Structure database (LMSD)

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LM IDLMGP06050006
Common NamePI(20:4(5Z,8Z,11Z,14Z)/0:0)
Systematic Name1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1'-myo-inositol)
SynonymsPI(20:4/0:0); LPI(20:4/0:0); 20:4 Lyso-PI; 1-arachidonoyl-
phosphatidylinositol; LPI(20:4)
Exact Mass
620.2962 (neutral)    Calculate m/z:
FormulaC29H49O12P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositols [GP06]
Sub ClassMonoacylglycerophosphoinositols [GP0605]
PubChem CID42607497
InChIKeyLXUGKKVCSTYZFK-MUOQEERCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C29H49O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(31)39-20-22(30)21-40-42(37,38)41-29-27(35)25(33)24(32)26(34)28(29)36/h6-7,9-10,12-13,15-16,22,24-30,32-36H,2-5,8,11,14,17-21H2,1H3,(H,37,38)/b7-6-,10-9-,13-12-,16-15-/t22-,24?,25-,26?,27?,28?,29-/m1/s1
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SMILES
[C@]([H])(O)(COP(=O)(O)O[C@@H]1C(O)[C@H](O)C(O)C(O)C1O)COC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms42Rings1Aromatic Rings0Rotatable Bonds22
 van der Waals
Molecular Volume
610.01Topological Polar
Surface Area
203.44Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
12
 logP5.10Molar
Refractivity
160.48    
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.