Structure Database (LMSD)

Common Name
OHOHA-PG
Systematic Name
1-(9Z-octadecenoyl)-2-(4-hydroxy-7-oxo-5E-heptenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)
Synonyms
LM ID
LMGP20060027
Formula
Exact Mass
Calculate m/z
650.343118
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)
AHOPWIMCFHCTSM-HJEVCKDUSA-N
InChi (Click to copy)
InChI=1S/C31H55O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-30(36)40-25-29(26-42-44(38,39)41-24-28(35)23-33)43-31(37)21-20-27(34)18-17-22-32/h9-10,17-18,22,27-29,33-35H,2-8,11-16,19-21,23-26H2,1H3,(H,38,39)/b10-9-,18-17+/t27?,28-,29+/m0/s1
SMILES (Click to copy)
[H][C@](O)(CO)COP(OC[C@]([H])(OC(CCC(O)/C=C/C=O)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)(=O)O

Other Databases

CHEBI ID
PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 44
Rings 0
Aromatic Rings 0
Rotatable Bonds 32
Van der Waals Molecular Volume 656.97
Topological Polar Surface Area 186.12
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 12
logP 7.03
Molar Refractivity 168.92

Admin

Created at
-
Updated at
8th Nov 2024
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.