Structure database (LMSD)

MDLMOL SDF CSV TSV MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM ID	LMGP03050013
Common Name	PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
Systematic Name	1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycero-3-phosphoserine
Synonyms	LPS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
Exact Mass	569.2754 (neutral)    Calculate m/z: (Select m/z)[M+H]+ [M+H-H2O]+ [M.]+ [M+2H]2+ [M+3H]3+ [M+4H]4+ [M+K]+ [M+2K]2+ [M+2K-H]+ [M+Na]+ [M+2Na]2+ [M+2Na-H]+ [M+Li]+ [M+2Li]2+ [M+NH4]+ [M-H]- [M-2H]2- [M-3H]3- [M-4H]4- [M+Cl]- [M+OAc]- M(neutral)
Formula	C28H44NO9P
Category	Glycerophospholipids [GP]
Main Class	Glycerophosphoserines [GP03]
Sub Class	Monoacylglycerophosphoserines [GP0305]
PubChem CID	52926281
SWISSLIPIDS ID	SLM:000030054
InChIKey	FZUFCKYWYUGORZ-SLSDLOGTSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI	InChI=1S/C28H44NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(31 )36-22-25(30)23-37-39(34,35)38-24-26(29)28(32)33/h3-4,6-7,9-10,12-13,15-16,18-19 ,25-26,30H,2,5,8,11,14,17,20-24,29H2,1H3,(H,32,33)(H,34,35)/b4-3-,7-6-,10-9-,13- 12-,16-15-,19-18-/t25-,26+/m1/s1
SMILES	C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(O)COC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\ CC)=O)(=O)O
MS Spectra	-      Predict MS/MS spectrum (Neg. mode)
Status	Active
References	Improved method for the quantification of lysophospholipids including enol ether species by liquid chromatography-tandem mass spectrometry James G. Bollinger, Hiromi Ii, Martin Sadilek, and Michael H. Gelb J. Lipid Res. 010 51:(2) 440-447
Calculated physicochemical properties (?):
Heavy Atoms 39 Rings 0 Aromatic Rings 0 Rotatable Bonds 24   van der Waals Molecular Volume 581.78 Topological Polar Surface Area 165.61 Hydrogen Bond Donors 4 Hydrogen Bond Acceptors 9   logP 6.51 Molar Refractivity 154.11
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.