Structure database (LMSD)

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LM IDLMGP06020030
Common NamePI(O-18:0/18:3(6Z,9Z,12Z))
Systematic Name1-octadecyl-2-(6Z,9Z,12Z-octadecatrienoyl)-glycero-3-phospho-(1'-myo-inositol)
SynonymsPI(O-36:3); PI(O-18:0/18:3)
Exact Mass
846.5622 (neutral)    Calculate m/z:
FormulaC45H83O12P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositols [GP06]
Sub Class1-alkyl,2-acylglycerophosphoinositols [GP0602]
AbbrevPI O-36:3
Abbrev ChainsPI O-18:0/18:3
PubChem CID52928444
SWISSLIPIDS IDSLM:000053443
InChIKeyZLULJPWGMXJGSF-DQLZCUBCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C45H83O12P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-54-36-38(37-55-58(52,53)57-45-43(50)41(48)40(47)42(49)44(45)51)56-39(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,24,26,38,40-45,47-51H,3-11,13,15-17,19,21-23,25,27-37H2,1-2H3,(H,52,53)/b14-12-,20-18-,26-24-/t38-,40-,41-,42+,43-,44-,45-/m1/s1
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SMILES
[C@]([H])(OC(CCCC/C=C\C/C=C\C/C=C\CCCCC)=O)(COP(=O)(O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O)COCCCCCCCCCCCCCCCCCC
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StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms58Rings1Aromatic Rings0Rotatable Bonds39
 van der Waals
Molecular Volume
889.45Topological Polar
Surface Area
192.44Hydrogen
Bond Donors
6Hydrogen
Bond Acceptors
12
 logP12.12Molar
Refractivity
235.11    
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.