MiMeDB: Showing metabocard for PC(o-20:0/20:4(8Z,11Z,14Z,17Z)) (MMDBc0034203)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:20:32 UTC

Update Date

2024-04-30 20:22:32 UTC

Metabolite ID

MMDBc0034203

Metabolite Identification

Common Name

PC(o-20:0/20:4(8Z,11Z,14Z,17Z))

Description

PC(O-20:0/20:4(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-20:0/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of Arachidyl alcohol at the C-1 position and one chain of eicosatetraenoic acid at the C-2 position. The Arachidyl alcohol moiety is derived from corn 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 02251208032D          

 57 56  0  0  0  0            999 V2000
   15.3730    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0875    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8020    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5164    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2309    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9454    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6599    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3743    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0888    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8033    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5177    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2322    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9467    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6612    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3756    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0901    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8046    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5190    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2335    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9480    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6624    9.7006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3769    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0914    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0914   10.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8059   10.9381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8059   11.7631    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   30.9809   11.7631    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   32.6309   11.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8059   12.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5203   13.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5203   13.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2348   14.2381    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   33.6473   13.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8223   14.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9493   14.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8059    9.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5203    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5203   10.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2348    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9493    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6637    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3782    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0927    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8072    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8072   10.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5216   10.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5216   11.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8072   12.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8072   13.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0927   13.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3782   13.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6637   13.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9493   13.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9493   12.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6637   11.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6637   10.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3782   10.5256    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
  8  9  1  0  0  0  0
  9 10  1  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
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 23 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 42 41  1  4  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 45 44  1  4  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 48 47  1  4  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 51 50  1  4  0  0  0
 51 52  2  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
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  CHG  2  27  -1  32   1
M  END


  Mrv0541 02251208032D          

 57 56  0  0  0  0            999 V2000
   15.3730    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0875    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8020    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5164    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2309    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9454    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6599    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3743    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0888    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8033    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5177    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2322    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9467    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6612    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3756    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0901    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8046    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5190    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2335    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9480    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6624    9.7006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3769    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0914    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0914   10.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8059   10.9381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8059   11.7631    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   30.9809   11.7631    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   32.6309   11.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8059   12.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5203   13.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5203   13.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2348   14.2381    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   33.6473   13.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8223   14.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9493   14.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8059    9.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5203    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5203   10.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2348    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9493    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6637    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3782    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0927    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8072    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8072   10.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5216   10.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5216   11.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8072   12.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8072   13.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0927   13.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3782   13.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6637   13.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9493   13.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9493   12.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6637   11.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6637   10.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3782   10.5256    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
  8  9  1  0  0  0  0
  9 10  1  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
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 23 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 42 41  1  4  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 45 44  1  4  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 48 47  1  4  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 51 50  1  4  0  0  0
 51 52  2  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
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  CHG  2  27  -1  32   1
M  END
> <DATABASE_ID>
MMDBc0034203

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C48H90NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-43-53-45-47(46-55-57(51,52)54-44-42-49(3,4)5)56-48(50)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,27,29,33,35,47H,6-14,16,18-20,22,24-26,28,30-32,34,36-46H2,1-5H3

> <INCHI_KEY>
RDNHPNJCALITSY-UHFFFAOYSA-N

> <FORMULA>
C48H90NO7P

> <MOLECULAR_WEIGHT>
824.2045

> <EXACT_MASS>
823.645490751

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
103.86352362737814

> <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-(icosyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
6.67

> <JCHEM_LOGP>
10.603454668528256

> <ALOGPS_LOGS>
-7.50

> <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>
257.38489999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
44

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.78e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[2-(icosa-5,8,11,14-tetraenoyloxy)-3-(icosyloxy)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      28.696  18.108   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.030  17.338   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.364  18.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.697  17.338   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      34.031  18.108   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.365  17.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      36.698  18.108   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.032  17.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      39.366  18.108   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      40.699  17.338   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      42.033  18.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      43.367  17.338   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      44.701  18.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      46.034  17.338   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.368  18.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      48.702  17.338   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      50.035  18.108   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      51.369  17.338   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      52.703  18.108   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      54.036  17.338   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      55.370  18.108   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      56.704  17.338   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      58.037  18.108   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      58.037  19.648   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      59.371  20.418   0.000  0.00  0.00           O+0
HETATM   26  P   UNK     0      59.371  21.958   0.000  0.00  0.00           P+0
HETATM   27  O   UNK     0      57.831  21.958   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0      60.911  21.958   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      59.371  23.498   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      60.705  24.268   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      60.705  25.808   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      62.038  26.578   0.000  0.00  0.00           N+1
HETATM   33  C   UNK     0      62.808  25.244   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      61.268  27.912   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      63.372  27.348   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      59.371  17.338   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      60.705  18.108   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      60.705  19.648   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      62.038  17.338   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      63.372  18.108   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      64.706  17.338   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      66.039  18.108   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      67.373  17.338   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      68.707  18.108   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      68.707  19.648   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      70.040  20.418   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      70.040  21.958   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      68.707  22.728   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      68.707  24.268   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      67.373  25.038   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      66.039  24.268   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      64.706  25.038   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      63.372  24.268   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      63.372  22.728   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      64.706  21.958   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      64.706  20.418   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      66.039  19.648   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                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   36                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   23   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   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   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  112    0
END

Synonyms

Not Available

Molecular Formula

C₄₈H₉₀NO₇P

Average Mass

824.2045

Monoisotopic Mass

823.645490751

IUPAC Name

(2-{[2-(icosa-5,8,11,14-tetraenoyloxy)-3-(icosyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[2-(icosa-5,8,11,14-tetraenoyloxy)-3-(icosyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C48H90NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-43-53-45-47(46-55-57(51,52)54-44-42-49(3,4)5)56-48(50)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,27,29,33,35,47H,6-14,16,18-20,22,24-26,28,30-32,34,36-46H2,1-5H3

InChI Key

RDNHPNJCALITSY-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
Dialkyl phosphate
Glycerol ether
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	2.8e-05 g/L	ALOGPS
logP	6.67	ALOGPS
logP	10.6	ChemAxon
logS	-7.5	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	44	ChemAxon
Refractivity	257.38 m³·mol⁻¹	ChemAxon
Polarizability	103.86 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
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	Evidence Type	Host and Biospecimen	Data Source	Reference
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 Blood	Detected and Quantified	3.2221	1.0074			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Feces	Detected and Quantified	0.13	0.07			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.14	0.06			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	1.82		1.47	2.29	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	1.85		1.54	2.19	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	2.40	0.49			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Urine	Detected and Quantified	0.0039	0.0024			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	2.09	0.59			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	2.23	0.48			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	0.0049	0.0041			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 Blood	Detected and Quantified			1.3	4.5	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

75956886

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-20:0/20:4(8Z,11Z,14Z,17Z)) (MMDBc0034203)

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3D Structure for #<Metabolite:0x00007fdb70931450>