1,2-Didocosahexaenoyl-sn-glycero-3-phosphoethanolamine
Basic information
- CAS
123284-81-1- Standard SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)OC[C@H](COP(=O)(O)OCCN)OC(=O)CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC- InChIKey
RBDNSJMXMWTPCS-NYUVKXDYSA-N- Molecular formula
- C49H74NO8P
- Average molar mass
- 836.1 g/mol
- Monoisotopic mass
- 835.51520532
Overview
1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine is a 1,2-diacyl-sn-glycero-3-phosphoethanolamine in which both the acyl groups specified is (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl. It has a role as a mouse metabolite. It is functionally related to an all-cis-docosa-4,7,10,13,16,19-hexaenoic acid.
Names & identifiers
- Preferred name
- 1,2-Didocosahexaenoyl-sn-glycero-3-phosphoethanolamine
- IUPAC
- [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]oxypropyl] (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
- English name
- 1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine
- Molecular formula
- C49H74NO8P
- Molecular weight
- 836.09
Names & synonyms
123284-81-11,2-Docosahexanoyl-sn-glycero-3-phosphoethanolamine146IH66H584,7,10,13,16,19-Docosahexaenoic acid, 1,1'-((1R)-1-((((2-aminoethoxy)hydroxyphosphinyl)oxy)methyl)-1,2-ethanediyl) ester, (4Z,4'Z,7Z,7'Z,10Z,10'Z,13Z,13'Z,16Z,16'Z,19Z,19'Z)-DTXSID1012113881,2-didocosahexaenoyl-sn-glycero-3-phosphoethanolamine4,7,10,13,16,19-Docosahexaenoic acid, 1,1'-[(1R)-1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl] ester, (4Z,4'Z,7Z,7'Z,10Z,10'Z,13Z,13'Z,16Z,16'Z,19Z,19'Z)-RefChem:934971DTXCID801642750PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))UNII-146IH66H58PE(22:6/22:6)
Show more names
GPEtn(22:6/22:6)GPEtn(22:6n3/22:6n3)GPEtn(22:6w3/22:6w3)1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolaminePhophatidylethanolamine(22:6/22:6)[(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]oxypropyl] (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoatePE(22:6n3/22:6n3)PE(22:6w3/22:6w3)
Properties
Computed structural properties
- XLogP
- 8.4
- Topological polar surface area
- 134 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 39
- Heavy atoms
- 59
- Formal charge
- 0
- Complexity
- 1,460
Experimental & physicochemical properties
LipidsLipids -> Glycerophospholipids [GP] -> Glycerophosphoethanolamines [GP02] -> Diacylglycerophosphoethanolamines [GP0201]
Physical DescriptionSolid
Collision Cross Section
283.9 Ų [M-H]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]
299.7 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
276.99 Ų [M-H]- [CCS Type: TIMS; Method: single field calibrated]
Physicochemical properties
- Boiling point
- 824.5 · 824.5±75.0 °C(Predicted)
- Density
- 1.037 · 1.037±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- pka
- 1.17 · 1.17±0.50(Predicted)
- form
- liquid
- InChIKey
- RBDNSJMXMWTPCS-NYUVKXDYSA-N
- SMILES
- [H][C@@](COP([O-])(OCC[NH3+])=O)(OC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O)COC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O
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
- WGK 3
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- Storage Class
- 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
- target organs
- Central nervous system, Liver,Kidney
- Hazard statements
- H302-H315-H319-H331-H336-H351-H361d-H372-H412
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Chronic 3Carc. 2Eye Irrit. 2Repr. 2Skin Irrit. 2STOT RE 1STOT SE 3
- Precautionary statements
- P201-P273-P301+P312+P330-P302+P352-P304+P340+P311-P308+P313
Chemistry & industry
Pharmacology
Tissue LocationsAll Tissues
Cellular LocationsExtracellular
Metabolite PathwaysPhosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
Applications
Uses22:6 PE has been used as a standard for the optimization of liquid chromatography-mass spectrometry (LC/MS) conditions and to detect the serum antiphosphatidylethanolamine (aPE) antibodies from patients using enzyme linked immunosorbent assay (ELISA). It is suitable for use in testing the effect of increasing acyl chain unsaturation on phase separation from the lipid raft molecules spingomyelin (SM) and cholesterol (CHOL).
General Description22:6 PE is a polyunsaturated homoacid. Phosphatidylethanolamine (PE) is a membrane phospholipid. The types of PE depends on the combination of free fatty acids on the α and β position. 22:6 PE denotes the length of the carbon chain:degree of unsaturation in the PE.
Additional notes
DefinitionChEBI: 1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine is a 1,2-diacyl-sn-glycero-3-phosphoethanolamine in which both the acyl groups specified is (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl. It has a role as a mouse metabolite. It is functionally related to an all-cis-docosa-4,7,10,13,16,19-hexaenoic acid.
Related reactions
0 records
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Compound notes
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