Structure database (LMSD)

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LM IDLMGP20050003
Common NamePHDdiA-PI
Systematic Name1-hexadecanoyl-2-(9-hydroxy-11-carboxy-10E-undecenoyl)-sn-glycero-3-phospho-
(1'-myo-inositol)
Synonyms1-palmitoyl-2-(9-hydroxy-11-carboxy-10E-undecenoyl)-sn-glycero-3-phospho-(1'-
myo-inositol)
Exact Mass
798.4167 (neutral)    Calculate m/z:
FormulaC37H67O16P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoinositols [GP2005]
AbbrevPI 28:2;O3
PubChem CID134812420
InChIKeyUWGBODQBJRZZTA-YFWQEGDXSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C37H67O16P/c1-2-3-4-5-6-7-8-9-10-11-12-15-18-21-30(41)50-25-28(52-31(42)22-19-16-13-14-17-20-27(38)23-24-29(39)40)26-51-54(48,49)53-37-35(46)33(44)32(43)34(45)36(37)47/h23-24,27-28,32-38,43-47H,2-22,25-26H2,1H3,(H,39,40)(H,48,49)/b24-23+/t27?,28-,32-,33-,34+,35-,36-,37-/m1/s1
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SMILES
[C@]([H])(OC(CCCCCCCC(O)/C=C/C(=O)O)=O)(COP(=O)(O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O)COC(CCCCCCCCCCCCCCC)=O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms54Rings1Aromatic Rings0Rotatable Bonds34
 van der Waals
Molecular Volume
786.21Topological Polar
Surface Area
267.04Hydrogen
Bond Donors
8Hydrogen
Bond Acceptors
16
 logP7.01Molar
Refractivity
201.88    
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.