Structure database (LMSD)

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LM IDLMGP12010005
Common NameCL(1'-[22:1(13Z)/22:1(13Z)],3'-[22:1(13Z)/14:1(9Z)])[rac]
Systematic Name1'-[1,2-di-(13Z-docosenoyl)-sn-glycero-3-phospho],3'-[1-(13Z-docosenoyl),2-(9Z-
tetradecenoyl)-sn-glycero-3-phospho]-rac-glycerol
SynonymsCL(1'-[22:1/22:1],3'-[22:1/14:1])[rac]; CL(80:3); CL(14:1_22:1_22:1_22:1)
Exact Mass
1569.1600 (neutral)    Calculate m/z:
FormulaC89H166O17P2
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoglycerophosphoglycerols [GP12]
Sub ClassDiacylglycerophosphoglycerophosphodiradylglycerols [GP1201]
AbbrevCL 80:3
Abbrev ChainsCL 14:1_22:1_22:1_22:1
PubChem CID9547188
InChIKeyGFRCOIQJEYHQID-VIPLGEKESA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C89H166O17P2/c1-5-9-13-17-21-25-29-32-35-38-41-44-47-50-54-57-61-65-69-73-86(91)99-79-84(105-88(93)75-71-67-63-59-53-28-24-20-16-12-8-4)81-103-107(95,96)101-77-83(90)78-102-108(97,98)104-82-85(106-89(94)76-72-68-64-60-56-52-49-46-43-40-37-34-31-27-23-19-15-11-7-3)80-100-87(92)74-70-66-62-58-55-51-48-45-42-39-36-33-30-26-22-18-14-10-6-2/h20,24,32-37,83-85,90H,5-19,21-23,25-31,38-82H2,1-4H3,(H,95,96)(H,97,98)/b24-20-,35-32-,36-33-,37-34-/t83?,84-,85-/m1/s1
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SMILES
P(OC[C@]([H])(OC(CCCCCCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCCCCCC/C=C\CCCCCCCC)=O)(O)(OCC(O)([H])COP(OC[C@]([H])(OC(CCCCCCC/C=C\CCCC)=O)COC(CCCCCCCCCCC/C=C\CCCCCCCC)=O)(O)=O)=O
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MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms108Rings0Aromatic Rings0Rotatable Bonds90
 van der Waals
Molecular Volume
1716.23Topological Polar
Surface Area
236.95Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
17
 logP29.70Molar
Refractivity
450.09    
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.