MiMeDB: Showing metabocard for PC(o-16:1(9Z)/22:0) (MMDBc0034183)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:19:41 UTC

Update Date

2024-04-30 20:22:22 UTC

Metabolite ID

MMDBc0034183

Metabolite Identification

Common Name

PC(o-16:1(9Z)/22:0)

Description

PC(O-16:1(9Z)/22:0) 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-16:1(9Z)/22:0), in particular, consists of one chain of Palmitoleyl alcohol at the C-1 position and one chain of behenic acid at the C-2 position. The Palmitoleyl alcohol moiety is derived from whale oil, while the behenic acid moiety is derived from groundnut oil. 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 02251208012D          

 55 54  0  0  0  0            999 V2000
   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0894   10.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8039   11.8440    0.0000 O   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
   36.2328   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9473   11.4315    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
   44.8065   12.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5210   13.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5210   13.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.2354   14.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.2354   15.1440    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
  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
 30 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
 36 35  1  4  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 25 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
 46 48  2  0  0  0  0
 46 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 52 55  1  0  0  0  0
M  CHG  2  47  -1  52   1
M  END


  Mrv0541 02251208012D          

 55 54  0  0  0  0            999 V2000
   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0894   10.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8039   11.8440    0.0000 O   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
   36.2328   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9473   11.4315    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
   44.8065   12.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5210   13.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5210   13.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.2354   14.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.2354   15.1440    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
  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
 30 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
 36 35  1  4  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 25 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
 46 48  2  0  0  0  0
 46 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 52 55  1  0  0  0  0
M  CHG  2  47  -1  52   1
M  END
> <DATABASE_ID>
MMDBc0034183

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCC(=O)OC(COCCCCCCCCC=CCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C46H92NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-29-31-33-35-37-39-46(48)54-45(44-53-55(49,50)52-42-40-47(3,4)5)43-51-41-38-36-34-32-30-28-21-19-17-15-13-11-9-7-2/h17,19,45H,6-16,18,20-44H2,1-5H3

> <INCHI_KEY>
BEBNKXDYOOYGGD-UHFFFAOYSA-N

> <FORMULA>
C46H92NO7P

> <MOLECULAR_WEIGHT>
802.1989

> <EXACT_MASS>
801.661140815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
103.11621479118395

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[2-(docosanoyloxy)-3-(hexadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
6.45

> <JCHEM_LOGP>
10.800082308528253

> <ALOGPS_LOGS>
-7.63

> <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>
94.12000000000002

> <JCHEM_REFRACTIVITY>
244.83309999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
45

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.01e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[2-(docosanoyloxy)-3-(hexadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      35.626  22.109   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      36.960  21.339   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      38.294  22.109   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      39.627  21.339   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      40.961  22.109   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      42.295  21.339   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      43.628  22.109   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      44.962  21.339   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      46.296  22.109   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.629  21.339   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      48.963  22.109   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      50.297  21.339   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.631  22.109   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      52.964  21.339   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      54.298  22.109   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      55.632  21.339   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      56.965  22.109   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      58.299  21.339   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      59.633  22.109   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      60.966  21.339   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      62.300  22.109   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      63.634  21.339   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      63.634  19.799   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      64.967  22.109   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      66.301  21.339   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      67.635  22.109   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      68.968  21.339   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      70.302  22.109   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      71.636  21.339   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      72.969  22.109   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      74.303  21.339   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      75.637  22.109   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      76.970  21.339   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      78.304  22.109   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      79.638  21.339   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      80.971  22.109   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      82.305  21.339   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      83.639  22.109   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      83.639  23.649   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      84.973  24.419   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      84.973  25.959   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      86.306  26.729   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      86.306  28.269   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      66.301  19.799   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      67.635  19.029   0.000  0.00  0.00           O+0
HETATM   46  P   UNK     0      67.635  17.489   0.000  0.00  0.00           P+0
HETATM   47  O   UNK     0      69.175  17.489   0.000  0.00  0.00           O-1
HETATM   48  O   UNK     0      66.095  17.489   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      67.635  15.949   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      66.301  15.179   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      66.301  13.639   0.000  0.00  0.00           C+0
HETATM   52  N   UNK     0      64.967  12.869   0.000  0.00  0.00           N+1
HETATM   53  C   UNK     0      64.197  14.203   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      65.737  11.535   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      63.634  12.099   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   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   44                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   25   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48   49                                             
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   46   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53   54   55                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   52                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  108    0
END

Synonyms

Not Available

Molecular Formula

C₄₆H₉₂NO₇P

Average Mass

802.1989

Monoisotopic Mass

801.661140815

IUPAC Name

(2-{[2-(docosanoyloxy)-3-(hexadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[2-(docosanoyloxy)-3-(hexadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCC(=O)OC(COCCCCCCCCC=CCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C46H92NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-29-31-33-35-37-39-46(48)54-45(44-53-55(49,50)52-42-40-47(3,4)5)43-51-41-38-36-34-32-30-28-21-19-17-15-13-11-9-7-2/h17,19,45H,6-16,18,20-44H2,1-5H3

InChI Key

BEBNKXDYOOYGGD-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	6.45	ALOGPS
logP	10.8	ChemAxon
logS	-7.6	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	45	ChemAxon
Refractivity	244.83 m³·mol⁻¹	ChemAxon
Polarizability	103.12 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	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)

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	0.8763	0.4078			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Urine	Detected and Quantified	0.0009		0.0004	0.0022	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected and Quantified	0.04	0.03			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.05	0.05			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	0.80	0.38			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Urine	Detected and Quantified	0.0008	0.0009			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 Urine	Detected and Quantified	0.0013	0.0009			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			0.50	5.50	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

76043909

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-16:1(9Z)/22:0) (MMDBc0034183)

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