Structure Database (LMSD)

Common Name
OKODiA-PC
Systematic Name
1-(9Z-octadecenoyl)-2-(5-oxo-7-carboxy-6E-heptenoyl)-sn-glycero-3-phosphocholine
Synonyms
LM ID
LMGP20010036
Formula
Exact Mass
Calculate m/z
689.390402
Sum Composition
Status
Active

Classification

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
A novel family of atherogenic oxidized phospholipids promotes macrophage foam cell formation via the scavenger receptor CD36 and is enriched in atherosclerotic lesions.,
J Biol Chem, 2002
Pubmed ID: 12145296

String Representations

InChiKey (Click to copy)
WBZDEIQBKMWQFC-PESZKXNGSA-N
InChi (Click to copy)
InChI=1S/C34H60NO11P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-33(39)43-28-31(29-45-47(41,42)44-27-26-35(2,3)4)46-34(40)23-20-21-30(36)24-25-32(37)38/h12-13,24-25,31H,5-11,14-23,26-29H2,1-4H3,(H-,37,38,41,42)/b13-12-,25-24+/t31-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCC(=O)/C=C/C(=O)O)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O

Other Databases

CHEBI ID
PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 47
Rings 0
Aromatic Rings 0
Rotatable Bonds 33
Van der Waals Molecular Volume 708.44
Topological Polar Surface Area 165.56
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 12
logP 7.49
Molar Refractivity 180.81

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Created at
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Updated at
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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.