Structure database (LMSD)

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LM IDLMGP10010026
Common NamePA(14:0/14:0)
Systematic Name1,2-ditetradecanoyl-sn-glycero-3-phosphate
SynonymsDimyristoyl phosphatidic acid; Tetradecanoic acid, 1-[(phosphonooxy)methyl]-1,
2-ethanediyl ester, (R)-; Myristin, 1,2-di-, dihydrogen phosphate, L-; 1,2-
Dimyristoyl-sn-glycero-3-phosphatidic acid; 1,2-Dimyristoyl-sn-glycero-3-
phosphatidic acid; Dimyristoyl-sn-glycerol 3-phosphate; L-alp; PA(28:0);
PA(14:0_14:0)
Exact Mass
592.4104 (neutral)    Calculate m/z:
FormulaC31H61O8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub ClassDiacylglycerophosphates [GP1001]
LIPIDAT ID8300
PubChem CID9547169
SWISSLIPIDS IDSLM:000025497
InChIKeyOZSITQMWYBNPMW-GDLZYMKVSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C31H61O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-30(32)37-27-29(28-38-40(34,35)36)39-31(33)26-24-22-20-18-16-14-12-10-8-6-4-2/h29H,3-28H2,1-2H3,(H2,34,35,36)/t29-/m1/s1
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SMILES
[C@](COP(=O)(O)O)([H])(OC(CCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCC)=O
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MS SpectraView MoNA MS spectra      Predict MS/MS spectrum (Neg. mode)
MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms40Rings0Aromatic Rings0Rotatable Bonds32
 van der Waals
Molecular Volume
629.73Topological Polar
Surface Area
119.36Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP10.15Molar
Refractivity
162.21    
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.