Structure Database (LMSD)
Common Name
PC(16:0/20:4(5Z,8Z,10E,14Z)(12OH[S]))
Systematic Name
1-hexadecanoyl-2-(12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
Synonyms
- 16:0/12-HETE PC
- PC(36:4(OH))
- PC(16:0_20:4(OH))
LM ID
LMGP20010002
Formula
Exact Mass
Calculate m/z
797.557072
Sum Composition
Abbrev Chains
PC 16:0_20:4;O
Status
Active
3D model of PC(16:0/20:4(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
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
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
String Representations
InChiKey (Click to copy)
YQWFSBLEXGUMGO-GZXBEVTESA-N
InChi (Click to copy)
InChI=1S/C44H80NO9P/c1-6-8-10-12-14-15-16-17-18-19-23-27-31-35-43(47)51-39-42(40-53-55(49,50)52-38-37-45(3,4)5)54-44(48)36-32-28-24-21-20-22-26-30-34-41(46)33-29-25-13-11-9-7-2/h21-22,24-26,29-30,34,41-42,46H,6-20,23,27-28,31-33,35-40H2,1-5H3/b24-21-,26-22-,29-25-,34-30+/t41-,42+/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(CCCCCCCCCCCCCCC)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
55
Rings
0
Aromatic Rings
0
Rotatable Bonds
40
Van der Waals Molecular Volume
863.86
Topological Polar Surface Area
131.42
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
10
logP
11.96
Molar Refractivity
226.34
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.