Structure database (LMSD)

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LM IDLMGP10010024
Common NamePA(18:0/20:4(5Z,8Z,11Z,14Z))
Systematic Name1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate
Synonyms5,8,11,14-Eicosatetraenoic acid, 1-[[(1-oxooctadecyl)oxy]methyl]-2-
(phosphonooxy)ethyl ester, [R-(all-Z)]-; 1-Stearoyl-2-arachidonoyl-sn-glycero-
3-phosphate; PA(18:0/20:4); PA(38:4); PA(18:0_20:4)
Exact Mass
724.5043 (neutral)    Calculate m/z:
FormulaC41H73O8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub ClassDiacylglycerophosphates [GP1001]
LIPIDAT ID7253
PubChem CID5283529
HMDB IDHMDB0114884
CHEBI ID77239
SWISSLIPIDS IDSLM:000000872
InChIKeyAXJKOPKPNZMCIN-GSEBOFAUSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C41H73O8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(43)49-39(38-48-50(44,45)46)37-47-40(42)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,39H,3-10,12,14-16,18,20-21,23,25-27,29,31-38H2,1-2H3,(H2,44,45,46)/b13-11-,19-17-,24-22-,30-28-/t39-/m1/s1
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SMILES
[C@](COP(=O)(O)O)([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O
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MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms50Rings0Aromatic Rings0Rotatable Bonds38
 van der Waals
Molecular Volume
792.17Topological Polar
Surface Area
119.36Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP13.15Molar
Refractivity
208.00    
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.