Structure database (LMSD)

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LM IDLMGP20040004
Common NamePKDdiA-PS
Systematic Name1-hexadecanoyl-2-(9-oxo-11-carboxy-10E-undecenoyl)-sn-glycero-3-phosphoserine
Synonyms1-palmitoyl-2-(9-oxo-11-carboxy-10E-undecenoyl)-sn-glycero-3-phosphoserine
Exact Mass
721.3802 (neutral)    Calculate m/z:
FormulaC34H60NO13P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoserines [GP2004]
AbbrevPS 28:3;O3
PubChem CID134812385
InChIKeyDKZIWZNHQKKQPC-ZSUVMSPYSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C34H60NO13P/c1-2-3-4-5-6-7-8-9-10-11-12-15-18-21-32(39)45-25-29(26-46-49(43,44)47-27-30(35)34(41)42)48-33(40)22-19-16-13-14-17-20-28(36)23-24-31(37)38/h23-24,29-30H,2-22,25-27,35H2,1H3,(H,37,38)(H,41,42)(H,43,44)/b24-23+/t29-,30+/m1/s1
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SMILES
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(OC(CCCCCCCC(=O)/C=C/C(=O)O)=O)COC(CCCCCCCCCCCCCCC)=O)(=O)O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms49Rings0Aromatic Rings0Rotatable Bonds36
 van der Waals
Molecular Volume
726.02Topological Polar
Surface Area
226.05Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
14
 logP8.01Molar
Refractivity
184.95    
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.