Structure Database (LMSD)
Common Name
PHDdiA-PS
Systematic Name
1-hexadecanoyl-2-(9-hydroxy-11-carboxy-10E-undecenoyl)-sn-glycero-3-phosphoserine
Synonyms
- 1-palmitoyl-2-(9-hydroxy-11-carboxy-10E-undecenoyl)-sn-glycero-3-phosphoserine
LM ID
LMGP20040003
Status
Active
Exact Mass
Calculate m/z
723.395882
Formula
Abbrev
Main
Classification
Category
Main Class
Sub Class
String Representations
InChiKey (Click to copy)
WSMDTBDFTFYRKA-KEQCEODFSA-N
InChi (Click to copy)
InChI=1S/C34H62NO13P/c1-2-3-4-5-6-7-8-9-10-11-12-15-18-21-32(39)45-25-29(26-46-49(43,44)47-27-30(35)34(41)42)48-33(40)22-19-16-13-14-17-20-28(36)23-24-31(37)38/h23-24,28-30,36H,2-22,25-27,35H2,1H3,(H,37,38)(H,41,42)(H,43,44)/b24-23+/t28?,29-,30+/m1/s1
SMILES (Click to copy)
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(OC(CCCCCCCC(O)/C=C/C(=O)O)=O)COC(CCCCCCCCCCCCCCC)=O)(=O)O
References
Reference
Oxidized Phospholipids as Endogenous Pattern Recognition Ligands in Innate Immunity. Stanley L. Hazen. The Journal of Biological Chemistry. Volume 283, Issue 23, June 2008, pp. 15527-15531. DOI 10.1074/jbc.R700054200.
http://www.jbc.org/content/283/23/15527.full.pdf
http://www.jbc.org/content/283/23/15527.full.pdf
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Mus musculus
(#10090)
Mammalia
(#40674)
Oxidized phospholipids as endogenous pattern recognition ligands in innate immunity.,
J Biol Chem, 2008
J Biol Chem, 2008
Pubmed ID:
18285328
Other Databases
PubChem CID
Calculated Physicochemical Properties
Heavy Atoms
49
Rings
0
Aromatic Rings
0
Rotatable Bonds
36
Van der Waals Molecular Volume
728.66
Topological Polar Surface Area
229.21
Hydrogen Bond Donors
5
Hydrogen Bond Acceptors
14
logP
8.08
Molar Refractivity
186.46
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.
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.