Structure Database (LMSD)
Common Name
PC(0:0/20:4;O)
Systematic Name
2-(15S-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
Synonyms
- 15S-HETE-LPC
LM ID
LMGP20010054
Formula
Exact Mass
Calculate m/z
559.327407
Sum Composition
Abbrev Chains
LPC 0:0/20:4;O
Status
Active
3D model of PC(0:0/20:4;O)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
References
String Representations
InChiKey (Click to copy)
UGWAFZVUHJCWOQ-SUJBQGSKSA-N
InChi (Click to copy)
InChI=1S/C28H50NO8P/c1-5-6-16-19-26(31)20-17-14-12-10-8-7-9-11-13-15-18-21-28(32)37-27(24-30)25-36-38(33,34)35-23-22-29(2,3)4/h7-8,11-14,17,20,26-27,30-31H,5-6,9-10,15-16,18-19,21-25H2,1-4H3/b8-7-,13-11-,14-12-,20-17+/t26-,27+/m0/s1
SMILES (Click to copy)
C(OP(OCC[N+](C)(C)C)([O-])=O)[C@]([H])(OC(=O)CCC/C=C\C/C=C\C/C=C\C=C\[C@@H](O)CCCCC)CO
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
38
Rings
0
Aromatic Rings
0
Rotatable Bonds
24
Van der Waals Molecular Volume
580.91
Topological Polar Surface Area
125.35
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
9
logP
5.93
Molar Refractivity
152.15
Admin
Created at
20th Aug 2020
Updated at
8th Nov 2024
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.