Structure database (LMSD)

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LM IDLMGP03020009
Common NamePS(O-16:0/17:2(9Z,12Z))
Systematic Name1-hexadecyl-2-(9Z,12Z-heptadecadienoyl)-glycero-3-phosphoserine
SynonymsPS(O-33:2); PS(O-16:0/17:2)
Exact Mass
731.5101 (neutral)    Calculate m/z:
FormulaC39H74NO9P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoserines [GP03]
Sub Class1-alkyl,2-acylglycerophosphoserines [GP0302]
AbbrevPS O-33:2
Abbrev ChainsPS O-16:0/17:2
PubChem CID52926098
InChIKeyPYBKSJHXTIWVGG-CBIJSSGGSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C39H74NO9P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-38(41)49-36(34-47-50(44,45)48-35-37(40)39(42)43)33-46-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h9,11,15,17,36-37H,3-8,10,12-14,16,18-35,40H2,1-2H3,(H,42,43)(H,44,45)/b11-9-,17-15-/t36-,37+/m1/s1
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SMILES
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(OC(CCCCCCC/C=C\C/C=C\CCCC)=O)COCCCCCCCCCCCCCCCC)(=O)O
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StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms50Rings0Aromatic Rings0Rotatable Bonds39
 van der Waals
Molecular Volume
782.64Topological Polar
Surface Area
154.61Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
9
 logP12.25Molar
Refractivity
205.94    
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.