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
Exact Mass
Calculate m/z
521.348142
Sum Composition
Abbrev Chains
LPC 18:1
Status
Curated
3D model of PC(18:1(9Z)/0:0)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
1-Oleoyl-2-hydroxy-sn-glycero-3-PC is an unsaturated 18:1 lysophosphatidylcholine formed in plasma by lecithin:cholesterol acyltransferase (LCAT).1,2 Lysophosphatidylcholines play a role in lipid signaling to regulate gene transcription, mitogenesis, monocyte chemotaxis, smooth muscle relaxation, and platelet activation.3,4,5
This information has been provided by Cayman Chemical
References
1. Lundbæk, J.A., and Andersen, O.S. Lysophospholipids modulate channel function by altering the mechanical properties of lipid bilayers. J. Gen. Physiol. 104(4), 645-673 (1994).
2. Yuan, Y., Schoenwaelder, S.M., Salem, H.H., et al. The bioactive phospholipid, lysophosphatidylcholine, induces cellular effects via G-protein-dependent activation of adenylyl cyclase. The Journal of Biological Chemisty 271(43), 27090-27098 (1996).
5. Soupene, E., Fyrst, H., and Kuypers, F.A. Mammalian acyl-CoA:lysophosphatidylcholine acyltransferase enzymes. Proc. Natl. Acad. Sci. USA 105(1), 88-93 (2008).
Reactions
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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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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
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
GuidePharm ID
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
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.
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.