Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20050017
Common NamePS-PI
Systematic Name1-hexadecanoyl-2-succinyl-sn-glycero-3-phospho-(1'-myo-inositol)
Synonyms1-palmitoyl-2-succinyl-sn-glycero-3-phospho-(1'-myo-inositol)
Exact Mass
672.3122 (neutral)    Calculate m/z:
FormulaC29H53O15P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoinositols [GP2005]
AbbrevPI 21:1;O
PubChem CID134812434
InChIKeyBOWZRUSZAGWCCQ-UKTNQKFDSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C29H53O15P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-22(32)41-18-20(43-23(33)17-16-21(30)31)19-42-45(39,40)44-29-27(37)25(35)24(34)26(36)28(29)38/h20,24-29,34-38H,2-19H2,1H3,(H,30,31)(H,39,40)/t20-,24-,25-,26+,27-,28-,29-/m1/s1
Click to highlight InChI
SMILES
CCCCCCCCCCCCCCCC(OC[C@](COP(O[C@@H]1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1O)O)O)O)O)(O)=O)(OC(=O)CCC(=O)O)[H])=O
Click to highlight SMILES
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms45Rings1Aromatic Rings0Rotatable Bonds27
 van der Waals
Molecular Volume
641.66Topological Polar
Surface Area
246.81Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
15
 logP4.85Molar
Refractivity
163.13    
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.