Structure database (LMSD)

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LM IDLMGP02060007
Common Name6-O-(1-O-stearoyl-sn-glycero-3-phosphono)-1D-myo-inositol
Systematic Name(2R)-2-hydroxy-3-[(hydroxy{[(1S,2R,3S,4S,5S,6S)-2,3,4,5,6-
pentahydroxycyclohexyl]oxy}phosphoryl)oxy]propyl octadecanoate
Synonyms(2R)-2-hydroxy-3-[(hydroxy{[(1S,2R,3S,4S,5S,6S)-2,3,4,5,6-
pentahydroxycyclohexyl]oxy}phosphoryl)oxy]propyl stearate;6-O-(1-O-
octadecanoyl-sn-glycero-3-phosphono)-1D-myo-
inositol;lysophosphatidylmyoinositol
Exact Mass
600.3275 (neutral)    Calculate m/z:
FormulaC27H53O12P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassMonoalkylglycerophosphoethanolamines [GP0206]
PubChem CID46878550
CHEBI ID59994
InChIKeyMXAFDFDAIFZFET-JAKHPNLRSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C27H53O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(29)37-18-20(28)19-38-40(35,36)39-27-25(33)23(31)22(30)24(32)26(27)34/h20,22-28,30-34H,2-19H2,1H3,(H,35,36)/t20-,22-,23+,24+,25+,26-,27-/m1/s1
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SMILES
O=P(O[C@H]1[C@H](O)[C@@H](O)[C@@H]([C@H](O)[C@@H]1O)O)(OC[C@H](O)COC(=O)CCCCCCCCCCCCCCCCC)O
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MS SpectraView MoNA MS spectra     
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms40Rings1Aromatic Rings0Rotatable Bonds24
 van der Waals
Molecular Volume
585.97Topological Polar
Surface Area
203.44Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
12
 logP5.22Molar
Refractivity
151.62    
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.