Structure database (LMSD)

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LM IDLMGP04100001
Common NameLBPA(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
Systematic NameBis-[2-(5Z,8Z,11Z,14Z-eicosanoyl)-3-lyso-sn-glycero]-1-phosphate
SynonymsBis-[3-lyso-2-arachidonoyl-sn-glycerol]-1-phosphate; BMP(20:4(5Z,8Z,11Z,
14Z)/20:4(5Z,8Z,11Z,14Z)); LBPA(40:8); LBPA(20:4_20:4)
Exact Mass
818.5098 (neutral)    Calculate m/z:
FormulaC46H75O10P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoglycerols [GP04]
Sub ClassMonoacylglycerophosphomonoradylglycerols [GP0410]
AbbrevLBPA 40:8
Abbrev ChainsLBPA 20:4_20:4
PubChem CID56940666
SWISSLIPIDS IDSLM:000484681
InChIKeyNWJYJXGIDJPCOV-MOUZOFHSSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C46H75O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-45(49)55-43(39-47)41-53-57(51,52)54-42-44(40-48)56-46(50)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,43-44,47-48H,3-10,15-16,21-22,27-28,33-42H2,1-2H3,(H,51,52)/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-/t43-,44-/m0/s1
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SMILES
O(P(OC[C@](OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)([H])CO)(O)=O)C[C@@]([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)CO
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms57Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
885.69Topological Polar
Surface Area
148.82Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
10
 logP13.10Molar
Refractivity
235.32    
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.