Basic information
- CAS
4004-05-1- Standard SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)OC(=O)CCCCCCC/C=C\CCCCCCCC- InChIKey
MWRBNPKJOOWZPW-NYVOMTAGSA-N- Molecular formula
- C41H78NO8P
- Average molar mass
- 744 g/mol
- Monoisotopic mass
- 743.54650509
Overview
1,2-di-[(9Z)-octadecenoyl]-sn-glycero-3-phosphoethanolamine is a 1,2-diacyl-sn-glycero-3-phosphoethanolamine in which the acyl substituent both at positions 1 and 2 is specified as (9Z)-octadecenoyl respectively. It has a role as a mouse metabolite. It is functionally related to an oleic acid.
Names & identifiers
- Preferred name
- 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine
- IUPAC
- [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate
- English name
- 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine
- Molecular formula
- C41H78NO8P
- Molecular weight
- 744.05
Names & synonyms
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine4004-05-1DOPE, l-PE(18:1(9Z)/18:1(9Z))JNP6V6AI0UDOPE, R-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineDTXSID601029609RefChem:9067451-2-DOPEDTXCID9017759541-2-di-(9-octadecenoyl)-sn-glycero-3-phosphoethethanolamine
Show more names
1,2-Di(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine1,2-Dioleoyl-sn-glycero-3-PEDIOLEOYL PHOSPHATIDYL ETHANOLAMINE(Z)-(2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate18:1 PEDOPE (18:1 PE)DOPE, 10 mM in DMSOCOATSOME ME-8181 (DOPE)
(2-aminoethoxy)((2R)-2,3-bis((9Z)-octadec-9-enoyloxy)propoxy)phosphinic acidDOPEDOPE (Excipient)PE(18:1/18:1)1,2-Dioleoyl-sn-glGPEtn(18:1w9/18:1w9)SCHEMBL25038GPEtn(18:1/18:1)
Database identifiers
Properties
Computed structural properties
- XLogP
- 10.6
- Topological polar surface area
- 134 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 41
- Heavy atoms
- 51
- Formal charge
- 0
- Complexity
- 897
Experimental & physicochemical properties
Lipids
Lipids -> Unambiguous Lipids
Lipids -> Glycerophospholipids [GP] -> Glycerophosphoethanolamines [GP02] -> Diacylglycerophosphoethanolamines [GP0201]
Physical DescriptionSolid
Collision Cross Section
270.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
278.8 Ų [M+H]+
Physicochemical properties
- Melting point
- 200 °C · 200°C(lit.)
- Boiling point
- 759.2 · 759.2±70.0 °C(Predicted)
- Density
- 1.008 · 1.008±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 31.25 mg/mL · DMSO: 31.25 mg/mL (42.00 mM)
- pka
- 1.17 · 1.17±0.50(Predicted)
- form
- lyophilized powder
- color
Safety & regulation
Safety data
- F
- 8-10-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- ridadr
- UN 1888 6.1/PG 3
- hs_code
- 29232000
- risk_code
- 22-38-40-48/20/22-67-36/38-20-63
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- Xn
- safety_code
- 36/37-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H331-H336-H351-H361d-H372-H412
- 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(18:1(9Z)/18:1(9Z))
Applications
Description1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) is a neutral phospholipid and displays sensitivity towards pH change and has been used in the preparation of liposome and giant unilamellar vesicles (GUVs).Phosphatidylethanolamine (PE) is formed primarily in the reaction of CDP-ethanolamine and diacylglycerol. PE is one of the major components of cell membranes in bacteria and in nervous system.
Uses1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) forms heterogenous liposomes with N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium methylsulfate (DOTAP), which are used as delivery vehicles for therapeutic agents.
Uses1,2-Dioleoyl-sn-glycero-3-phosphatidylethanolamine (DOPE) is a synthetic analog of naturally-occurring PE containing 18:1 fatty acids at the sn-1 and sn-2 positions. DOPE can be used as an emulsifier to facilitate DNA-liposome complex transport across membranes. It is used in combination with cationic phospholipids to increase efficiency during DNA transfection studies as a non-viral method of gene delivery.
Uses18:1 (Δ9-Cis) PE (DOPE) has been used in the preparation of liposome for human uncoupling protein 1 (UCP1) reconstitution and for Caenorhabditis elegans autophagy related cysteine protease protein conjugation studies. It has also been used for the generation of giant unilamellar vesicles (GUVs) for septin induced deformation studies.
General Description1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (18:1 (Δ9-Cis) PE (DOPE)) is a neutral phospholipid and displays sensitivity towards pH change. At acidic it is an inverted hexagonal micelle and transforms to spherical micelle at alkaline pH.
Upstream & downstream products
Related reactions
3 records
Compound notes
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