Metabolite Card
Formula: C20H41NO2 (327.3137)
SMILES: CCCCCCCCCCCCCCCCCC(=O)NCCO
Synonyms [en]
Stearoyl ethanolamide; stearoylethanolamide; N-(2-Hydroxyethyl)octadecanamide; Stearoyl-EA; Monoethanolamine stearic acid amide; N-stearoylethanolamine
Last reviewed on 2024-06-28.
Cite this Page
Stearoylethanolamide. 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: BioCAD00000025556). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Stearoylethanolamide is an N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337, 12056855, 12560208, 11997249).
DBLinks
- CAS Registry Number: 111-57-9
- PubChem CID: 27902
- ChEBI: 85299
- HMDB: HMDB0013078
- LipidMaps: LMFA08040051
- KEGG:
- BioCyc: CPD-20400
- NCBI MeSH: stearoylethanolamide
- Wikipedia: Stearoylethanolamide
Other DBLinks
- CAS Registry Number: 111-57-9
- CAS Registry Number: 8038-89-9
- PubChem: 27902
- ChEBI: ChEBI:85299
- HMDB: HMDB0013078
- HMDB: HMDB13078
- LipidMaps: LMFA08040051
- BioCyc: CPD-20400
- NCBI MeSH: stearoylethanolamide
- Wikipedia: Stearoylethanolamide
- RefMet: RM0153067
- MoNA: CCMSLIB00004684206
- MoNA: CCMSLIB00004684225
- MoNA: LipidBlast2022_063645
- Metlin: METLIN_3720
- Coconut NaturalProduct: CNP0346699.0
Class / Ontology
- WishartLab ClassyFire: [Amines] Amines
- RefMet: [NAE] NAE
- LipidMaps: [N-acyl ethanolamines (endocannabinoids) [FA0804]] N-acyl ethanolamines (endocannabinoids) [FA0804]
- ChEBI: [CHEBI:85299] N-(octadecanoyl)ethanolamine
- Coconut NaturalProduct: [N-acyl ethanolamines (endocannabinoids)] N-acyl ethanolamines (endocannabinoids)
| ID | EC Number | Name |
|---|---|---|
| Rhea:RHEA:45537 | N-octadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O => N-octadecanoyl ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H+ | |
| Rhea:RHEA:45538 | N-octadecanoyl ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H+ => N-octadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O | |
| Rhea:RHEA:45539 | N-octadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O <=> N-octadecanoyl ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H+ | |
| Rhea:RHEA:63125 | N-octadecanoyl ethanolamine + H2O => octadecanoate + ethanolamine | |
| Rhea:RHEA:63126 | octadecanoate + ethanolamine => N-octadecanoyl ethanolamine + H2O | |
| Rhea:RHEA:63127 | N-octadecanoyl ethanolamine + H2O <=> octadecanoate + ethanolamine | |
| BioCyc:RXN-20508 | 3.5.1.60 | CPD-20400 + WATER --> STEARIC_ACID + ETHANOL-AMINE |
| BioCyc:RXN-20515 | 3.1.4.54 | N-stearoyl-PE + WATER --> CPD-20400 + L-PHOSPHATIDATE + PROTON |