Structure Database (LMSD)
Common Name
PC(18:0/20:4(5Z,8Z,10E,14Z)(12OH[S]))
Systematic Name
1-octadecanoyl-2-(12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
Synonyms
- 18:0/12-HETE PC
- PC(38:4(OH))
- PC(18:0_20:4(OH))
LM ID
LMGP20010001
Formula
Exact Mass
Calculate m/z
825.588372
Sum Composition
Abbrev Chains
PC 18:0_20:4;O
Status
Active
3D model of PC(18:0/20:4(5Z,8Z,10E,14Z)(12OH[S]))
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Phospholipid-esterified eicosanoids are generated in agonist-activated human platelets and enhance tissue factor-dependent thrombin generation.,
J Biol Chem, 2010
J Biol Chem, 2010
Pubmed ID:
20061396
Mus musculus
(#10090)
Mammalia
(#40674)
Phosphatidylethanolamine-esterified eicosanoids in the mouse: tissue localization and inflammation-dependent formation in Th-2 disease.,
J Biol Chem, 2009
J Biol Chem, 2009
Pubmed ID:
19531470
String Representations
InChiKey (Click to copy)
YETXCLLSHIMTGE-KDCNQZJWSA-N
InChi (Click to copy)
InChI=1S/C46H84NO9P/c1-6-8-10-12-14-15-16-17-18-19-20-21-25-29-33-37-45(49)53-41-44(42-55-57(51,52)54-40-39-47(3,4)5)56-46(50)38-34-30-26-23-22-24-28-32-36-43(48)35-31-27-13-11-9-7-2/h23-24,26-28,31-32,36,43-44,48H,6-22,25,29-30,33-35,37-42H2,1-5H3/b26-23-,28-24-,31-27-,36-32+/t43-,44+/m0/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC/C=C\C/C=C\C=C\[C@@H](O)C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
57
Rings
0
Aromatic Rings
0
Rotatable Bonds
42
Van der Waals Molecular Volume
898.46
Topological Polar Surface Area
131.42
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
10
logP
12.74
Molar Refractivity
235.57
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.
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.