Structure Database (LMSD)

Common Name
PC(18:0/18:1(9Z))
Systematic Name
1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Synonyms
  • Choline phosphate, 3-ester with L-2-oleo-1-stearin
  • 1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine
  • L-alpha-1-Stearoyl-2-oleoyl lecithin
  • L-alpha-1-Stearoyl-2-oleoylphosphatidylcholine
  • SOPC
  • PC(18:0/18:1)
  • PC(36:1)
  • PC(18:0_18:1)
LM ID
LMGP01010761
Formula
C44H86NO8P
Exact Mass
Calculate m/z
787.609107
Sum Composition
PC 36:1
Abbrev Chains
PC 18:0_18:1
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Glycerophosphocholines [GP01]
Diacylglycerophosphocholines [GP0101]

Biological Context

1-Stearoyl-2-oleoyl-sn-glycero-3-PC is a phospholipid containing stearic acid and palmitic acid at the sn-1 and sn-2 positions, respectively.1 It has been used in the generation of lipid nanoparticles (LNPs) for the delivery of plasmid DNA in vitro.2 Liposomes containing 1-stearoyl-2-oleoyl-sn-glycero-3-PC and encapsulating the acetylcholinesterase (AChE) reactivator HI-6 (asoxime) increase the cerebral AChE reactivation rate by 10% compared with HI-6 alone in a mouse model of brain poisoning induced by the organophosphate nerve agent soman.3 It has also been found in whey protein phospholipid concentrate (WPPC).4

This information has been provided by Cayman Chemical

References

1. Tada, K., Goto, M., Tamai, N., et al. Pressure effect on the bilayer phase transition of asymmetric lipids with an unsaturated acyl chain. Ann. N. Y. Acad. Sci. 1189(1), 77-85 (2010).
2. Li, Z., Carter, J., Santos, L., et al. Acidification-induced structure evolution of lipid nanoparticles correlates with their in vitro gene transfections. ACS Nano 17(2), 979-990 (2023).
4. Ferraris, Q., Alcazar, A., and Qian, M.C. Profiling polar lipids in whey protein phospholipid concentrate by LC-HRMS/MS. Food Chem. 374, 131495 (2022).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
ATHVAWFAEPLPPQ-VRDBWYNSSA-N
InChi (Click to copy)
InChI=1S/C44H86NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,42H,6-20,22,24-41H2,1-5H3/b23-21-/t42-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O

Other Databases

LIPIDAT ID
174
HMDB ID
HMDB0008038
CHEBI ID
75034
PubChem CID
24778825
SwissLipids ID
SLM:000000671
Cayman ID
38152

Calculated Physicochemical Properties

Heavy Atoms 54
Rings 0
Aromatic Rings 0
Rotatable Bonds 43
Van der Waals Molecular Volume 862.99
Topological Polar Surface Area 111.19
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 9
logP 13.37
Molar Refractivity 224.72

Admin

Created at
-
Updated at
25th Apr 2022
LIPID MAPS® abbreviations for glycerophospholipids (GP)

The LIPID MAPS® glycerophospholipid abbreviations (PC, PE, etc.) are used here to refer to species with one or two radyl side-chains where the structures of the side chains are indicated within parentheses in the 'Headgroup(sn1/sn2)' format (e.g. PC(16:0/18:1(9Z)). By default, R stereochemistry at the C-2 carbon of glycerol and attachment of the headgroup at the sn3 position is assumed. Also, acyl chains are assumed by default. The 'O-' prefix is used to indicate the presence of an alkyl ether substituent e.g. PC(O-16:0/18:1(9Z)), whereas the 'P-' prefix is used for the 1Z-alkenyl ether (Plasmalogen) substituent e.g. PC(P-16:0/18:1(9Z)).

For molecules with opposite (S) stereochemistry at C2 of the glycerol group and attachment of the headgroup at the sn1 position, the stereochemistry specification of [S] is appended to the abbreviation. The 'Headgroup(sn3/sn2)' abbreviation format is used.

For molecules with unknown stereochemistry at the C-2 carbon of the glycerol group, the stereochemistry specification of [U] is appended to the abbreviation and the structure is drawn with C-2 stereochemistry unspecified.