Structure Database (LMSD)

Common Name
PC(0:0/20:4;O)
Systematic Name
2-(15R-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
Synonyms
  • 15R-HETE-LPC
LM ID
LMGP20010053
Status
Active
Exact Mass
Calculate m/z
559.327407
Formula
Abbrev
Abbrev Chains
LPC 0:0/20:4;O


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MDLMOL SDF CSV TSV
MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

Main

Classification

String Representations

InChiKey (Click to copy)
UGWAFZVUHJCWOQ-FWJSUUQISA-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-/m1/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

References

Reference
Cyclooxygenase-2 Mediated Oxidation of 2-Arachidonoyl-Lysophospholipids Identifies Unknown Lipid Signaling Pathways
Cell Chem. Biol. 2016
DOI: 10.1016/j.chembiol.2016.08.009
PMID: 27642067

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Cyclooxygenase-2 Mediated Oxidation of 2-Arachidonoyl-Lysophospholipids Identifies Unknown Lipid Signaling Pathways.,
Cell Chem Biol, 2016
Pubmed ID: 27642067

Other Databases

CHEBI ID
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
20th Aug 2020
Updated at
20th Aug 2020
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.