MiMeDB: Showing metabocard for PC(22:0/20:4(8Z,11Z,14Z,17Z)) (MMDBc0034072)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:14:56 UTC

Update Date

2024-04-30 20:20:42 UTC

Metabolite ID

MMDBc0034072

Metabolite Identification

Common Name

PC(22:0/20:4(8Z,11Z,14Z,17Z))

Description

PC(22:0/20:4(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(22:0/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of behenic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The behenic acid moiety is derived from groundnut oil, while the eicsoatetraenoic 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.‚Üµ‚ÜµWhile 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 02251200232D          

 61 60  0  0  1  0            999 V2000
   17.1336   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8480   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5625   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2770   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9914   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7059   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4204   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1349   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8493   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5638   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2783   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9927   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7072   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4217   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1362   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8506   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5651   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2796   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9940   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7085   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4230   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1374   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1374   11.9546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8519   10.7171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5664   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2809   10.7171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   34.2809    9.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5664    9.4796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5664    8.6546    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   34.3914    8.6546    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   32.7414    8.6546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5664    7.8296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8519    7.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8519    6.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1374    6.1796    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   31.7249    6.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5499    5.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4230    5.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9953   11.1296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7098   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7098    9.8921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4243   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1387   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8532   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5677   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2822   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9966   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7111   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4256   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1400   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1400   11.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8545   12.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8545   13.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1400   13.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1400   14.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4256   14.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7111   14.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9966   14.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2822   14.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2822   13.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9954   10.3046    0.0000 H   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  2  0  0  0  0
 22 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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 26 39  1  1  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  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
 54 53  1  4  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 57 56  1  4  0  0  0
 57 58  2  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 26 61  1  6  0  0  0
M  CHG  2  30  -1  35   1
M  END


  Mrv0541 02251200232D          

 61 60  0  0  1  0            999 V2000
   17.1336   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8480   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5625   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2770   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9914   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7059   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4204   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1349   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8493   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5638   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2783   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9927   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7072   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4217   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1362   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8506   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5651   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2796   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9940   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7085   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4230   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1374   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1374   11.9546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8519   10.7171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5664   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2809   10.7171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   34.2809    9.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5664    9.4796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5664    8.6546    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   34.3914    8.6546    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   32.7414    8.6546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5664    7.8296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8519    7.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8519    6.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1374    6.1796    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   31.7249    6.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5499    5.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4230    5.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9953   11.1296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7098   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7098    9.8921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4243   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1387   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8532   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5677   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2822   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9966   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7111   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4256   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1400   11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1400   11.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8545   12.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8545   13.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1400   13.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1400   14.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4256   14.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7111   14.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9966   14.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2822   14.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2822   13.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9954   10.3046    0.0000 H   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  2  0  0  0  0
 22 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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 26 39  1  1  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  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
 54 53  1  4  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 57 56  1  4  0  0  0
 57 58  2  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 26 61  1  6  0  0  0
M  CHG  2  30  -1  35   1
M  END
> <DATABASE_ID>
MMDBc0034072

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC=CCC=CCC=CCC=CCC

> <INCHI_IDENTIFIER>
InChI=1S/C50H92NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-28-30-32-34-36-38-40-42-49(52)56-46-48(47-58-60(54,55)57-45-44-51(3,4)5)59-50(53)43-41-39-37-35-33-31-29-26-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,29,31,48H,6-8,10,12-14,16,18-20,22,24-28,30,32-47H2,1-5H3/t48-/m1/s1

> <INCHI_KEY>
BUDCKLMBPWXPIS-QSCHNALKSA-N

> <FORMULA>
C50H92NO8P

> <MOLECULAR_WEIGHT>
866.2411

> <EXACT_MASS>
865.656055437

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
108.09844664522907

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-3-(docosanoyloxy)-2-(icosa-8,11,14,17-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
6.59

> <JCHEM_LOGP>
11.111796402528253

> <ALOGPS_LOGS>
-7.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550572064469137

> <JCHEM_PKA_STRONGEST_BASIC>
-6.744159309192892

> <JCHEM_POLAR_SURFACE_AREA>
111.19

> <JCHEM_REFRACTIVITY>
266.34149999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
46

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.69e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-3-(docosanoyloxy)-2-(icosa-8,11,14,17-tetraenoyloxy)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      31.983  20.005   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      33.316  20.775   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      34.650  20.005   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      35.984  20.775   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      37.317  20.005   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      38.651  20.775   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      39.985  20.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.318  20.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      42.652  20.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      43.986  20.775   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      45.319  20.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      46.653  20.775   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      47.987  20.005   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      49.321  20.775   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      50.654  20.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      51.988  20.775   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      53.322  20.005   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      54.655  20.775   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      55.989  20.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      57.323  20.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      58.656  20.005   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      59.990  20.775   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      59.990  22.315   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      61.324  20.005   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      62.657  20.775   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      63.991  20.005   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      63.991  18.465   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      62.657  17.695   0.000  0.00  0.00           O+0
HETATM   29  P   UNK     0      62.657  16.155   0.000  0.00  0.00           P+0
HETATM   30  O   UNK     0      64.197  16.155   0.000  0.00  0.00           O-1
HETATM   31  O   UNK     0      61.117  16.155   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      62.657  14.615   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      61.324  13.845   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      61.324  12.305   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      59.990  11.535   0.000  0.00  0.00           N+1
HETATM   36  C   UNK     0      59.220  12.869   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      60.760  10.202   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      58.656  10.765   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      65.325  20.775   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      66.658  20.005   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      66.658  18.465   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      67.992  20.775   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      69.326  20.005   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      70.659  20.775   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      71.993  20.005   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      73.327  20.775   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      74.660  20.005   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      75.994  20.775   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      77.328  20.005   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      78.661  20.775   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      78.661  22.315   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      79.995  23.085   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      79.995  24.625   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      78.661  25.395   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      78.661  26.935   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      77.328  27.705   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      75.994  26.935   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      74.660  27.705   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      73.327  26.935   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      73.327  25.395   0.000  0.00  0.00           C+0
HETATM   61  H   UNK     0      65.325  19.235   0.000  0.00  0.00           H+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   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   39   61                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35                                                            
CONECT   39   26   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   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   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59                                                            
CONECT   61   26                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  120    0
END

Synonyms

Not Available

Molecular Formula

C₅₀H₉₂NO₈P

Average Mass

866.2411

Monoisotopic Mass

865.656055437

IUPAC Name

(2-{[(2R)-3-(docosanoyloxy)-2-(icosa-8,11,14,17-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(docosanoyloxy)-2-(icosa-8,11,14,17-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC=CCC=CCC=CCC=CCC

InChI Identifier

InChI=1S/C50H92NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-28-30-32-34-36-38-40-42-49(52)56-46-48(47-58-60(54,55)57-45-44-51(3,4)5)59-50(53)43-41-39-37-35-33-31-29-26-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,29,31,48H,6-8,10,12-14,16,18-20,22,24-28,30,32-47H2,1-5H3/t48-/m1/s1

InChI Key

BUDCKLMBPWXPIS-QSCHNALKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
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	2.7e-05 g/L	ALOGPS
logP	6.59	ALOGPS
logP	11.11	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	111.19 Å²	ChemAxon
Rotatable Bond Count	46	ChemAxon
Refractivity	266.34 m³·mol⁻¹	ChemAxon
Polarizability	108.1 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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
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

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929

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	0.2922	0.08			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Urine	Detected and Quantified	0.0008		0.0003	0.0025	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected and Quantified	0.02	0.01			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.03	0.01			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	0.18	0.04			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	0.2		0.17	0.23	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	0.24		0.2	0.32	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	0.172	0.059			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	0.185	0.060			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Saliva	Detected and Quantified	0.007	0.001			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
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

FDB025733

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

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]

Showing metabocard for PC(22:0/20:4(8Z,11Z,14Z,17Z)) (MMDBc0034072)

MOL for #<Metabolite:0x00007f46d1e4b820>

3D MOL for #<Metabolite:0x00007f46d1e4b820>

3D SDF for #<Metabolite:0x00007f46d1e4b820>

3D-SDF for #<Metabolite:0x00007f46d1e4b820>

PDB for #<Metabolite:0x00007f46d1e4b820>

3D PDB for #<Metabolite:0x00007f46d1e4b820>

SMILES for #<Metabolite:0x00007f46d1e4b820>

INCHI for #<Metabolite:0x00007f46d1e4b820>

Structure for #<Metabolite:0x00007f46d1e4b820>

3D Structure for #<Metabolite:0x00007f46d1e4b820>