Structure Database (LMSD)

Common Name
PC(18:0/20:4(5Z,8Z,11Z,14Z))
Systematic Name
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
Synonyms
  • 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholine
  • PC(18:0/20:4)
  • Phosphatidylcholine(18:0/20:4w6)
  • 1-stearoyl-2-arachidonoyl-phosphatidylcholine
  • PC(38:4)
  • PC(18:0_20:4)
LM ID
LMGP01010802
Formula
C46H84NO8P
Exact Mass
Calculate m/z
809.593457
Sum Composition
PC 38:4
Abbrev Chains
PC 18:0_20:4
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
Predict MS/MS spectrum (Neg. Mode)

Classification

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

Biological Context

1-Stearoyl-2-arachidonoyl-sn-glycero-3-PC (SAPC) is a phospholipid containing stearic acid and arachidonic acid at the sn-1 and sn-2 positions, respectively. It is a component of LDL and has been found in human stenotic aortic valves and atherosclerotic plaques.1,2 Levels of SAPC are increased in the subepithelial invasive region compared to the superficial region of tumor tissue samples from patients with superficial-type pharyngeal squamous cell carcinoma.3 SAPC unilamellar vesicles have been used as substrates to quantify the activity of secretory phospholipase A2 (sPLA2) in the presence or absence of inhibitors.4 SAPC has also been used in the formation of lipid bilayers to study the effects of lipid composition on bilayer phase transitions.5

This information has been provided by Cayman Chemical

References

1. Milne, G.L., Seal, J.R., Havrilla, C.M., et al. Identification and analysis of products formed from phospholipids in the free radical oxidation of human low density lipoproteins. J. Lipid Res. 46(2), 307-319 (2005).
2. Lehti, S., Käkelä, R., Hörkkö, S., et al. Modified lipoprotein-derived lipid particles accumulate in human stenotic aortic valves. PLoS One 8(6), e65810 (2013).
3. Ishikawa, S., Tateya, I., Hayasaka, T., et al. The distribution of phosphatidylcholine species in superficial-type pharyngeal carcinoma. Biomed. Res. Int. 5387913, (2017).
4. Schebb, N.H., Falck, D., Faber, H., et al. Fast method for monitoring phospholipase A2 activity by liquid chromatography-electrospray ionization mass spectrometry. J. Chromatogr. A 1216(27), 5249-5255 (2009).
5. 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).

Reactions

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String Representations

InChiKey (Click to copy)
PSVRFUPOQYJOOZ-QNPWAGBNSA-N
InChi (Click to copy)
InChI=1S/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14,16,20,22,25,27,31,33,44H,6-13,15,17-19,21,23-24,26,28-30,32,34-43H2,1-5H3/b16-14-,22-20-,27-25-,33-31-/t44-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O

Other Databases

LIPIDAT ID
8641
HMDB ID
HMDB0008048
CHEBI ID
74965
PubChem CID
16219824
SwissLipids ID
SLM:000013549
Cayman ID
10009864

Calculated Physicochemical Properties

Heavy Atoms 56
Rings 0
Aromatic Rings 0
Rotatable Bonds 42
Van der Waals Molecular Volume 889.67
Topological Polar Surface Area 111.19
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 9
logP 13.48
Molar Refractivity 233.67

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.