1.02011-09-21 00:27:47 UTC2015-07-21 06:57:38 UTCFDB023303AnandamideAnandamide 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-eicosatetraenamide5,8,11,14-EicosatetraenoylethanolamideAEAAnandamideAnandamide (20.4, n-6)Anandamide(20:4, n-6)Arachidonic acid n-(hydroxyethyl)amideArachidonoyl ethanolamideArachidonylethanolamideN-(2-hydroxyethyl)-5,8,11,14-Eicosatetraenamide (all-Z)N-(2-Hydroxyethyl)anachidonamideN-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineN-(5Z,8Z,11Z,14Z-icosatetraenoyl)-ethanolamideN-arachidonoyl ethanolamineN-Arachidonoyl-2-hydroxyethylamideC22H37NO2347.5347347.282429433N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acidN-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid94421-68-8CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCOInChI=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 acidsOrganic compoundsOrganic acids and derivativesCarboximidic acids and derivativesCarboximidic acidsAliphatic acyclic compoundsAlkanolaminesHydrocarbon derivativesOrganopnictogen compoundsPrimary alcoholsPropargyl-type 1,3-dipolar organic compoundsAlcoholAliphatic acyclic compoundAlkanolamineCarboximidic acidHydrocarbon derivativeOrganic 1,3-dipolar compoundOrganic nitrogen compoundOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPrimary alcoholPropargyl-type 1,3-dipolar organic compounda monocarboxylic-acid-amidean <i>N</i>-acylethanolamineSolidlogp6.22logs-6.14solubility2.51e-04 g/llogp6.13pka_strongest_acidic6.37pka_strongest_basic4.34iupacN-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acidaverage_mass347.5347mono_mass347.282429433smilesCCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCOformulaC22H37NO2inchiInChI=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)inchikeyLGEQQWMQCRIYKG-UHFFFAOYSA-Npolar_surface_area52.82refractivity113.49polarizability42.69rotatable_bond_count16acceptor_count3donor_count2physiological_charge0formal_charge0Specdb::MsMs3412046Specdb::MsMs3412047Specdb::MsMs3412048Specdb::MsMs3412049Specdb::MsMs3412050Specdb::MsMs3412051Specdb::CMs108568Specdb::CMs121165Specdb::CMs833541Specdb::CMs833542Specdb::CMs833543Specdb::CMs833544Specdb::CMs833545Specdb::CMs833546HMDB040802700#<Reference:0x0000555675b8fda0>#<Reference:0x0000555675b8fb48>#<Reference:0x0000555675b8f850>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Abhydrolase domain-containing protein 4Q8TB40ABHD4Fatty-acid amide hydrolase 1O00519FAAHFatty-acid amide hydrolase 2Q6GMR7FAAH2