Anandamide (BioCAD00000006545)

blood cerebrospinal fluid (csf) urine plant natural products microbial natural products

Metabolite Card

Formula: C22H37NO2 (347.2824)
SMILES: CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

Synonyms [en]

anandamide; arachidonoyl ethanolamide; N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine; AEA; arachidonylethanolamide; (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Anandamide. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000006545). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Anandamide, 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).

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 94421-68-8
  • PubChem: 5281969
  • ChEBI: ChEBI:2700
  • HMDB: HMDB0004080
  • LipidMaps: LMFA08040001
  • KEGG: C11695
  • BioCyc: CPD-7598
  • NCBI MeSH: anandamide
  • Wikipedia: Anandamide
  • RefMet: RM0153077
  • MoNA: FiehnLib000698
  • MoNA: FiehnLib000699
  • MoNA: HMDB0004080_c_ms_99834
  • MoNA: HMDB0004080_c_ms_99835
  • MoNA: RP004101
  • MoNA: RP004102
  • MoNA: RP004103
  • Metlin: METLIN_3721
  • Coconut NaturalProduct: CNP0226272.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R09536 3.5.1.99 fatty acylamide amidohydrolase
BioCyc:RXN-20556 3.1.4.46 CPD-22238 + WATER --> CPD-7598 + GLYCEROL-3P + PROTON
Rhea:RHEA:26137 3.5.1.99 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O => ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
Rhea:RHEA:26138 3.5.1.99 ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate => N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O
Rhea:RHEA:26139 3.5.1.99 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O <=> ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
Rhea:RHEA:38752 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine => 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoate + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38753 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoate + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine => N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38754 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine <=> 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoate + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:45429 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O => N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + sn-glycerol 3-phosphate + H+
Rhea:RHEA:45430 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + sn-glycerol 3-phosphate + H+ => N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O
Rhea:RHEA:45431 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O <=> N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + sn-glycerol 3-phosphate + H+
Rhea:RHEA:45529 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O => N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H+
Rhea:RHEA:45530 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H+ => N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O
Rhea:RHEA:45531 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O <=> N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H+
Rhea:RHEA:45545 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O => N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H+
Rhea:RHEA:45546 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H+ => N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O
Rhea:RHEA:45547 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O <=> N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H+
Rhea:RHEA:53141 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + reduced [NADPH—hemoprotein reductase] + O2 => N-(8,9-epoxy-5Z,11Z,14Z-eicosatrienoyl)-ethanolamine + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:53142 N-(8,9-epoxy-5Z,11Z,14Z-eicosatrienoyl)-ethanolamine + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:53143 N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + reduced [NADPH—hemoprotein reductase] + O2 <=> N-(8,9-epoxy-5Z,11Z,14Z-eicosatrienoyl)-ethanolamine + oxidized [NADPH—hemoprotein reductase] + H2O + H+
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Organism Source

Taxonomy Source

  1. Acherontia atropus [ncbi taxid: ]
  2. Achillea macrophylla [ncbi taxid: 282746]
  3. Agave aurea [ncbi taxid: 467071]
  4. Ajuga spectabilis [ncbi taxid: 1586319]
  5. Alstroemeria revoluta [ncbi taxid: 198691]
  6. Astragalus tragacantha [ncbi taxid: 858344]
  7. Baphia nitida [ncbi taxid: 162666]
  8. Callistemon viminalis [ncbi taxid: 73737]
  9. Cissus pallidiflorus [ncbi taxid: ]
  10. Citrullus lanatus [ncbi taxid: 3654]
  11. Crataegus davisii [ncbi taxid: ]
  12. Crinum erubescens [ncbi taxid: 209093]
  13. Cupressus lawsoniana [ncbi taxid: ]
  14. Emilia sonchifolia [ncbi taxid: 415160]
  15. Encephalartos altensteinii [ncbi taxid: 3300]
  16. Eria foetida [ncbi taxid: ]
  17. Eupatorium havanense [ncbi taxid: ]
  18. Euphorbia kamerunica [ncbi taxid: ]
  19. Euphorbia marginata [ncbi taxid: 28955]
  20. Excoecaria oppositifolia [ncbi taxid: 3389821]
  21. Gardenia collinsae [ncbi taxid: 1233748]
  22. Grindelia acutifolia [ncbi taxid: ]
  23. Guanomyces polythrix [ncbi taxid: 110160]
  24. Gymnosporia senegalensis [ncbi taxid: 256095]
  25. Homo sapiens [ncbi taxid: 9606]
  26. Ircinia oros [ncbi taxid: 1141585]
  27. Jungermannia hyalina [ncbi taxid: ]
  28. Kobresia nepalensis [ncbi taxid: ]
  29. Ligularia muliensis [ncbi taxid: 2126609]
  30. Litsea aciculata [ncbi taxid: ]
  31. Litsea pulchella [ncbi taxid: ]
  32. Marrubium alysson [ncbi taxid: 694370]
  33. Melampodium heterophyllum [ncbi taxid: ]
  34. Myrmica sabuleti [ncbi taxid: 229917]
  35. Mytilus edulis [ncbi taxid: 6550]
  36. Nuphar lutea [ncbi taxid: 77113]
  37. Pausinystalia mayumbensis [ncbi taxid: ]
  38. Penicillium olsonii [ncbi taxid: 99116]
  39. Pentzia incana [ncbi taxid: 379275]
  40. Perilla frutescens var. arguta [ncbi taxid: 381201]
  41. Prangos pabularia [ncbi taxid: 52497]
  42. Pronephrium triphyllum [ncbi taxid: ]
  43. Selliguea feei [ncbi taxid: 194882]
  44. Shuteria involucrata var. vestita [ncbi taxid: 132463]
  45. Simaba multiflora [ncbi taxid: ]
  46. Sinocalamus affinis [ncbi taxid: ]
  47. Stevia chamaedrys [ncbi taxid: ]
  48. Teucrium oxylepis [ncbi taxid: 1209881]
  49. Trifolium subterraneum [ncbi taxid: 3900]
  50. Trillium camschatcense [ncbi taxid: 49675]
  51. Ursinia abrotanifolia [ncbi taxid: 3122733]
  52. Xenorhabdus bovienii [ncbi taxid: 40576]

Pathway Synthetic

pathway id name
BioCyc:SMAN_PWY6666-1 anandamide degradation
BioCyc:HUMAN_PWY6666-1 anandamide degradation
BioCyc:META_PWY6666-1 anandamide degradation
BioCyc:FLY_PWY6666-1 anandamide degradation
BioCyc:MOUSE_PWY6666-1 anandamide degradation
BioCyc:PCHR_PWY6666-1 anandamide degradation
Reactome:R-BTA-1430728 Metabolism
Reactome:R-BTA-556833 Metabolism of lipids
Reactome:R-CEL-2142753 Arachidonate metabolism
Reactome:R-CFA-1430728 Metabolism
Reactome:R-CFA-556833 Metabolism of lipids
Reactome:R-DRE-8978868 Fatty acid metabolism
Reactome:R-DME-2142753 Arachidonate metabolism
Reactome:R-GGA-8978868 Fatty acid metabolism
Reactome:R-MMU-1430728 Metabolism
Reactome:R-MMU-556833 Metabolism of lipids
Reactome:R-RNO-8978868 Fatty acid metabolism
Reactome:R-XTR-8978868 Fatty acid metabolism
Reactome:R-BTA-8978868 Fatty acid metabolism
Reactome:R-CEL-556833 Metabolism of lipids
View All Pathways