethyl)-5,8,11,14-Eicosatetraenamide (all-Z) 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 C22H37NO2 347.5347 347.282429433 N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid 94421-68-8 CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO 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) LGEQQWMQCRIYKG-UHFFFAOYSA-N belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). Carboximidic acids Organic compounds Organic acids and derivatives Carboximidic acids and derivatives Carboximidic acids Aliphatic acyclic compounds Alkanolamines Hydrocarbon derivatives Organopnictogen compounds Primary alcohols Propargyl-type 1,3-dipolar organic compounds Alcohol Aliphatic acyclic compound Alkanolamine Carboximidic acid Hydrocarbon derivative Organic 1,3-dipolar compound Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary alcohol Propargyl-type 1,3-dipolar organic compound a monocarboxylic-acid-amide an <i>N</i>-acylethanolamine Solid logp 6.22 ALOGPS logs -6.14 ALOGPS solubility 2.51e-04 g/l ALOGPS logp 6.13 ChemAxon pka_strongest_acidic 6.37 ChemAxon pka_strongest_basic 4.34 ChemAxon iupac N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid ChemAxon average_mass 347.5347 ChemAxon mono_mass 347.282429433 ChemAxon smiles CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO ChemAxon formula C22H37NO2 ChemAxon inchi 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) ChemAxon inchikey LGEQQWMQCRIYKG-UHFFFAOYSA-N ChemAxon polar_surface_area 52.82 ChemAxon refractivity 113.49 ChemAxon polarizability 42.69 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 3412046 Specdb::MsMs 3412047 Specdb::MsMs 3412048 Specdb::MsMs 3412049 Specdb::MsMs 3412050 Specdb::MsMs 3412051 Specdb::CMs 108568 Specdb::CMs 121165 Specdb::CMs 833541 Specdb::CMs 833542 Specdb::CMs 833543 Specdb::CMs 833544 Specdb::CMs 833545 Specdb::CMs 833546 HMDB04080 2700 #<Reference:0x000055ce32118ba8> #<Reference:0x000055ce321189f0> #<Reference:0x000055ce32118838> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Abhydrolase domain-containing protein 4 Q8TB40 ABHD4 Fatty-acid amide hydrolase 1 O00519 FAAH Fatty-acid amide hydrolase 2 Q6GMR7 FAAH2