MiMeDB: Showing metabocard for PC(o-22:0/22:3(10Z,13Z,16Z)) (MMDBc0034207)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:20:41 UTC

Update Date

2024-04-30 20:22:34 UTC

Metabolite ID

MMDBc0034207

Metabolite Identification

Common Name

PC(o-22:0/22:3(10Z,13Z,16Z))

Description

PC(O-22:0/22:3(10Z,13Z,16Z)) 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-22:0/22:3(10Z,13Z,16Z)), in particular, consists of one chain of Behenyl alcohol at the C-1 position and one chain of (10Z,13Z,16Z-docosatrienoyl) at the C-2 position. The Behenyl alcohol moiety is derived from Rice bran, while the (10Z,13Z,16Z-docosatrienoyl) 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          

 61 60  0  0  0  0            999 V2000
   18.3711   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0855   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8000   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5145   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2289   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9434   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6579   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3724   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0868   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8013   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5158   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2302   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9447   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6592   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3737   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0881   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8026   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5171   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2315   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9460   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6605   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3749   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0894   11.4315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8039   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5184   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5184   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2328   10.1940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2328    9.3690    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   37.0578    9.3690    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   35.4078    9.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2328    8.5440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5184    8.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5184    7.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8039    6.8940    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   34.3914    7.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2164    6.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0894    6.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2328   11.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9473   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9473   10.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6618   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3762   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0907   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8052   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5197   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2341   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9486   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6631   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3775   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0920   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8065   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5210   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5210   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.2354   10.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.9499   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.6644   10.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.3788   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.0933   10.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.8078   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.5223   10.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.2367   10.6065    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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 31 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
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
 25 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 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
 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
 52 51  1  4  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 55 54  1  4  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
M  CHG  2  29  -1  34   1
M  END


  Mrv0541 02251208032D          

 61 60  0  0  0  0            999 V2000
   18.3711   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0855   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8000   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5145   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2289   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9434   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6579   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3724   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0868   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8013   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5158   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2302   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9447   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6592   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3737   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0881   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8026   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5171   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2315   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9460   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6605   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3749   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0894   11.4315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8039   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5184   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5184   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2328   10.1940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2328    9.3690    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   37.0578    9.3690    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   35.4078    9.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2328    8.5440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5184    8.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5184    7.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8039    6.8940    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   34.3914    7.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2164    6.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0894    6.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2328   11.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9473   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9473   10.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6618   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3762   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0907   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8052   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5197   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2341   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9486   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6631   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3775   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0920   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8065   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5210   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5210   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.2354   10.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.9499   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.6644   10.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.3788   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.0933   10.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.8078   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.5223   10.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.2367   10.6065    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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 31 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
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
 25 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 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
 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
 52 51  1  4  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 55 54  1  4  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
M  CHG  2  29  -1  34   1
M  END
> <DATABASE_ID>
MMDBc0034207

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C52H100NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,27,29,51H,6-14,16,18-20,22,24-26,28,30-50H2,1-5H3

> <INCHI_KEY>
CQBVYLALIKLMGX-UHFFFAOYSA-N

> <FORMULA>
C52H100NO7P

> <MOLECULAR_WEIGHT>
882.3267

> <EXACT_MASS>
881.723741071

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
113.23445750027923

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[2-(docosa-10,13,16-trienoyloxy)-3-(docosyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
7.14

> <JCHEM_LOGP>
12.743650985194918

> <ALOGPS_LOGS>
-7.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550607479245658

> <JCHEM_PKA_STRONGEST_BASIC>
-4.141001335677688

> <JCHEM_POLAR_SURFACE_AREA>
94.12

> <JCHEM_REFRACTIVITY>
274.67229999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
49

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[2-(docosa-10,13,16-trienoyloxy)-3-(docosyloxy)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      34.293  21.339   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      35.626  22.109   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      36.960  21.339   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      38.294  22.109   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      39.627  21.339   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      40.961  22.109   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      42.295  21.339   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      43.628  22.109   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.962  21.339   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      46.296  22.109   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      47.629  21.339   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      48.963  22.109   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      50.297  21.339   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      51.631  22.109   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      52.964  21.339   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      54.298  22.109   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      55.632  21.339   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      56.965  22.109   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      58.299  21.339   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      59.633  22.109   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      60.966  21.339   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      62.300  22.109   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      63.634  21.339   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      64.967  22.109   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      66.301  21.339   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      66.301  19.799   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      67.635  19.029   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0      67.635  17.489   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0      69.175  17.489   0.000  0.00  0.00           O-1
HETATM   30  O   UNK     0      66.095  17.489   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      67.635  15.949   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      66.301  15.179   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      66.301  13.639   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      64.967  12.869   0.000  0.00  0.00           N+1
HETATM   35  C   UNK     0      64.197  14.203   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      65.737  11.535   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      63.634  12.099   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      67.635  22.109   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      68.968  21.339   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      68.968  19.799   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      70.302  22.109   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      71.636  21.339   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      72.969  22.109   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      74.303  21.339   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      75.637  22.109   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      76.970  21.339   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      78.304  22.109   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      79.638  21.339   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      80.971  22.109   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      82.305  21.339   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      83.639  22.109   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      84.973  21.339   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      84.973  19.799   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      86.306  19.029   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      87.640  19.799   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      88.974  19.029   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      90.307  19.799   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      91.641  19.029   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      92.975  19.799   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      94.308  19.029   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      95.642  19.799   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                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   38                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34                                                            
CONECT   38   25   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   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   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  120    0
END

Synonyms

Not Available

Molecular Formula

C₅₂H₁₀₀NO₇P

Average Mass

882.3267

Monoisotopic Mass

881.723741071

IUPAC Name

(2-{[2-(docosa-10,13,16-trienoyloxy)-3-(docosyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[2-(docosa-10,13,16-trienoyloxy)-3-(docosyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C52H100NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,27,29,51H,6-14,16,18-20,22,24-26,28,30-50H2,1-5H3

InChI Key

CQBVYLALIKLMGX-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	2.0e-05 g/L	ALOGPS
logP	7.14	ALOGPS
logP	12.74	ChemAxon
logS	-7.7	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	49	ChemAxon
Refractivity	274.67 m³·mol⁻¹	ChemAxon
Polarizability	113.23 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
Eosinophilic esophagitis	Slight Decrease	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	0.203	0.0655			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Urine	Detected and Quantified	0.001		0.0002	0.0031	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected and Quantified	0.06	0.03			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.06	0.03			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	0.12		0.01	0.25	uM	Adolescent (13-18 years old)	Both	Normal	HMDB	28959601
Human Blood	Detected and Quantified	0.12	0.03			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Urine	Detected and Quantified	0.0016	0.001			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	0.101	0.037			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	0.101	0.039			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	0.0024	0.0012			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	0.017	0.002			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			0.050	0.300	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

76043945

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-22:0/22:3(10Z,13Z,16Z)) (MMDBc0034207)

MOL for #<Metabolite:0x00007fdb70750140>

3D MOL for #<Metabolite:0x00007fdb70750140>

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Structure for #<Metabolite:0x00007fdb70750140>

3D Structure for #<Metabolite:0x00007fdb70750140>