MiMeDB: Showing metabocard for PC(o-18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) (MMDBc0034195)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:20:13 UTC

Update Date

2024-04-30 20:22:28 UTC

Metabolite ID

MMDBc0034195

Metabolite Identification

Common Name

PC(o-18:1(9Z)/20:4(8Z,11Z,14Z,17Z))

Description

PC(O-18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(O-18:1(9Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of Oleyl alcohol at the C-1 position and one chain of eicosatetraenoic acid at the C-2 position. The Oleyl alcohol moiety is derived from beef fat, fish oil, while the eicosatetraenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208022D          

 55 54  0  0  0  0            999 V2000
    0.8033    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9467    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6612    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3757    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0901    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8046    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5191    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    6.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    7.4763    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.9822    7.4763    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   16.6322    7.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    8.3013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    8.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    9.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    9.9513    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.6487    9.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8237   10.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506   10.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5230    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5230    7.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    7.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    8.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    8.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    8.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    7.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    7.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  4  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  4  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 46 45  1  4  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 49 48  1  4  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
M  CHG  2  25  -1  30   1
M  END


  Mrv0541 02251208022D          

 55 54  0  0  0  0            999 V2000
    0.8033    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9467    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6612    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3757    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0901    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8046    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5191    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    6.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    7.4763    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.9822    7.4763    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   16.6322    7.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    8.3013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    8.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    9.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    9.9513    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.6487    9.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8237   10.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506   10.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5230    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5230    7.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    7.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    8.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    8.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    8.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    7.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    7.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  4  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  4  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 46 45  1  4  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 49 48  1  4  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
M  CHG  2  25  -1  30   1
M  END
> <DATABASE_ID>
MMDBc0034195

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCC=CCCCCCCCCOCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC=CCC=CCC=CCC=CCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C46H84NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-46(48)54-45(44-53-55(49,50)52-42-40-47(3,4)5)43-51-41-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h14,16,20-23,25,27,31,33,45H,6-13,15,17-19,24,26,28-30,32,34-44H2,1-5H3

> <INCHI_KEY>
VJNPDLZENXBRLB-UHFFFAOYSA-N

> <FORMULA>
C46H84NO7P

> <MOLECULAR_WEIGHT>
794.1354

> <EXACT_MASS>
793.598540559

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
98.43937839331097

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[2-(icosa-5,8,11,14-tetraenoyloxy)-3-(octadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
6.30

> <JCHEM_LOGP>
9.352395681861589

> <ALOGPS_LOGS>
-7.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550607479243526

> <JCHEM_PKA_STRONGEST_BASIC>
-4.141001480159994

> <JCHEM_POLAR_SURFACE_AREA>
94.12

> <JCHEM_REFRACTIVITY>
249.2995

> <JCHEM_ROTATABLE_BOND_COUNT>
41

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.37e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[2-(icosa-5,8,11,14-tetraenoyloxy)-3-(octadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0       1.499  10.106   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.833   9.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.167  10.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.501   9.336   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.834  10.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.168   9.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.502  10.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.835   9.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.169  10.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.503   9.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.836  10.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.504  10.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.837   9.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.171  10.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.505   9.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.838  10.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.172   9.336   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      25.506  10.106   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      26.839   9.336   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.173  10.106   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.173  11.646   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      29.507  12.416   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0      29.507  13.956   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0      27.967  13.956   0.000  0.00  0.00           O-1
HETATM   26  O   UNK     0      31.047  13.956   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      29.507  15.496   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      30.841  16.266   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.841  17.806   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      32.174  18.576   0.000  0.00  0.00           N+1
HETATM   31  C   UNK     0      32.944  17.242   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      31.404  19.909   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      33.508  19.346   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      29.507   9.336   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      30.841  10.106   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      30.841  11.646   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      32.174   9.336   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      33.508  10.106   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      34.842   9.336   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      36.175  10.106   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      37.509   9.336   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      38.843  10.106   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      38.843  11.646   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      40.176  12.416   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      40.176  13.956   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      38.843  14.726   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      38.843  16.266   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      37.509  17.036   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      36.175  16.266   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      34.842  17.036   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      33.508  16.266   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      33.508  14.726   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      34.842  13.956   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      34.842  12.416   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      36.175  11.646   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   21   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  108    0
END

Synonyms

Not Available

Molecular Formula

C₄₆H₈₄NO₇P

Average Mass

794.1354

Monoisotopic Mass

793.598540559

IUPAC Name

(2-{[2-(icosa-5,8,11,14-tetraenoyloxy)-3-(octadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[2-(icosa-5,8,11,14-tetraenoyloxy)-3-(octadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCC=CCCCCCCCCOCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC=CCC=CCC=CCC=CCCCCC

InChI Identifier

InChI=1S/C46H84NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-46(48)54-45(44-53-55(49,50)52-42-40-47(3,4)5)43-51-41-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h14,16,20-23,25,27,31,33,45H,6-13,15,17-19,24,26,28-30,32,34-44H2,1-5H3

InChI Key

VJNPDLZENXBRLB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-alkyl,2-acylglycero-3-phosphocholines

Alternative Parents

Substituents

1-alkyl,2-acylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Glycerol ether
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.4e-05 g/L	ALOGPS
logP	6.3	ALOGPS
logP	9.35	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	94.12 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	249.3 m³·mol⁻¹	ChemAxon
Polarizability	98.44 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

All Tissues
Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Obesity	Decreased	Association	Human Urine	HMDB	26910390
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	3.40	0.29			umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	HMDB	26910390
Human Blood	Detected and Quantified	22.833	6.419			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Feces	Detected and Quantified	0.07	0.05			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.12	0.1			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	14.4		12.6	17	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	19.3	3.87			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	22.6	6.07			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Urine	Detected and Quantified	5.82	0.61			umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	26910390
Human Blood	Detected and Quantified	6.76		5.6	7.91	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Urine	Detected and Quantified	0.0016	0.003			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	14.9	4.8			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Blood	Detected and Quantified	15.9	3.6			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Urine	Detected and Quantified	0.0062	0.0164			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Saliva	Detected and Quantified	0.025	0.113			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			8.50	36.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human All tissues	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. doi: 10.1016/0092-8674(95)90409-3. [PubMed:7834746 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.

Showing metabocard for PC(o-18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) (MMDBc0034195)

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3D MOL for #<Metabolite:0x00007fdb447d3b98>

3D SDF for #<Metabolite:0x00007fdb447d3b98>

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Structure for #<Metabolite:0x00007fdb447d3b98>

3D Structure for #<Metabolite:0x00007fdb447d3b98>