Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP15010050
Common NamePIM2(16:0/14:0)
Systematic Name2'-O-(α-D-Manp)-6'-O-(α-D-Manp)-(1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-
phospho-1'-myo-inositol)
SynonymsPIM2(30:0); PIM2(14:0_16:0)
Exact Mass
1106.6002 (neutral)    Calculate m/z:
FormulaC51H95O23P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositolglycans [GP15]
Sub ClassDiacylglycerophosphoinositolglycans [GP1501]
PubChem CID126457418
InChIKeyJWXUMTZFOCCKNP-HFFOTSMUSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C51H95O23P/c1-3-5-7-9-11-13-15-16-18-19-21-23-25-27-36(54)67-31-33(69-3
7(55)28-26-24-22-20-17-14-12-10-8-6-4-2)32-68-75(65,66)74-49-47(72-50-45(63)40(5
8)38(56)34(29-52)70-50)43(61)42(60)44(62)48(49)73-51-46(64)41(59)39(57)35(30-53)
71-51/h33-35,38-53,56-64H,3-32H2,1-2H3,(H,65,66)/t33-,34?,35?,38-,39+,40?,41?,42
+,43?,44?,45-,46+,47-,48?,49+,50-,51+/m1/s1
SMILES[C@](COP(O[C@@H]1C(O[C@H]2[C@H](C(O)[C@@H](O)C(CO)O2)O)C(O)[C@@H](O)C(O)[C@H]1O[
C@@H]1[C@@H](C(O)[C@H](O)C(CO)O1)O)(=O)O)([H])(OC(CCCCCCCCCCCCC)=O)COC(CCCCCCCCC
CCCCCC)=O
StatusActive (generated by computational methods)
SpeciesMycobacterium tuberculosis
ReferencesLipidomic analyses of Mycobacterium tuberculosis based on accurate mass measurements and the novel "Mtb LipidDB" Mark J. Sartain, Donald L. Dick, Christopher D. Rithner, Dean C. Crick and John T. Belisle, The Journal of Lipid Research, 52, 861-872 (2011).
Calculated physicochemical properties (?):
 Heavy Atoms75Rings3Aromatic Rings0Rotatable Bonds42
 van der Waals
Molecular Volume
1070.50Topological Polar
Surface Area
371.95Hydrogen
Bond Donors
12Hydrogen
Bond Acceptors
23
 logP8.77Molar
Refractivity
278.71    
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.