Structure database (LMSD)

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LM IDLMGP20050034
Common NameOKDdiA-PI
Systematic Name1-(9Z-octadecenoyl)-2-(9-oxo-11-carboxy-10E-undecenoyl)-sn-glycero-3-phospho-
(1'-myo-inositol)
Synonyms-
Exact Mass
822.4167 (neutral)    Calculate m/z:
FormulaC39H67O16P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoinositols [GP2005]
AbbrevPI 30:4;O3
PubChem CID134812451
InChIKeyLQHRICVKSBEXHX-JQZAICAISA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C39H67O16P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-20-23-32(43)52-27-30(54-33(44)24-21-18-15-16-19-22-29(40)25-26-31(41)42)28-53-56(50,51)55-39-37(48)35(46)34(45)36(47)38(39)49/h9-10,25-26,30,34-39,45-49H,2-8,11-24,27-28H2,1H3,(H,41,42)(H,50,51)/b10-9-,26-25+/t30-,34-,35-,36+,37-,38-,39-/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(CCCCCCC/C=C\CCCCCCCC)=O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms56Rings1Aromatic Rings0Rotatable Bonds35
 van der Waals
Molecular Volume
815.53Topological Polar
Surface Area
263.88Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
16
 logP7.48Molar
Refractivity
209.50    
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.