Compound
N-(9Z-octadecenoyl) ethanolamine
An N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide.
Definition from ChEBI (CHEBI:71466), read 2026-09-23. CC BY 4.0.
Structure
No three-dimensional record for this entry.
- Class
- Organic compound
- Formula
- C20H39NO2
- Mass
- 325.537 g/mol
- Charge
- 0
- InChIKey
- BOWVQLFMWHZBEF-KTKRTIGZSA-N
- SMILES
- CCCCCCCC/C=CCCCCCCCC(=O)NCCO
- Look it up
- ChEBIBy InChIKey
Identity from ChEBI. Not evidence.
What it touches on the way
Mechanistic reach
3 entities
3 entities reached.
What the reference databases state
Statements
4 statements
4 statements · 1 reference database · Subject: N-(9Z-octadecenoyl) ethanolamine · Sources: Rhea
- N-(9Z-octadecenoyl)-ethanolamine phosphate is converted to N-(9Z-octadecenoyl) ethanolamineCompoundRhea RHEA:62160Inferred only
- N-(9Z-octadecenoyl) ethanolamine is a substrate of FAAHProteinRhea RHEA:45060Inferred only
- N-(9Z-octadecenoyl) ethanolamine is a substrate of FAAH2ProteinRhea RHEA:45060Inferred only
- N-(9Z-octadecenoyl) ethanolamine is a substrate of PLA2G15ProteinRhea RHEA:38747Inferred only
Reactions
7 reactions
N-(9Z-octadecenoyl) ethanolamine+1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine2-[(9Z)-octadecenoylamino]ethyl (9Z)-octadecenoate+(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Catalysed by PLA2G15
Reaction pageLeft to rightBalanced
Rhea RHEA:38747CC BY 4.0Reference data
N-(9Z-octadecenoyl) ethanolamine+waterethanolamine+(9Z)-octadecenoate
Reaction pageLeft to rightBalanced
Rhea RHEA:45060CC BY 4.0Reference data
N-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+waterN-(9Z-octadecenoyl) ethanolamine+sn-glycerol 3-phosphate+hydron
Catalysed by GDE1
Reaction pageLeft to rightBalanced
Rhea RHEA:45432CC BY 4.0Reference data
N,1,2-tri-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+waterN-(9Z-octadecenoyl) ethanolamine+1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate+hydron
Catalysed by NAPEPLD
Reaction pageLeft to rightBalanced
Rhea RHEA:45532CC BY 4.0Reference data
1-O-(1Z-octadecenyl)-sn-glycero-3-phospho-(N-9Z-octadecenoyl)-ethanolamine+water1-O-(1Z-octadecenyl)-sn-glycero-3-phosphate+N-(9Z-octadecenoyl) ethanolamine+hydron
Reaction pageLeft to rightBalanced
Rhea RHEA:53188CC BY 4.0Reference data
N,1-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+waterN-(9Z-octadecenoyl) ethanolamine+1-(9Z-octadecenoyl)-sn-glycero-3-phosphate+hydron
Reaction pageLeft to rightBalanced
Rhea RHEA:56460CC BY 4.0Reference data
N-(9Z-octadecenoyl)-ethanolamine phosphate+waterN-(9Z-octadecenoyl) ethanolamine+hydrogenphosphate
Catalysed by PLPP1 or PLPP3 or PLPP2
Reaction pageLeft to rightBalanced
Rhea RHEA:62160CC BY 4.0Reference data
On the label
Labelled products
3 products
Source: NIH DSLD · Ingredient: N-(9Z-octadecenoyl) ethanolamine · 3 products · Declared amount per serving: 100–300 mg (2 products)
2 labels state an amount1 does not
- CymbiotikaMetabolic Health300 mgper 3 Vegetarian Capsule(s)DSLD:336114
- Morphogen NutritionMorpholean100 mgper 2 Capsule(s)DSLD:261254
- PerformixSSTOleoylethanolamide · Oleoylethanolamide powder (Form: std. to 15% Oleoylethanolamide)amount not statedper 8.3 Gram(s)DSLD:43371
Label record: NIH Office of Dietary Supplements · CC0
Other names
19 names
Resolves to: N-(9Z-octadecenoyl) ethanolamine
- Also called
- N-(2-Hydroxyethyl)-9-octadecenamideN-(2-Hydroxyethyl)oleamideN-(9Z-octadecenoyl)-ethanolamineN-(cis-9-octadecenoyl) ethanolamineN-(hydroxyethyl) oleamideN-(hydroxyethyl)oleamideN-oleoyl ethanolamineN-OleoylethanolamineNAE (18:1(9Z))NAE 18:1OEAOleamide MEAoleoyl 1-ethanolamideoleoyl ethanolamideOleoyl monoethanolamideOleoyl-EAoleoylethanolamideoleoylethanolamine
- Systematic name
- (9Z)-N-(2-hydroxyethyl)octadec-9-enamide