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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 10:27:48 UTC
Update Date2022-07-14 23:24:51 UTC
HMDB IDHMDB0004080
Secondary Accession Numbers
  • HMDB04080
Metabolite Identification
Common NameAnandamide
DescriptionAnandamide, also known as arachidonoylethanolamide (AEA), 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 tumour 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 signalling mediators involved in synaptic transmission and plasticity (PMID: 16957004 ).
Structure
Data?1657841091
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamideChEBI
(all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamideChEBI
AEAChEBI
Anandamide (20.4, N-6)ChEBI
Anandamide(20:4, N-6)ChEBI
Arachidonic acid N-(hydroxyethyl)amideChEBI
Arachidonoyl ethanolamideChEBI
ArachidonylethanolamideChEBI
N-(2-Hydroxyethyl)anachidonamideChEBI
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-ethanolamineChEBI
N-(5Z,8Z,11Z,14Z-Icosatetraenoyl)-ethanolamideChEBI
N-Arachidonoyl ethanolamineChEBI
N-Arachidonoyl-2-hydroxyethylamideChEBI
N-ArachidonoylethanolamineChEBI
Arachidonate N-(hydroxyethyl)amideGenerator
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl) ethanolamineHMDB
5,8,11,14-EicosatetraenoylethanolamideHMDB
N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide (all-Z)HMDB
N-(2-Hydroxyethyl)arachidonamideHMDB
Anandamide (20.4,N-6)HMDB
ArachidonoylethanolamideHMDB
N-ArachidonoylethanolamideHMDB
AnandamideMeSH
N-(2-Hydroxyethyl)arachidonylamideHMDB
N-ArachidonylethanolamideHMDB
N-ArachidonylethanolamineHMDB
AEA(22:6)HMDB
Acylethanolamine 22:6HMDB
Chemical FormulaC22H37NO2
Average Molecular Weight347.5347
Monoisotopic Molecular Weight347.282429433
IUPAC Name(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Traditional Nameanandamide
CAS Registry Number94421-68-8
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO
InChI Identifier
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-
InChI KeyLGEQQWMQCRIYKG-DOFZRALJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentN-acylethanolamines
Alternative Parents
Substituents
  • N-acylethanolamine
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00047 g/LALOGPS
logP5.98ALOGPS
logP5.31ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)15.44ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity112.97 m³·mol⁻¹ChemAxon
Polarizability43.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+196.51531661259
DarkChem[M-H]-196.33531661259
DeepCCS[M+H]+191.62430932474
DeepCCS[M-H]-189.26630932474
DeepCCS[M-2H]-222.31130932474
DeepCCS[M+Na]+197.75630932474
AllCCS[M+H]+193.832859911
AllCCS[M+H-H2O]+191.232859911
AllCCS[M+NH4]+196.232859911
AllCCS[M+Na]+196.932859911
AllCCS[M-H]-192.232859911
AllCCS[M+Na-2H]-194.432859911
AllCCS[M+HCOO]-197.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AnandamideCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO3375.1Standard polar33892256
AnandamideCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO2576.9Standard non polar33892256
AnandamideCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO2849.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Anandamide,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C2863.5Semi standard non polar33892256
Anandamide,1TMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C2799.1Semi standard non polar33892256
Anandamide,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2853.6Semi standard non polar33892256
Anandamide,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2908.6Standard non polar33892256
Anandamide,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2886.9Standard polar33892256
Anandamide,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C(C)(C)C3111.6Semi standard non polar33892256
Anandamide,1TBDMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C3049.8Semi standard non polar33892256
Anandamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3350.0Semi standard non polar33892256
Anandamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3257.3Standard non polar33892256
Anandamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2940.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Anandamide GC-EI-TOF (Non-derivatized)splash10-0gb9-1910000000-79c55260280d43c9a9002017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Anandamide GC-EI-TOF (Non-derivatized)splash10-0fs7-5900000000-75831770c51e1d2f739d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Anandamide GC-EI-TOF (Non-derivatized)splash10-0gb9-1910000000-79c55260280d43c9a9002018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Anandamide GC-EI-TOF (Non-derivatized)splash10-0fs7-5900000000-75831770c51e1d2f739d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anandamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-02a5-7493000000-c585906fb5c6d8aa4ff32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anandamide GC-MS (1 TMS) - 70eV, Positivesplash10-0fki-9353100000-6c635dea7003727f3b832017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anandamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Anandamide 10V, Positive-QTOFsplash10-0002-1029000000-acb4551dcc9e3f6e05dd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anandamide 40V, Positive-QTOFsplash10-03xr-9000000000-45148e922a9fd54fabf52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anandamide 20V, Positive-QTOFsplash10-03di-9230000000-c1ae6b0473246ef09b542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anandamide 40V, Positive-QTOFsplash10-03xr-9000000000-100fb9f29334308faa9d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 10V, Positive-QTOFsplash10-01ot-5149000000-76b6af47eca436d3e5ec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 20V, Positive-QTOFsplash10-03dl-9131000000-069d65af4be10e925d422017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 40V, Positive-QTOFsplash10-03dl-9230000000-3590307e1cf3aab766892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 10V, Negative-QTOFsplash10-0002-0009000000-004521084d25577be5fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 20V, Negative-QTOFsplash10-01r2-5019000000-1c63bb1751f58bf91f0c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 40V, Negative-QTOFsplash10-0006-9010000000-161a34c3d66caea4a2932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 10V, Positive-QTOFsplash10-01ot-9328000000-b4562c25b6933ac7a7ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 20V, Positive-QTOFsplash10-03dl-9000000000-4d45bc23e3d763bd083b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 40V, Positive-QTOFsplash10-03dl-9100000000-ed96624588d13e15a5bf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 10V, Negative-QTOFsplash10-0002-0009000000-a3f88dce43caba26e0b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 20V, Negative-QTOFsplash10-0002-5129000000-5f007c24785520e490c52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anandamide 40V, Negative-QTOFsplash10-052f-9010000000-868cfda7283947a9fbc42021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.008 +/- 0.016 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.99 +/- 5.39 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.12 +/- 1.2 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.01165 +/- 0.00753 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.00255 +/- 0.00178 uMAdult (>18 years old)BothEpilepsy details
Associated Disorders and Diseases
Disease References
Epilepsy
  1. Romigi A, Bari M, Placidi F, Marciani MG, Malaponti M, Torelli F, Izzi F, Prosperetti C, Zannino S, Corte F, Chiaramonte C, Maccarrone M: Cerebrospinal fluid levels of the endocannabinoid anandamide are reduced in patients with untreated newly diagnosed temporal lobe epilepsy. Epilepsia. 2010 May;51(5):768-72. doi: 10.1111/j.1528-1167.2009.02334.x. Epub 2009 Oct 8. [PubMed:19817812 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023303
KNApSAcK IDNot Available
Chemspider ID4445241
KEGG Compound IDC11695
BioCyc IDCPD-7598
BiGG IDNot Available
Wikipedia LinkAnandamide
METLIN IDNot Available
PubChem Compound5281969
PDB IDNot Available
ChEBI ID2700
Food Biomarker OntologyNot Available
VMH IDC11695
MarkerDB IDMDB00000439
Good Scents IDNot Available
References
Synthesis ReferenceQi, Longwu; Meijler, Michael M.; Lee, Sang-Hyeup; Sun, Chengzao; Janda, Kim D. Solid-Phase Synthesis of Anandamide Analogues. Organic Letters (2004), 6(10), 1673-1675.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Felder CC, Nielsen A, Briley EM, Palkovits M, Priller J, Axelrod J, Nguyen DN, Richardson JM, Riggin RM, Koppel GA, Paul SM, Becker GW: Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. FEBS Lett. 1996 Sep 16;393(2-3):231-5. [PubMed:8814296 ]
  2. Contassot E, Tenan M, Schnuriger V, Pelte MF, Dietrich PY: Arachidonyl ethanolamide induces apoptosis of uterine cervix cancer cells via aberrantly expressed vanilloid receptor-1. Gynecol Oncol. 2004 Apr;93(1):182-8. [PubMed:15047233 ]
  3. Sang N, Chen C: Lipid signaling and synaptic plasticity. Neuroscientist. 2006 Oct;12(5):425-34. [PubMed:16957004 ]
  4. Anton M, Rodriguez-Gonzalez A, Rodriguez-Rojo IC, Pastor A, Correas A, Serrano A, Ballesta A, Alen F, Gomez de Heras R, de la Torre R, Rodriguez de Fonseca F, Orio L: Increased plasma oleoylethanolamide and palmitoleoylethanolamide levels correlate with inflammatory changes in alcohol binge drinkers: the case of HMGB1 in women. Addict Biol. 2018 Nov;23(6):1242-1250. doi: 10.1111/adb.12580. Epub 2017 Nov 27. [PubMed:29178411 ]

Enzymes

General function:
Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates.
Gene Name:
FAAH
Uniprot ID:
O00519
Molecular weight:
63065.28
Reactions
Anandamide + Water → Arachidonic acid + Ethanolaminedetails
General function:
Involved in hydrolase activity
Specific function:
Lysophospholipase selective for N-acyl phosphatidylethanolamine (NAPE). Contributes to the biosynthesis of N-acyl ethanolamines, including the endocannabinoid anandamide by hydrolyzing the sn-1 and sn-2 acyl chains from N-acyl phosphatidylethanolamine (NAPE) generating glycerophospho-N-acyl ethanolamine (GP-NAE), an intermediate for N-acyl ethanolamine biosynthesis. Hydrolyzes substrates bearing saturated, monounsaturated, polyunsaturated N-acyl chains. Shows no significant activity towards other lysophospholipids, including lysophosphatidylcholine, lysophosphatidylethanolamine and lysophosphatidylserine
Gene Name:
ABHD4
Uniprot ID:
Q8TB40
Molecular weight:
38794.1
General function:
Involved in metal ion binding
Specific function:
Hydrolyzes N-acyl-phosphatidylethanolamines (NAPEs) to produce N-acylethanolamines (NAEs) and phosphatidic acid. Responsible for the generation of anandamide (N-arachidonoylethanolamine), the ligand of cannabinoid and vanilloid receptors (By similarity).
Gene Name:
NAPEPLD
Uniprot ID:
Q6IQ20
Molecular weight:
45595.15
General function:
Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes monounsaturated substrate anandamide preferentially as compared to polyunsaturated substrates.
Gene Name:
FAAH2
Uniprot ID:
Q6GMR7
Molecular weight:
58303.115
Reactions
Anandamide + Water → Arachidonic acid + Ethanolaminedetails
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding
Gene Name:
CNR1
Uniprot ID:
P21554
Molecular weight:
52857.4