Structure Database (LMSD)

Common Name
PC 18:1(9Z)/0:0
Systematic Name
1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Synonyms
  • Choline, phosphate 3-ester with 1-monoolein, L-
  • 1-O-Oleoyl-sn-glycero-3-phosphocholine
  • 1-Oleoyl-sn-glycero-3-phosphorylcholine
  • PC(18:1/0:0)
  • LPC(18:1)
LM ID
LMGP01050032
Formula
C26H52NO7P
Exact Mass
Calculate m/z
521.34814
Sum Composition
LPC 18:1
Abbrev Chains
LPC 18:1
Status
Curated
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Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Glycerophosphocholines [GP01]
Monoacylglycerophosphocholines [GP0105]

Biological Context

1-Oleoyl-2-hydroxy-sn-glycero-3-phosphocholine is a lysophospholipid containing oleic acid at the sn-1 position. It inhibits taurine uptake in Caco-2 cells when used at a concentration of 200 µM.1 Levels of 1-oleoyl-2-hydroxy-sn-glycero-3-phosphocholine are increased in conditioned medium in VEGF-stimulated primary normal human bronchial epithelial (NHBE) cells, an effect that can be reversed by the phospholipase A2 (PLA2) inhibitor oleyloxyethyl phosphorylcholine.2 Plasma levels of 1-oleoyl-2-hydroxy-sn-glycero-3-phosphocholine are decreased in patients with lung cancer or abdominal aortic aneurysm.3,4

This information has been provided by Cayman Chemical

References

1. Ishizuka, K., Miyamoto, Y., Satsu, H., et al. Characteristics of lysophosphatidylcholine in its inhibition of taurine uptake by human intestinal Caco-2 cells. Biosci. Biotechnol. Biochem. 66(4), 730-736 (2002).
2. Zhuge, Y., Yuan, Y., van Breemen, R., et al. Stimulated bronchial epithelial cells release bioactive lysophosphatidylcholine 16:0, 18:0, and 18:1. Allergy Asthma Immunol. Res. 6(1), 66-74 (2014).
3. Dong, J., Xiaoming, C., Zhao, L., et al. Lysophosphatidylcholine profiling of plasma: Discrimination of isomers and discovery of lung cancer biomarkers. Metabolomics 6(4), 478-488 (2010).
4. Xie, T., Lei, C., Song, W., et al. Plasma lipidomics analysis reveals the potential role of lysophosphatidylcholines in abdominal aortic aneurysm progression and formation. Int. J. Mol. Sci. 24(12), 10253 (2023).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
YAMUFBLWGFFICM-PTGWMXDISA-N
InChi (Click to copy)
InChI=1S/C26H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(O)COC(CCCCCCC/C=C\CCCCCCCC)=O

Other Databases

LIPIDAT ID
7279
HMDB ID
HMDB0002815
CHEBI ID
28610
PubChem CID
16081932
SwissLipids ID
SLM:000389824
Cayman ID
20959
GuidePharm ID
3623

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 0
Aromatic Rings 0
Rotatable Bonds 25
Van der Waals Molecular Volume 545.44
Topological Polar Surface Area 105.12
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 8
logP 6.56
Molar Refractivity 141.30

Admin

Created at
-
Updated at
11th Nov 2025
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.