Oleamide (BioCAD00000015524)

plant natural products

Metabolite Card

Chinese Name: 油酰胺
Formula: C18H35NO (281.2719)
SMILES: 

CCCCCCCC\C=C/CCCCCCCC(N)=O

Synonyms [en]

oleamide; Oleyl amide; oleic acid amide; (Z)-9-OCTADECENAMIDE; 9Z-octadecenamide; oleylamide

Reviewed

Last reviewed on 2026-04-16.

Cite this Page

Oleamide. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/Oleamide (retrieved 2026-08-20) (CAD Registry RN: BioCAD00000015524). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Oleamide is an amide of the fatty acid oleic acid. It is an endogenous substance: it occurs naturally in the body of animals. It accumulates in the cerebrospinal fluid during sleep deprivation and induces sleep in animals. It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression. The mechanism of action of oleamide's sleep inducing effects is an area of current research. It is likely that oleamide interacts with multiple neurotransmitter systems. Oleamide is structurally related to the endogenous cannabinoid anandamide, and has the ability to bind to the CB1 receptor as a full agonist.

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 181057-55-6
  • CAS Registry Number: 301-02-0
  • CAS Registry Number: 3322-62-1
  • PubChem: 1930
  • PubChem: 5283387
  • ChEBI: ChEBI:116314
  • HMDB: HMDB0002117
  • LipidMaps: LMFA08010004
  • KEGG: C19670
  • BioCyc: CPD6666-1
  • NCBI MeSH: oleylamide
  • Wikipedia: Oleamide
  • RefMet: RM0150636
  • MoNA: CCMSLIB00004684211
  • MoNA: HMDB0002117_c_ms_102656
  • MoNA: HMDB0002117_c_ms_99751
  • MoNA: HMDB0002117_c_ms_99752
  • MoNA: JP003588
  • MoNA: JP008351
  • Metlin: METLIN_4115
  • Coconut NaturalProduct: CNP0300480.0
  • PMHub: MS000002279
  • metaboanalyst: 2eb0292e5b4ff2f431c359efda4434ce
  • metaboanalyst: 5b2abe84aedff39bc3586710e0e7a6ed
  • metaboanalyst: 7ab7fd2bb9b59fb8904f13bf201b4246
  • metaboanalyst: a81a35e3bdf66bfba31535dc077b156e
  • HERB: HBIN024967

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R09537 3.5.1.99 fatty acylamide amidohydrolase
Rhea:RHEA:26507 3.5.1.99 (9Z)-octadecenamide + H2O => (9Z)-octadecenoate + NH4+
Rhea:RHEA:26508 3.5.1.99 (9Z)-octadecenoate + NH4+ => (9Z)-octadecenamide + H2O
Rhea:RHEA:26509 3.5.1.99 (9Z)-octadecenamide + H2O <=> (9Z)-octadecenoate + NH4+
Rhea:RHEA:58637 N-(9Z-octadecenoyl)-(2S)-hydroxyglycine => (9Z)-octadecenamide + glyoxylate
Rhea:RHEA:58638 (9Z)-octadecenamide + glyoxylate => N-(9Z-octadecenoyl)-(2S)-hydroxyglycine
Rhea:RHEA:58639 N-(9Z-octadecenoyl)-(2S)-hydroxyglycine <=> (9Z)-octadecenamide + glyoxylate
BioCyc:RXN-10756 3.5.1.99 CPD6666-1 + WATER --> OLEATE-CPD + AMMONIUM
Rhea:RHEA:26506 [26506] (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
Rhea:RHEA:58636 [58636] N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
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Mass Spectrum
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View All Mass Spectrum
Organism Source

Taxonomy Source

  1. Angelica acutiloba [ncbi taxid: 55605]
  2. Angelica gigas [ncbi taxid: 85712]
  3. Angelica sinensis [ncbi taxid: 165353]
  4. Bryophyllum pinnatum [ncbi taxid: ]
  5. Calotropis gigantea [ncbi taxid: 4066]
  6. Centella asiatica [ncbi taxid: 48106]
  7. Citrullus lanatus [ncbi taxid: 3654]
  8. Crinum asiaticum [ncbi taxid: 205937]
  9. Crinum asiaticum var. sinicum [ncbi taxid: 223245]
  10. Eucalyptus microtheca [ncbi taxid: 183840]
  11. Homo sapiens [ncbi taxid: 9606]
  12. Spirodela polyrhiza [ncbi taxid: 29656]
  13. Streptomyces blastmyceticus strain 12-6 [ncbi taxid: ]
  14. Streptomyces rochei [ncbi taxid: 1928]
  15. Streptomyces sundarbansensis [ncbi taxid: 265730]
  16. Zingiber officinale [ncbi taxid: 94328]

Pathway Synthetic

pathway id name
PlantCyc:SPIRODELA_PWY-6483 ceramide degradation (generic)
PlantCyc:VCARTERI_PWY-6483 ceramide degradation
PlantCyc:ZMARINA_LIPASYN-PWY phospholipases
PlantCyc:CGIGANTEA_PWY-6483 ceramide degradation (generic)
PlantCyc:CGIGANTEA_LIPASYN-PWY phospholipases
PlantCyc:CZOFINGIENSIS_LIPASYN-PWY phospholipases
PlantCyc:CSUBELLIPSOIDEA_LIPASYN-PWY phospholipases
PlantCyc:WATERMELON_PWY-6483 ceramide degradation (generic)
PlantCyc:WATERMELON_PWY-6803 phosphatidylcholine acyl editing
PlantCyc:PAPAYA_PWY-2501 fatty acid α-oxidation I (plants)
PlantCyc:PAPAYA_LIPASYN-PWY phospholipases
PlantCyc:PAPAYA_PWY-6483 ceramide degradation (generic)
PlantCyc:PINEAPPLE_PWY-6803 phosphatidylcholine acyl editing
PlantCyc:PINEAPPLE_LIPASYN-PWY phospholipases
PlantCyc:PINEAPPLE_PWY-6483 ceramide degradation (generic)
PlantCyc:BLACKPEPPER_LIPASYN-PWY phospholipases
PlantCyc:BLACKPEPPER_PWY-6483 ceramide degradation (generic)
PlantCyc:VCARTERI_LIPASYN-PWY phospholipases
PlantCyc:ZMARINA_PWY-2501 fatty acid α-oxidation I (plants)
PlantCyc:ZMARINA_PWY-6803 phosphatidylcholine acyl editing
View All Pathways