Structure database (LMSD)

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

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

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.