Structure database (LMSD)

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LM IDLMGP03010039
Common NamePS(18:0/20:4(5Z,8Z,11Z,14Z))
Systematic Name1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine
SynonymsPS(18:0/20:4); PS(38:4); PS(18:0_20:4)
Exact Mass
811.5363 (neutral)    Calculate m/z:
FormulaC44H78NO10P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoserines [GP03]
Sub ClassDiacylglycerophosphoserines [GP0301]
PubChem CID24779545
HMDB IDHMDB0012383
SWISSLIPIDS IDSLM:000006154
InChIKeySVOUGFFDROZBJI-DNALCEECSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C44H78NO10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-43(47)55-40(38-53-56(50,51)54-39-41(45)44(48)49)37-52-42(46)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,40-41H,3-10,12,14-16,18,20-21,23,25-27,29,31-39,45H2,1-2H3,(H,48,49)(H,50,51)/b13-11-,19-17-,24-22-,30-28-/t40-,41+/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(CCCCCCCCCCCCCCCCC)=O)(=O)O
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MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms56Rings0Aromatic Rings0Rotatable Bonds42
 van der Waals
Molecular Volume
870.01Topological Polar
Surface Area
171.68Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
10
 logP12.99Molar
Refractivity
228.49    
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.