Basic information
- CAS
185435-28-3- Standard SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)OCC(O)CO- InChIKey
PAZGBAOHGQRCBP-DDDNOICHSA-N- Molecular formula
- C40H77O10P
- Average molar mass
- 749 g/mol
- Monoisotopic mass
- 748.52543565
Overview
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol is a phosphatidylglycerol in which the 1- and 2-acyl groups are specified as palmitoyl and oleoyl respectively. It is functionally related to a hexadecanoic acid and an oleic acid. It is a conjugate acid of a 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol(1-).
Names & identifiers
- Preferred name
- 1-Palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol))
- IUPAC
- [(2R)-1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (Z)-octadec-9-enoate
Names & synonyms
185435-28-31-Palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol1-Palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol))POPG, l-POPG, R-F72017VPR7L-alpha-1-Palmitoyl-2-oleoylglycerophosphoglycerol9-Octadecenoic acid (9Z)-, (1R)-1-((((2,3-dihydroxypropoxy)hydroxyphosphinyl)oxy)methyl)-2-((1-oxohexadecyl)oxy)ethyl ester9-Octadecenoic acid (Z)-, 1-((((2,3-dihydroxypropoxy)hydroxyphosphinyl)oxy)methyl)-2-((1-oxohexadecyl)oxy)ethyl ester, (1R)-(2,3-dihydroxypropoxy)[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid(2,3-dihydroxypropoxy)((2R)-3-(hexadecanoyloxy)-2-((9Z)-octadec-9-enoyloxy)propoxy)phosphinic acidRefChem:76856
Show more names
POPG[(2R)-1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (Z)-octadec-9-enoate1-Palmitoyl-2-oleoyl-sn-glycero-3-phospho-rac-glycerol1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-rac-glycerol)1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol16:0-18:1 PGUNII-F72017VPR7PG(16:0/18:1)
Properties
Computed structural properties
- XLogP
- 12.3
- Topological polar surface area
- 149 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 41
- Heavy atoms
- 51
- Formal charge
- 0
- Complexity
- 868
Experimental & physicochemical properties
LipidsLipids -> Glycerophospholipids [GP] -> Glycerophosphoglycerols [GP04] -> Diacylglycerophosphoglycerols [GP0401]
Chemistry & industry
Pharmacology
PharmacodynamicsPalmitoyloleoyl-phosphatidylglycerol is a replacement surfactant which prevents alveolar collapse when administered intratracheally.
Mechanism of ActionPalmitoyloleoyl-phosphatidylglycerol reduces interfacial tension at the air/water interfaces in the alveoli. This prevents the tension from pulling the alveolar membranes inwards which would collapse them and lead to respiratory distress.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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