MiMeDB: Showing metabocard for PC(o-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (MMDBc0034178)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:19:30 UTC

Update Date

2024-04-30 20:22:19 UTC

Metabolite ID

MMDBc0034178

Metabolite Identification

Common Name

PC(o-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))

Description

PC(O-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of palmityl alcohol at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signalling. 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 remodelling 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 be 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. PC(O-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is found in crustaceans and has been isolated from the Japanese oyster Crassostrea gigas.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208012D          

 55 54  0  0  0  0            999 V2000
   10.9461    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6605    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0895    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8039    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5184    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2329    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9474    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6618    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3763    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0908    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8052    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5197    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2342    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9487    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6631    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3776    7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0921    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8065    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8065    6.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5210    5.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5210    5.0822    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.3460    5.0822    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   23.6960    5.0822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5210    4.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8065    3.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8065    3.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0921    2.6072    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   22.6796    3.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5046    1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3776    2.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5210    7.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2355    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2355    6.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6644    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3789    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0934    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8078    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8078    8.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5223    8.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5223    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8078   10.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8078   10.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0934   11.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3789   10.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6644   11.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499   10.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499   10.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2355    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2355    8.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499    8.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6644    8.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6644    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3789   10.0322    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
 22 24  2  0  0  0  0
 22 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  1  0  0  0  0
 28 31  1  0  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  4  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  4  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  4  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 46 45  1  4  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 49 48  1  4  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 52 51  1  4  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
M  CHG  2  23  -1  28   1
M  END


  Mrv0541 02251208012D          

 55 54  0  0  0  0            999 V2000
   10.9461    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6605    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0895    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8039    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5184    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2329    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9474    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6618    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3763    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0908    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8052    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5197    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2342    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9487    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6631    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3776    7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0921    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8065    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8065    6.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5210    5.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5210    5.0822    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.3460    5.0822    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   23.6960    5.0822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5210    4.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8065    3.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8065    3.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0921    2.6072    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   22.6796    3.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5046    1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3776    2.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5210    7.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2355    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2355    6.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6644    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3789    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0934    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8078    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8078    8.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5223    8.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5223    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8078   10.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8078   10.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0934   11.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3789   10.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6644   11.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499   10.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499   10.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2355    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2355    8.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499    8.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6644    8.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6644    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3789   10.0322    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
 22 24  2  0  0  0  0
 22 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  1  0  0  0  0
 28 31  1  0  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  4  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  4  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  4  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 46 45  1  4  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 49 48  1  4  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 52 51  1  4  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
M  CHG  2  23  -1  28   1
M  END
> <DATABASE_ID>
MMDBc0034178

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C46H82NO7P/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/h8,10,14,16,20,22,24-25,27,29,33,35,45H,6-7,9,11-13,15,17-19,21,23,26,28,30-32,34,36-44H2,1-5H3

> <INCHI_KEY>
QQQQNYAHSSIZBU-UHFFFAOYSA-N

> <FORMULA>
C46H82NO7P

> <MOLECULAR_WEIGHT>
792.1195

> <EXACT_MASS>
791.582890495

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
96.13938567976064

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[2-(docosa-4,7,10,13,16,19-hexaenoyloxy)-3-(hexadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
6.29

> <JCHEM_LOGP>
8.990474025194922

> <ALOGPS_LOGS>
-7.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550607478746306

> <JCHEM_PKA_STRONGEST_BASIC>
-4.141005511601818

> <JCHEM_POLAR_SURFACE_AREA>
94.12

> <JCHEM_REFRACTIVITY>
250.4161

> <JCHEM_ROTATABLE_BOND_COUNT>
40

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.71e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[2-(docosa-4,7,10,13,16,19-hexaenoyloxy)-3-(hexadecyloxy)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      20.433  13.337   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.766  14.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.100  13.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.434  14.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.767  13.337   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.101  14.107   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.435  13.337   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.768  14.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.102  13.337   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.436  14.107   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.769  13.337   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.103  14.107   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.437  13.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.771  14.107   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.104  13.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      40.438  14.107   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      41.772  13.337   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      43.105  14.107   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      44.439  13.337   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.439  11.797   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      45.773  11.027   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      45.773   9.487   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      47.313   9.487   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0      44.233   9.487   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      45.773   7.947   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      44.439   7.177   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      44.439   5.637   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      43.105   4.867   0.000  0.00  0.00           N+1
HETATM   29  C   UNK     0      42.335   6.201   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      43.875   3.533   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      41.772   4.097   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      45.773  14.107   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      47.106  13.337   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      47.106  11.797   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      48.440  14.107   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      49.774  13.337   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      51.107  14.107   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      52.441  13.337   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      53.775  14.107   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      53.775  15.647   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      55.108  16.417   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      55.108  17.957   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      53.775  18.727   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      53.775  20.267   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      52.441  21.037   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      51.107  20.267   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      49.774  21.037   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      48.440  20.267   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      48.440  18.727   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      47.106  17.957   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      47.106  16.417   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      48.440  15.647   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      49.774  16.417   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      49.774  17.957   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      51.107  18.727   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   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   19   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   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   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  108    0
END

Synonyms

Not Available

Molecular Formula

C₄₆H₈₂NO₇P

Average Mass

792.1195

Monoisotopic Mass

791.582890495

IUPAC Name

(2-{[2-(docosa-4,7,10,13,16,19-hexaenoyloxy)-3-(hexadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[2-(docosa-4,7,10,13,16,19-hexaenoyloxy)-3-(hexadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCOCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC

InChI Identifier

InChI=1S/C46H82NO7P/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/h8,10,14,16,20,22,24-25,27,29,33,35,45H,6-7,9,11-13,15,17-19,21,23,26,28,30-32,34,36-44H2,1-5H3

InChI Key

QQQQNYAHSSIZBU-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-alkyl,2-acylglycero-3-phosphocholines

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.7e-05 g/L	ALOGPS
logP	6.29	ALOGPS
logP	8.99	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	94.12 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	250.42 m³·mol⁻¹	ChemAxon
Polarizability	96.14 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
Obesity	Decreased	Association	Human Urine	HMDB	26910390
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Microbial Sources

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

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	1.65	0.08			umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	HMDB	26910390
Human Blood	Detected and Quantified	11.0441	3.144			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Urine	Detected and Quantified	0.0065		0.0027	0.017	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	0.13	0.34			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	2.95		2.42	3.51	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Urine	Detected and Quantified	4.26	0.22			umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	26910390
Human Blood	Detected and Quantified	4.5		3.72	5.45	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	7.54		0.03	11.54	uM	Adolescent (13-18 years old)	Both	Normal	HMDB	28959601
Human Blood	Detected and Quantified	8.90	2.29			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	9.88	2.98			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Urine	Detected and Quantified	0.0061	0.0033			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	5.90	2.15			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	6.15	1.84			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	0.0065	0.0053			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			3.30	22.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human All tissues	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22892715

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

2961

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 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..
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-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (MMDBc0034178)

MOL for #<Metabolite:0x00007fdb71fcd998>

3D MOL for #<Metabolite:0x00007fdb71fcd998>

3D SDF for #<Metabolite:0x00007fdb71fcd998>

3D-SDF for #<Metabolite:0x00007fdb71fcd998>

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3D PDB for #<Metabolite:0x00007fdb71fcd998>

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INCHI for #<Metabolite:0x00007fdb71fcd998>

Structure for #<Metabolite:0x00007fdb71fcd998>

3D Structure for #<Metabolite:0x00007fdb71fcd998>