Structure Database (LMSD)

Common Name
OKHdiA-PC
Systematic Name
1-(9Z-octadecenoyl)-2-(4-oxo-6-carboxy-5E-hexenoyl)-sn-glycero-3-phosphocholine
Synonyms
LM ID
LMGP20010032
Status
Active
Exact Mass
Calculate m/z
675.374752
Formula
Abbrev


Download as...
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)
INURYFYRLCBFOH-UHIVKOTGSA-N
InChi (Click to copy)
1S/C33H58NO11P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-32(38)42-27-30(28-44-46(40,41)43-26-25-34(2,3)4)45-33(39)24-22-29(35)21-23-31(36)37/h12-13,21,23,30H,5-11,14-20,22,24-28H2,1-4H3,(H-,36,37,40,41)/b13-12-,23-21+/t30-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC(=O)/C=C/C(=O)O)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O

References

Reference
A Novel Family of Atherogenic Oxidized Phospholipids Promotes Macrophage Foam Cell Formation via the Scavenger Receptor CD36 and Is Enriched in Atherosclerotic Lesions. Eugene A. Podrez, Eugenia Poliakov, Zhongzhou Shen, Renliang Zhang, Yijun Deng, Mingjiang Sun, Paula J. Finton, Lian Shan, Maria Febbraio, David P. Hajjar, Roy L. Silverstein, Henry F. Hoff, Robert G. Salomon, and Stanley L. Hazen. The Journal of Biological Chemistry. Volume 277, Issue 41, October 2002, pp. 38517-38523. DOI 10.1074/jbc.M205924200 http://www.jbc.org/content/277/41/38517

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

Other Databases

PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 46
Rings 0
Aromatic Rings 0
Rotatable Bonds 32
Van der Waals Molecular Volume 691.14
Topological Polar Surface Area 165.56
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 12
logP 7.10
Molar Refractivity 176.19

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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.