Structure Database (LMSD)

Common Name
PI(18:2(9Z,12Z)/0:0)
Systematic Name
1-(9Z,12Z-octadecadienoyl)-glycero-3-phospho-(1'-myo-inositol)
Synonyms
  • LPI(18:2(9Z,12Z)/0:0)
  • LPI(18:2)
LM ID
LMGP06050010
Status
Active
Exact Mass
Calculate m/z
596.296168
Formula
Abbrev
Abbrev Chains
LPI 18:2




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MDLMOL SDF CSV TSV
MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

Main

Classification

String Representations

InChiKey (Click to copy)
SAHCQBPGXQFTRA-MUTGBQBKSA-N
InChi (Click to copy)
InChI=1S/C27H49O12P/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/h6-7,9-10,20,22-28,30-34H,2-5,8,11-19H2,1H3,(H,35,36)/b7-6-,10-9-/t20-,22-,23-,24+,25-,26-,27-/m1/s1
SMILES (Click to copy)
[C@]([H])(O)(COP(=O)(O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O)COC(CCCCCCC/C=C\C/C=C\CCCCC)=O

References

Reference
Improved method for the quantification of lysophospholipids
including enol ether species by liquid chromatography-tandem mass spectrometry
James G. Bollinger, Hiromi Ii, Martin Sadilek, and Michael H. Gelb
J. Lipid Res. 010 51:(2) 440-447

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Improved method for the quantification of lysophospholipids including enol ether species by liquid chromatography-tandem mass spectrometry.,
J Lipid Res, 2010
Pubmed ID: 19717841

Other Databases

PubChem CID
SwissLipids ID

Calculated Physicochemical Properties

Heavy Atoms 40
Rings 1
Aromatic Rings 0
Rotatable Bonds 22
Van der Waals Molecular Volume 580.69
Topological Polar Surface Area 203.44
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 12
logP 4.77
Molar Refractivity 151.43

Admin

Created at
-
Updated at
26th Jul 2021
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.