Basic information
- CAS
179113-91-8- Standard SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O- InChIKey
YLEARPUNMCCKMP-DOFZRALJSA-N- Molecular formula
- C22H35NO3
- Average molar mass
- 361.5 g/mol
- Monoisotopic mass
- 361.26169398
Overview
N-arachidonoylglycine is biologically active derivative of anandamide. It is a N-acylglycine and a fatty amide. It is functionally related to an arachidonic acid. It is a conjugate acid of a N-arachidonoylglycinate.
Names & identifiers
- Preferred name
- N-Arachidonoyl glycine
- IUPAC
- 2-[[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]amino]acetic acid
- English name
- NAGLY
- Molecular formula
- C22H35NO3
- Molecular weight
- 361.52
Names & synonyms
N-arachidonoylglycine179113-91-8NAGlyN-arachidonoyl glycineDTXSID5045124N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycine2-[[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]amino]acetic acidDTXCID3025124CHEBI:589612-(((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl)amino)acetic acidRefChem:1091543N-arachidonylglycine
Show more names
NAGly, CID 5283389N-ARACHIDONYL GLYCINEN Arachidonylglycine,NArachidonylglycineN-Arachidonoyl glycine (solution in ethanol)N-(1-OXO-5Z,8Z,11Z,14Z-EICOSATETRAENYL)GLYCINE
arachidonoyl glycineNA-Glyarachidonyl glycine5PB56SQA6EUNII-5PB56SQA6ECHEMBL161343NCGC00015042-032-((5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenamido)acetic acid
Database identifiers
- CAS
179113-91-8- PubChem CID
- 5283389
- DTXSID
Properties
Computed structural properties
- XLogP
- 5.6
- Topological polar surface area
- 66.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 16
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 476
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl amino acids [FA0805]
LogP4.043
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 560.9 · 560.9±50.0 °C(Predicted)
- Density
- 0.985 · 0.985±0.06 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 5 mg/mL, · DMSO: >5 mg/mL, soluble
- form
- waxy solid
- pka
- 3.58 · 3.58±0.10(Predicted)
- color
- off-white
- Sensitive
- Air Sensitive
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Product is subject to oxidation. Solutions in degassed DMSO may be stored at -20°C for up to 1 month.
- InChIKey
- YLEARPUNMCCKMP-DOFZRALJSA-N
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
- Warning
- Symbol(GHS)
- GHS07,GHS08
- safety_code
- 22-24/25
- target organs
- Central nervous system
- Hazard statements
- H315-H319-H336-H351
- Hazard Classifications
- Carc. 2Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P201-P302+P352-P305+P351+P338-P308+P313
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
DescriptionArachidonoyl glycine (N-arachidonyl glycine; NAGly) has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA; anandamide), from extracts of mammalian brain, and has also been synthesized as an analog of AEA for structure/activity testing. NAGly may be produced endogenously via oxidation of AEA, or by transacylation of arachidonoyl CoA. NAGly is reported to have analgesic activities in whole animal experiments. Since it seems to be a very poor ligand for the CB1 receptor, these effects are probably mediated via other signaling pathways.
UsesArachidonoyl glycine (N-arachidonyl glycine; NAGly) has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA; anandamide), from extracts of mammalian brain, and has also been synthesized as an analog of AEA for structure/activity testing. NAGly may be produced endogenously via oxidation of AEA, or by transacylation of arachidonoyl CoA. NAGly is reported to have analgesic activities in whole animal experiments. Since it seems to be a very poor ligand for the CB1 receptor, these effects are probably mediated via other signaling pathways.[Cayman Chemical]
UsesAn endogenous anandamide-like compound; also acts as a T-type Ca2+ channel blocker and an endogenous GLYT2 inhibitor.
Suppliers34 total
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
Related reactions
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Compound notes
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