Structure Database (LMSD)
Common Name
PC(0:0/20:4;O2)
Systematic Name
2-(12S-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
Synonyms
- 12S-HpETE-LPC
- 12-HpETE-LPC
LM ID
LMGP20010056
Formula
Exact Mass
Calculate m/z
575.322322
Sum Composition
Abbrev Chains
LPC 0:0/20:4;O2
Status
Curated
3D model of PC(0:0/20:4;O2)
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)
AOZZZHHDWMLKEX-LLQMCKOFSA-N
InChi (Click to copy)
InChI=1S/C28H50NO9P/c1-5-6-7-8-13-16-19-26(38-32)20-17-14-11-9-10-12-15-18-21-28(31)37-27(24-30)25-36-39(33,34)35-23-22-29(2,3)4/h10-14,16-17,20,26-27,30H,5-9,15,18-19,21-25H2,1-4H3,(H-,32,33,34)/b12-10-,14-11-,16-13-,20-17+/t26-,27+/m0/s1
SMILES (Click to copy)
C(O[C@@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)CO)(CCC/C=C\C/C=C\C=C\[C@@H](OO)C/C=C\CCCCC)=O
Other Databases
PubChem CID
Calculated Physicochemical Properties
Heavy Atoms
39
Rings
0
Aromatic Rings
0
Rotatable Bonds
25
Van der Waals Molecular Volume
589.70
Topological Polar Surface Area
134.58
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
10
logP
6.59
Molar Refractivity
153.51
Admin
Created at
27th Aug 2020
Updated at
7th 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.