Structure Database (LMSD)

O HO O O O H O O O H P HO O O HO OH
Common Name
OKHdiA-PG
Systematic Name
1-(9Z-octadecenoyl)-2-(4-oxo-6-carboxy-5E-hexenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)
Synonyms
LM ID
LMGP20060026
Formula
Exact Mass
Calculate m/z
664.322383
Sum Composition
Status
Active

Main

Classification

String Representations

InChiKey (Click to copy)
HPNVNBKGCLPHHJ-OWOATLMESA-N
InChi (Click to copy)
InChI=1S/C31H53O13P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-30(37)41-24-28(25-43-45(39,40)42-23-27(34)22-32)44-31(38)21-19-26(33)18-20-29(35)36/h9-10,18,20,27-28,32,34H,2-8,11-17,19,21-25H2,1H3,(H,35,36)(H,39,40)/b10-9-,20-18+/t27-,28+/m0/s1
SMILES (Click to copy)
[H][C@](O)(CO)COP(OC[C@]([H])(OC(CCC(=O)/C=C/C(=O)O)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)(=O)O

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

Other Databases

PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 45
Rings 0
Aromatic Rings 0
Rotatable Bonds 32
Van der Waals Molecular Volume 663.12
Topological Polar Surface Area 203.19
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 13
logP 6.84
Molar Refractivity 168.98

Admin

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.