Structure database (LMSD)

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LM IDLMGP01012205
Common NamePC(20:3(5Z,8Z,11Z)/22:1(13Z))
Systematic Name1-(5Z,8Z,11Z-eicosatrienoyl)-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholine
SynonymsPC(42:4); PC(20:3_22:1)
Exact Mass
865.6561 (neutral)    Calculate m/z:
FormulaC50H92NO8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphocholines [GP01]
Sub ClassDiacylglycerophosphocholines [GP0101]
AbbrevPC 42:4
Abbrev ChainsPC 20:3_22:1
PubChem CID53478985
HMDB IDHMDB0008382
YMDB IDYMDB02100
CHEBI ID89196
InChIKeyQLUBHBLHAFOGNI-FLBVHRRTSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C50H92NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h20-23,28,30,34,36,48H,6-19,24-27,29,31-33,35,37-47H2,1-5H3/b22-20-,23-21-,30-28-,36-34-/t48-/m1/s1
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SMILES
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCCCCC/C=C\CCCCCCCC)=O)COC(CCC/C=C\C/C=C\C/C=C\CCCCCCCC)=O
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StatusActive
CommentsYeast Metabolome Database (http://www.ymdb.ca)
Calculated physicochemical properties (?):
 Heavy Atoms60Rings0Aromatic Rings0Rotatable Bonds46
 van der Waals
Molecular Volume
958.87Topological Polar
Surface Area
111.19Hydrogen
Bond Donors
0Hydrogen
Bond Acceptors
9
 logP15.04Molar
Refractivity
252.14    
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.