Structure database (LMSD)

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LM IDLMGP03010038
Common NamePS(16:0/20:4(5Z,8Z,11Z,14Z))
Systematic Name1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine
SynonymsPS(16:0/20:4); PS(36:4); PS(16:0_20:4)
Exact Mass
783.5050 (neutral)    Calculate m/z:
FormulaC42H74NO10P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoserines [GP03]
Sub ClassDiacylglycerophosphoserines [GP0301]
PubChem CID24779544
HMDB IDHMDB0012361
CHEBI ID90029
SWISSLIPIDS IDSLM:000005941
InChIKeyDKLQKRSJZISZKW-KNFJROLASA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C42H74NO10P/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-41(45)53-38(36-51-54(48,49)52-37-39(43)42(46)47)35-50-40(44)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13,17-18,20,22,26,28,38-39H,3-10,12,14-16,19,21,23-25,27,29-37,43H2,1-2H3,(H,46,47)(H,48,49)/b13-11-,18-17-,22-20-,28-26-/t38-,39+/m1/s1
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SMILES
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCC)=O)(=O)O
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MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms54Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
835.41Topological Polar
Surface Area
171.68Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
10
 logP12.21Molar
Refractivity
219.25    
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.