1-Palmitoyl-2-oleoyl-sn-glycerol
Basic information
- CAS
29541-66-0- Standard SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)O[C@@H](CO)COC(=O)CCCCCCCCCCCCCCC- InChIKey
YEJYLHKQOBOSCP-OZKTZCCCSA-N- Molecular formula
- C37H70O5
- Average molar mass
- 594.9 g/mol
- Monoisotopic mass
- 594.52232533
Overview
1-palmitoyl-2-oleoyl-sn-glycerol is a 1,2-diacyl-sn-glycerol with palmitoyl as the 1-acyl group and oleoyl as the 2-acyl group. It has a role as a mouse metabolite. It is a 1,2-diacyl-sn-glycerol and a 1-palmitoyl-2-oleoylglycerol. It is an enantiomer of a 2-oleoyl-3-palmitoyl-sn-glycerol.
Names & identifiers
- Preferred name
- 1-Palmitoyl-2-oleoyl-sn-glycerol
- IUPAC
- [(2S)-1-hexadecanoyloxy-3-hydroxypropan-2-yl] (Z)-octadec-9-enoate
- English name
- 1-Palmitoyl-2-oleoyl-rac-glycerol
- Molecular formula
- C37H70O5
- Molecular weight
- 594.95
Names & synonyms
1-Palmitoyl-2-oleoyl-sn-glycerol[(2S)-1-hexadecanoyloxy-3-hydroxypropan-2-yl] (Z)-octadec-9-enoateCHEBI:75466(2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl (9Z)-octadec-9-enoate1-(14C)Pog2-(14C)Pog1-(1-14C)Palmitoyl-2-oleoyl-sn-glycerol1-Palmitoyl-2-(1-14C)oleoyl-sn-glycerol((2S)-1-hexadecanoyloxy-3-hydroxypropan-2-yl) (Z)-octadec-9-enoateRefChem:7685929541-66-016:0-18:1 DG
Show more names
POG1-Palmitoyl-2-oleoyl-rac-glycerol(2S)-2-O-Oleoyl-3-O-palmitoylglycerol(-)-1-O-Palmitoyl-2-O-oleoyl-L-glycerol9-Octadecenoic acid (9Z)-, (1S)-1-(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl ester
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol(S)-1-Hydroxy-3-(palmitoyloxy)propan-2-yl oleateFU2FI047ZIDG(16:0/18:1(9Z)/0:0)Olein, 1-palmito-2-, L-Palmitin, 2-oleo-1-, L-1-Palmitoyl-2-oleoylglycerol, (S)-DG 34:1
Database identifiers
Properties
Computed structural properties
- XLogP
- 14.2
- Topological polar surface area
- 72.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 35
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 603
Experimental & physicochemical properties
Lipids
Lipids -> Ambiguous Lipids
Lipids -> Glycerolipids [GL] -> Diradylglycerols [GL02] -> Diacylglycerols [GL0201]
Physical DescriptionSolid
Collision Cross Section261.0 Ų [M+NH4]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Ambiguous Lipids]
Physicochemical properties
- Boiling point
- 647.9 · 647.9±25.0 °C(Predicted)
- Density
- 0.932 · 0.932±0.06 g/cm3(Predicted)
- storage temp.
- -86 °C · -86°C Freezer
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Solid
- pka
- 13.69 · 13.69±0.10(Predicted)
- color
- Colourless to Off-White
- Stability
- -20 °C · Store at -20°C
- FDA UNII
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
- 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 PathwaysDe Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/14:1(9Z))
Applications
Uses1-Palmitoyl-2-oleoyl-sn-glycerol can be used in methods to enhance radiotherapy using ferroptosis inducers as radiosensitizers for identifying and treating a subject with a cancer that is resistant to radiotherapy.
Uses1-Palmitoyl-2-oleoyl-rac-glycerol is a monounsaturated diacylglycerol used to increase the activity of the ARF1 GTPase-activating protein on membrane-bound ARF1GTP.
Additional notes
DefinitionChEBI: 1-palmitoyl-2-oleoyl-sn-glycerol is a 1,2-diacyl-sn-glycerol with palmitoyl as the 1-acyl group and oleoyl as the 2-acyl group. It has a role as a mouse metabolite. It is a 1,2-diacyl-sn-glycerol and a 1-palmitoyl-2-oleoylglycerol. It is an enantiomer of a 2-oleoyl-3-palmitoyl-sn-glycerol.
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