Structure database (LMSD)

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LM IDLMGP06060002
Common NamePI(O-18:0/0:0)
Systematic Name1-octadecyl-glycero-3-phospho-(1'-myo-inositol)
SynonymsLPI(O-18:0)
Exact Mass
586.3482 (neutral)    Calculate m/z:
FormulaC27H55O11P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositols [GP06]
Sub ClassMonoalkylglycerophosphoinositols [GP0606]
PubChem CID52928629
SWISSLIPIDS IDSLM:000055176
InChIKeyBDLQBUDICUCZRI-RDGQAVELSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C27H55O11P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-36-19-21(28)20-37-39(34,35)38-27-25(32)23(30)22(29)24(31)26(27)33/h21-33H,2-20H2,1H3,(H,34,35)/t21-,22?,23-,24?,25?,26?,27-/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)COCCCCCCCCCCCCCCCCCC
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StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms39Rings1Aromatic Rings0Rotatable Bonds24
 van der Waals
Molecular Volume
579.82Topological Polar
Surface Area
186.37Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
11
 logP5.98Molar
Refractivity
151.97    
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.