Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP00000064
Common NamemLPA(O-16:0)
Systematic Name1-O-hexadecyl-sn-glycero-3-phosphoric acid methyl ester
Synonyms-
Exact Mass
410.2797 (neutral)    Calculate m/z:
FormulaC20H43O6P
CategoryGlycerophospholipids [GP]
Main ClassOther Glycerophospholipids [GP00]
Sub Class-
PubChem CID137323909
InChIKeyIXJRAZBOBFNYIJ-HXUWFJFHSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C20H43O6P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-25-18-20(21)19-26-27(22,23)24-2/h20-21H,3-19H2,1-2H3,(H,22,23)/t20-/m1/s1
Click to highlight InChI
SMILES
[C@](COP(=O)(O)OC)([H])(O)COCCCCCCCCCCCCCCCC
Click to highlight SMILES
StatusActive
ReferencesA novel self-lipid antigen targets human T cells against CD1c(+) leukemias.
Lepore M, de Lalla C, Gundimeda SR, Gsellinger H, Consonni M, Garavaglia C, Sansano S, Piccolo F, Scelfo A, Haussinger D, Montagna D, Locatelli F, Bonini C, Bondanza A, Forcina A, Li Z, Ni G, Ciceri F, Jeno P, Xia C, Mori L, Dellabona P, Casorati G, De Libero G.
J Exp Med. 2014 Jun 30;211(7):1363-77. doi: 10.1084/jem.20140410.

http://jem.rupress.org/content/211/7/1363.long
Calculated physicochemical properties (?):
 Heavy Atoms27Rings0Aromatic Rings0Rotatable Bonds21
 van der Waals
Molecular Volume
427.13Topological Polar
Surface Area
85.22Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
6
 logP6.92Molar
Refractivity
111.77    
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.