Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP12020001
Common NameCL(1'-[18:2(9Z,12Z)/18:2(9Z,12Z)],3'-[18:2(9Z,12Z)/0:0])
Systematic Name1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1-(9Z,12Z-
octadecadienoyl)-sn-glycero-3-phospho]-sn-glycerol
SynonymsMLCL(1'-[18:2(9Z,12Z)/18:2(9Z,12Z)],3'-[18:2(9Z,12Z)/0:0]); CL(54:6);
CL(0:0_18:2_18:2_18:2)
Exact Mass
1186.7426 (neutral)    Calculate m/z:
FormulaC63H112O16P2
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoglycerophosphoglycerols [GP12]
Sub ClassDiacylglycerophosphoglycerophosphomonoradylglycerols [GP1202]
PubChem CID52929773
SWISSLIPIDS IDSLM:000389882
InChIKeyXGVZPSSAPUZKKQ-VKBUHLKPSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C63H112O16P2/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-61(66)73-
52-58(64)53-75-80(69,70)76-54-59(65)55-77-81(71,72)78-57-60(79-63(68)51-48-45-42
-39-36-33-30-27-24-21-18-15-12-9-6-3)56-74-62(67)50-47-44-41-38-35-32-29-26-23-2
0-17-14-11-8-5-2/h16-21,25-30,58-60,64-65H,4-15,22-24,31-57H2,1-3H3,(H,69,70)(H,
71,72)/b19-16-,20-17-,21-18-,28-25-,29-26-,30-27-/t58-,59+,60-/m1/s1
SMILESP(OC[C@]([H])(OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)COC(CCCCCCC/C=C\C/C=C\CCCCC)=O)(O)(O
C[C@](O)([H])COP(OC[C@]([H])(O)COC(=O)CCCCCCC/C=C\C/C=C\CCCCC)(O)=O)=O
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms81Rings0Aromatic Rings0Rotatable Bonds62
 van der Waals
Molecular Volume
1255.00Topological Polar
Surface Area
230.88Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
16
 logP19.32Molar
Refractivity
329.55    
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.