Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP08010004
Common NamePIP2[4',5'](8:0/8:0)
Systematic Name1,2-(dioctanoyl)-sn-glycero-3-phospho-(1'- myo-inositol-4',5'-bisphosphate)
Synonyms1,2-dioctanoyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)
Exact Mass
746.2081 (neutral)    Calculate m/z:
FormulaC25H49O19P3
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositol bisphosphates [GP08]
Sub ClassDiacylglycerophosphoinositol bisphosphates [GP0801]
AbbrevPIP2 16:0
Abbrev ChainsPIP2 8:0_8:0
PubChem CID136212534
CHEBI ID84241
InChIKeyXLNCEHRXXWQMPK-PSHUMLBPSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C25H49O19P3/c1-3-5-7-9-11-13-18(26)39-15-17(41-19(27)14-12-10-8-6-4-2)16-40-47(37,38)44-23-20(28)21(29)24(42-45(31,32)33)25(22(23)30)43-46(34,35)36/h17,20-25,28-30H,3-16H2,1-2H3,(H,37,38)(H2,31,32,33)(H2,34,35,36)/t17-,20?,21+,22?,23-,24?,25?/m1/s1
Click to highlight InChI
SMILES
[C@]([H])(OC(CCCCCCC)=O)(COP(=O)(O)O[C@@H]1C(O)[C@H](O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1O)COC(CCCCCCC)=O
Click to highlight SMILES
StatusActive
ReferencesDetection of Endogenous Phosphatidylinositol 4,5–bisphosphate in Phytophthora cinnamomi. Jeff M. Howard, Peter L. Beech and Damien L. Callahan. Volume 53, Issue 8, August 2018, pp. 835-839. https://doi.org/10.1002/lipd.12093.

https://aocs.onlinelibrary.wiley.com/doi/full/10.1002/lipd.12093
Calculated physicochemical properties (?):
 Heavy Atoms47Rings1Aromatic Rings0Rotatable Bonds26
 van der Waals
Molecular Volume
649.92Topological Polar
Surface Area
302.57Hydrogen
Bond Donors
8Hydrogen
Bond Acceptors
19
 logP5.14Molar
Refractivity
163.97    
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.