N-(2-Hydroxyethyl)-7Z,10Z,13Z,16Z-docosatetraenamide
Basic information
- CAS
150314-35-5- Standard SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)NCCO- InChIKey
FMVHVRYFQIXOAF-DOFZRALJSA-N- Molecular formula
- C24H41NO2
- Average molar mass
- 375.6 g/mol
- Monoisotopic mass
- 375.31372955
Overview
7,10,13,16-Docosatetraenoylethanolamine is a N-acylethanolamine 22:4.
Names & identifiers
- Preferred name
- N-(2-Hydroxyethyl)-7Z,10Z,13Z,16Z-docosatetraenamide
- IUPAC
- (7Z,10Z,13Z,16Z)-N-(2-hydroxyethyl)docosa-7,10,13,16-tetraenamide
- English name
- DEA
- Molecular formula
- C24H41NO2
- Molecular weight
- 375.59
Names & synonyms
150314-35-57,10,13,16-Docosatetraenylethanolamide7,10,13,16-DTEADTXSID501028460N-(2-Hydroxyethyl)-7Z,10Z,13Z,16Z-docosatetraenamideRefChem:926699DTXCID901514033Adrenoyl-ethanolamine(7Z,10Z,13Z,16Z)-N-(2-hydroxyethyl)docosa-7,10,13,16-tetraenamideAdrenoyl-EA7,10,13,16-DocosatetraenoylethanolamineCHEMBL321585
Show more names
DOCOSATETRAENYLETHANOLAMIDEDOCOSATETRAENOYL ETHANOLAMIDE(all-Z)-N-(7,10,13,16-Docosatetraenoyl)ethanolamineAnandamide (22:4, n-6) (Docosatetraenylethanolamide)N-(2-HYDROXYETHYL)-7Z, 10Z, 13Z, 16Z-DOCOSATETRAENAMIDE7,10,13,16-Docosatetraenamide, N-(2-hydroxyethyl)-, (all-Z)-
N-docosatetra-7,10,13,16-enoylethanolamine(7Z,10Z,13Z,16Z)-N-(2-Hydroxyethyl)-7,10,13,16-docosatetraenamideANANDAMIDE (22:4,n-6)N-(7Z,10Z,13Z,16Z-docosatetraenoyl)-ethanolamineN-(2-Hydroxyethyl)-7,10,13,16-docosatetraenamide (all-Z)-7,10,13,16-Docosatetraenamide, N-(2-hydroxyethyl)-, (7Z,10Z,13Z,16Z)-Adrenoyl ethanolamideAnandamide + PMSF
Properties
Computed structural properties
- XLogP
- 6.4
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 18
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 436
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804]
Physical DescriptionSolid
Collision Cross Section202.37 Ų [M+H]+ [CCS Type: TIMS; Method: single field calibrated]
Physicochemical properties
- Boiling point
- 544.5 · 544.5±50.0 °C(Predicted)
- Density
- 0.932 · 0.932±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Desiccate at -20°C
- solubility
- 10 mg/ml; · DMF: 10 mg/ml; DMSO: 30 mg/ml; Ethanol: 100 mg/ml; Ethanol:PBS (1:2): 8 mg/ml; PBS (pH 7.2): <100 μg/ml
- pka
- 14.49 · 14.49±0.10(Predicted)
- Symbol(GHS)
- 2 · GHS02,GHS08
- Signal word
- Danger
- Hazard statements
- 225 · H225-H350
- Precautionary statements
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS08
- Hazard statements
- H225-H350
- Precautionary statements
- P201-P202-P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P308+P313-P370+P378-P403+P235-P405-P501
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
DescriptionDocosatetraenoyl ethanolamide (DEA) is an endocannabinoid containing docosatetraenoic acid in place of the arachidonate moiety of AEA. DEA acts on CB1 receptors with potency and efficacy similar to that of AEA. However, its specific role and relative importance as a cannabinergic neurotransmitter have not been elucidated.
Uses(7Z,10Z,13Z,16Z)-N-(2-Hydroxyethyl)-7,10,13,16-docosatetraenamide is an endocannabinoid and an analog of anandamide, which is an endogenous cannabinoid and TRPV1 receptor agonist.
Additional notes
DefinitionChEBI: 7,10,13,16-Docosatetraenoylethanolamine is a N-acylethanolamine 22:4.
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