Structure Database (LMSD)

Common Name
PC(0:0/20:4;O)
Systematic Name
2-(12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
Synonyms
  • 12S-HETE-LPC
LM ID
LMGP20010055
Formula
Exact Mass
Calculate m/z
559.327407
Sum Composition
Abbrev Chains
LPC 0:0/20:4;O
Status
Curated

Classification

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
12-LOX catalyzes the oxidation of 2-arachidonoyl-lysolipids in platelets generating eicosanoid-lysolipids that are attenuated by iPLA2γ knockout.,
J Biol Chem, 2020
Pubmed ID: 32161117

String Representations

InChiKey (Click to copy)
GLFHTTFIWUDUDD-LLQMCKOFSA-N
InChi (Click to copy)
InChI=1S/C28H50NO8P/c1-5-6-7-8-13-16-19-26(31)20-17-14-11-9-10-12-15-18-21-28(32)37-27(24-30)25-36-38(33,34)35-23-22-29(2,3)4/h10-14,16-17,20,26-27,30-31H,5-9,15,18-19,21-25H2,1-4H3/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](O)C/C=C\CCCCC)=O

Other Databases

PubChem CID

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
27th 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.