Structure Database (LMSD)

Common Name
PC(O-16:0/9:0(COOH))
Systematic Name
1-hexadecyl-2-(9-carboxy-nonanoyl)-sn-glycero-3-phosphocholine
Synonyms
  • Azelaoyl PAF
  • 1-hexadecyl-2-azelaoyl-sn-glycero-3-phosphocholine
LM ID
LMGP01020279
Status
Active
Exact Mass
Calculate m/z
651.447522
Formula
Abbrev


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MDLMOL SDF CSV TSV
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Main

Classification

String Representations

InChiKey (Click to copy)
ZDFOCDTXDPKJKA-WJOKGBTCSA-N
InChi (Click to copy)
InChI=1S/C33H66NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-16-20-23-27-40-29-31(30-42-44(38,39)41-28-26-34(2,3)4)43-33(37)25-22-19-17-18-21-24-32(35)36/h31H,5-30H2,1-4H3,(H-,35,36,38,39)/t31-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCC(O)=O)=O)COCCCCCCCCCCCCCCCC

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Oxidized alkyl phospholipids are specific, high affinity peroxisome proliferator-activated receptor gamma ligands and agonists.,
J Biol Chem, 2001
Pubmed ID: 11279149

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 44
Rings 0
Aromatic Rings 0
Rotatable Bonds 34
Van der Waals Molecular Volume 684.12
Topological Polar Surface Area 131.42
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 10
logP 9.13
Molar Refractivity 176.34

Reactions

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Admin

Created at
2nd Oct 2020
Updated at
25th Apr 2022
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.