(8Z,11Z,14Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamide
Basic information
- CAS
150314-34-4- Standard SMILES
CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)NCCO- InChIKey
ULQWKETUACYZLI-QNEBEIHSSA-N- Molecular formula
- C22H39NO2
- Average molar mass
- 349.5 g/mol
- Monoisotopic mass
- 349.29807949
Overview
(Z,Z,Z)-icosa-8,11,14-trienoylethanolamide is a N-acylethanolamine 20:3.
Names & identifiers
- Preferred name
- (8Z,11Z,14Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamide
- IUPAC
- (8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide
- English name
- Dihomo-gamma-linolenylethanolamide
- Molecular formula
- C22H39NO2
- Molecular weight
- 349.55
Names & synonyms
HGLEA150314-34-4Homo-gamma-linolenylethanolamideAnandamide (20.3,n-6)Homo-gamma-linolenoyl ethanolamideDTXSID201199860(8Z,11Z,14Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamideRefChem:906311DTXCID801631068(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide8,11,14-EicosatrienoylethanolamideN-homo-gamma-linolenoylethanolamine
Show more names
Dihomo-γ-linolenylethanolamideDihomo-γ-linolenylethanolamideDihomo-γ-Linolenoyl EthanolamideDihomo-γ-Linolenoyl EthanolamideDihomo-gamma-linolenylethanolamideDIHOMO-GAMMA-LINOLENOYL ETHANOLAMIDE
N-(8Z,11Z,14Z-icosatrienoyl)-ethanolamideN-(8Z,11Z,14Z-eicosatrienoyl)-ethanolamineDihomo-gamma-linolenoyl-EACHEMBL121229(Z,Z,Z)-icosa-8,11,14-trienoylethanolamideANANDAMIDE (20:3,n-6)dihomo-gamma-linolenoylethanol amide(Z,Z,Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamide
Database identifiers
- CAS
150314-34-4
Properties
Computed structural properties
- XLogP
- 6
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 17
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 372
Experimental & physicochemical properties
Lipids
Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804]
Physical DescriptionSolid
Collision Cross Section196.4 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]
Physicochemical properties
- Boiling point
- 522.1 · 522.1±50.0 °C(Predicted)
- Density
- 0.929 · 0.929±0.06 g/cm3(Predicted)
- 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)
- FDA UNII
- 5 G69TJKH · UR5G69TJKH
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
Uses(8Z,11Z,14Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamide is an endocannabinoid that binds to recombinant human CB1 and CB2 receptors. (8Z,11Z,14Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamide is a CB1 and CB2 agonist and an adenylyl cyclase inhibitor.
Additional notes
DefinitionChEBI: (Z,Z,Z)-icosa-8,11,14-trienoylethanolamide is a N-acylethanolamine 20:3.
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