Structure Database (LMSD)

Common Name
PKDdiA-PC
Systematic Name
1-hexadecanoyl-2-(9-oxo-11-carboxy-10E-undecenoyl)-sn-glycero-3-phosphocholine
Synonyms
  • 1-palmitoyl-2-(9-oxo-11-carboxy-10E-undecenoyl)-sn-glycero-3-phosphocholine
LM ID
LMGP20010017
Status
Active
Exact Mass
Calculate m/z
719.437352
Formula
Abbrev


Download as...
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)
XWKBYMQTSGGZLW-PHSKOSPPSA-N
InChi (Click to copy)
InChI=1S/C36H66NO11P/c1-5-6-7-8-9-10-11-12-13-14-15-18-21-24-35(41)45-30-33(31-47-49(43,44)46-29-28-37(2,3)4)48-36(42)25-22-19-16-17-20-23-32(38)26-27-34(39)40/h26-27,33H,5-25,28-31H2,1-4H3,(H-,39,40,43,44)/b27-26+/t33-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCC(=O)/C=C/C(=O)O)=O)COC(CCCCCCCCCCCCCCC)=O

References

Reference
Oxidized Phospholipids as Endogenous Pattern Recognition Ligands in Innate Immunity. Stanley L. Hazen. The Journal of Biological Chemistry. Volume 283, Issue 23, June 2008, pp. 15527-15531. DOI 10.1074/jbc.R700054200.

http://www.jbc.org/content/283/23/15527.full.pdf

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
Oxidized phospholipids as endogenous pattern recognition ligands in innate immunity.,
J Biol Chem, 2008
Pubmed ID: 18285328

Other Databases

PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 49
Rings 0
Aromatic Rings 0
Rotatable Bonds 36
Van der Waals Molecular Volume 745.68
Topological Polar Surface Area 165.56
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 12
logP 8.50
Molar Refractivity 190.13

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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.