Structure Database (LMSD)

Common Name
OHODiA-PS
Systematic Name
1-(9Z-octadecenoyl)-2-(5-hydroxy-7-carboxy-6E-heptenoyl)-sn-glycero-3-phosphoserine
Synonyms
LM ID
LMGP20040032
Formula
Exact Mass
Calculate m/z
693.348932
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)
JGZJCSRMYKNZFS-XRWGASBYSA-N
InChi (Click to copy)
InChI=1S/C32H56NO13P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-30(37)43-23-27(24-44-47(41,42)45-25-28(33)32(39)40)46-31(38)20-17-18-26(34)21-22-29(35)36/h9-10,21-22,26-28,34H,2-8,11-20,23-25,33H2,1H3,(H,35,36)(H,39,40)(H,41,42)/b10-9-,22-21+/t26?,27-,28+/m1/s1
SMILES (Click to copy)
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(OC(CCCC(O)/C=C/C(=O)O)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)(=O)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 691.42
Topological Polar Surface Area 229.21
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 14
logP 7.08
Molar Refractivity 177.13

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.