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    Popg, L-

    PharmaCompass
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    2D Structure
    Also known as: Popg, Popg, l-, Popg, r-, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol, 185435-28-3, F72017vpr7
    Molecular Formula
    C40H77O10P
    Molecular Weight
    749.0  g/mol
    InChI Key
    PAZGBAOHGQRCBP-DDDNOICHSA-N
    FDA UNII
    F72017VPR7
    Palmitoyloleoyl-phosphatidylglycerol was a component of Surfaxin, discontinued in 2017, which acted as a surfactant. The product was meant to compensate for alveolar surfactant deficiency and reduce to likelihood of alveolar collapse leading to acute respiratory collapse.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2R)-1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (Z)-octadec-9-enoate
    2.1.2 InChI
    InChI=1S/C40H77O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,37-38,41-42H,3-16,19-36H2,1-2H3,(H,45,46)/b18-17-/t37?,38-/m1/s1
    2.1.3 InChI Key
    PAZGBAOHGQRCBP-DDDNOICHSA-N
    2.1.4 Canonical SMILES
    CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO)O)OC(=O)CCCCCCCC=CCCCCCCCC
    2.1.5 Isomeric SMILES
    CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCC(CO)O)OC(=O)CCCCCCC/C=C\CCCCCCCC
    2.2 Other Identifiers
    2.2.1 UNII
    F72017VPR7
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Popg

    2. Popg, L-

    3. Popg, R-

    4. 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol

    5. 185435-28-3

    6. F72017vpr7

    7. L-alpha-1-palmitoyl-2-oleoylglycerophosphoglycerol

    8. 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol

    9. 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-rac-glycerol

    10. 1-hexadecanoyl-2-(9z-octadecenoyl)-sn-glycero-3-phospho-(1'-rac-glycerol)

    11. [(2r)-1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (z)-octadec-9-enoate

    12. 9-octadecenoic Acid (9z)-, (1r)-1-((((2,3-dihydroxypropoxy)hydroxyphosphinyl)oxy)methyl)-2-((1-oxohexadecyl)oxy)ethyl Ester

    13. 9-octadecenoic Acid (z)-, 1-((((2,3-dihydroxypropoxy)hydroxyphosphinyl)oxy)methyl)-2-((1-oxohexadecyl)oxy)ethyl Ester, (1r)-

    14. Pg(16:0/18:1)

    15. 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-rac-glycerol Sodium Salt

    16. Unii-f72017vpr7

    17. 1-hexadecanoyl-2-(9z-octadecenoyl)-sn-glycero-3-phospho-sn-glycerol

    18. Chebi:34080

    19. Palmitoyloleoyl-phosphatidylglycerol

    20. Lmgp04010002

    21. 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1'-rac-glycerol)

    22. Db11331

    23. 1-palmitoyl-2-oleoyl-phosphatidylglycerol

    24. Hy-142991

    25. Cs-0374728

    26. 16:0-18:1 Pg

    27. 490h053

    28. Q27115796

    29. L-.alpha.-1-palmitoyl-2-oleoylglycerophosphoglycerol

    30. 1-o-(1-o-palmitoyl-2-o-oleoyl-l-glycero-3-phospho)glycerol

    31. {1-hexadecanoyl-2-[(z)-octadec-9-enoyl]-sn-glycero-3-phospho}glycerol

    32. (19r)-22,25,26-trihydroxy-16,22-dioxo-17,21,23-trioxa-22lambda(5)-phosphahexacosan-19-yl (9z)-octadec-9-enoate

    33. 1-hexadecanoyl-2-[cis-9-octadecanoyl]-sn-glycero-3-[phospho-rac-(1-glycerol)] Ammonium Salt

    34. 9-octadecenoic Acid (9z)-, 1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-2-[(1-oxohexadecyl)oxy]ethyl Ester

    2.4 Create Date
    2006-01-13
    3 Chemical and Physical Properties
    Molecular Weight 749.0 g/mol
    Molecular Formula C40H77O10P
    XLogP312.3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count41
    Exact Mass748.52543565 g/mol
    Monoisotopic Mass748.52543565 g/mol
    Topological Polar Surface Area149 Ų
    Heavy Atom Count51
    Formal Charge0
    Complexity868
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Palmitoyloleoyl-phosphatidylglycerol was a component of Surfaxin which was indicated for the prevention of respiratory distress syndrome in premature infants.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Palmitoyloleoyl-phosphatidylglycerol is a replacement surfactant which prevents alveolar collapse when administered intratracheally.

    5.2 Mechanism of Action

    Palmitoyloleoyl-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.