Structure Database (LMSD)

Common Name
P-LGD2-PC
Systematic Name
1-hexadecanoyl-2-(9,10-seco-9,11-dioxo-15-hydroxy-5Z,13E-prostadienoyl)-sn-glycero-phosphocholine
Synonyms
  • -
LM ID
LMGP20010050
Status
Active
Exact Mass
Calculate m/z
829.546902
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)
CIZJGRKAYDGGIP-SVCIMYNVSA-N
InChi (Click to copy)
InChI=1S/C44H80NO11P/c1-7-9-11-12-13-14-15-16-17-18-19-20-25-29-43(49)53-36-41(37-55-57(51,52)54-34-33-45(4,5)6)56-44(50)30-26-22-21-24-27-39(35-46)42(38(3)47)32-31-40(48)28-23-10-8-2/h21,24,31-32,35,39-42,48H,7-20,22-23,25-30,33-34,36-37H2,1-6H3/b24-21-,32-31+/t39?,40?,41-,42?/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC/C=C\CC(C=O)C(/C=C/C(O)CCCCC)C(C)=O)=O)COC(CCCCCCCCCCCCCCC)=O

References

Reference
Oxidized phospholipids: From molecular properties to disease.Gilbert O. Fruhwirth, Alexandra Loidl and Albin Hermetter.Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease. Volume 1772, Issue 7, July 2007, Pages 718-736. doi.org/10.1016/j.bbadis.2007.04.009

https://www.sciencedirect.com/science/article/pii/S0925443907001032?via%3Dihub

Other Databases

PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 57
Rings 0
Aromatic Rings 0
Rotatable Bonds 41
Van der Waals Molecular Volume 881.44
Topological Polar Surface Area 165.56
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 12
logP 10.48
Molar Refractivity 227.17

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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.