Basic information
- CAS
109001-03-8- Standard SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO- InChIKey
OVKKNJPJQKTXIT-JLNKQSITSA-N- Molecular formula
- C22H35NO2
- Average molar mass
- 345.5 g/mol
- Monoisotopic mass
- 345.26677936
Overview
(5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine is an N-acylethanolamine 20:5 that is the ethanolamide of (5Z,8Z,11Z,14Z17Z)-eicosapentaenoic acid. It has a role as a PPARgamma agonist. It is a N-acylethanolamine 20:5 and an endocannabinoid. It is functionally related to an all-cis-5,8,11,14,17-icosapentaenoic acid.
Names & identifiers
- Preferred name
- (5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine
- IUPAC
- (5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide
- English name
- Eicosapentaenoyl Ethanolamide
- Molecular formula
- C22H35NO2
- Molecular weight
- 345.52
Names & synonyms
CHEBI:71467N-cis-5,8, 11,14,17-eicosapentaenoylethanolamine(5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamineRefChem:1050641Eicosapentaenoyl Ethanolamide109001-03-8EPEA(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamideAnandamide (20:5, n-3)CHEMBL3358297NAE 20:5N-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-ethanolamine
Show more names
Eicosapentaenoyl Ethanolamide(solution in ethanol)5(Z),8(Z),11(Z),14(Z),17(Z)-Eicosapentaenoyl EthanolamideN-(2-hydroxyethyl)-5(Z),8(Z),11(Z),14(Z),17(Z)-eicosapentaenamide5,8,11,14,17-Eicosapentaenamide, N-(2-hydroxyethyl)-, (5Z,8Z,11Z,14Z,17Z)-
(5Z,8Z,11Z,14Z,17Z)-N-(2-Hydroxyethyl)-5,8,11,14,17-eicosapentaenamideN-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z,17Z-eicosapentaenamideLMFA08040008icosapentaenoyl ethanolamideH4VNL4V73XSCHEMBL1228841OVKKNJPJQKTXIT-JLNKQSITSA-NDTXSID901153302
Database identifiers
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 15
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 445
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804]
Physical DescriptionSolid
Collision Cross Section186.44 Ų [M+H]+ [CCS Type: TIMS; Method: single field calibrated]
Physicochemical properties
- Boiling point
- 522.5 · 522.5±50.0 °C(Predicted)
- Density
- 0.951 · 0.951±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
- pka
- 14.48 · 14.48±0.10(Predicted)
- form
- oil
- color
- colorless to yellow
- InChIKey
- OVKKNJPJQKTXIT-JLNKQSITSA-N
- SMILES
- CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO
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
- wgk
- 3
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H225-H319
- Precautionary statements
- P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
UsesEicosapentaenoyl Ethanolamide inhibits dietary-restriction-induced lifespan extension in wild type and TOR pathway mutant nematodes.
Suppliers13 total
陕西缔都新材料有限公司81124267 17392282731 · [email protected]
宜昌众意泰贸易有限公司0717-6449896 13886658719 · [email protected]
Nantong HI-FUTURE Biology Co., Ltd.+86-18051384581 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
韶关市启程生物科技有限公司18122215013 · [email protected]
Alfa Chemistry1-516-6625404 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
天津凯利奇生物科技有限公司15076683720 · [email protected]
南通全益生物科技有限公司+86-0513; 18051384581 · [email protected]
上海宏叶生物科技有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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