MiMeDB: Showing metabocard for PC(P-18:0/14:0) (MMDBc0034145)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:17:58 UTC

Update Date

2024-04-30 20:21:57 UTC

Metabolite ID

MMDBc0034145

Metabolite Identification

Common Name

PC(P-18:0/14:0)

Description

PC(P-18:0/14:0) 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(P-18:0/14:0), in particular, consists of one chain of plasmalogen 18:0 at the C-1 position and one chain of myristic acid at the C-2 position. The plasmalogen 18:0 moiety is derived from animal fats, liver and kidney, while the myristic acid moiety is derived from nutmeg and butter. 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. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251207592D          

 49 48  0  0  0  0            999 V2000
    3.4698   16.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4698   16.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842   15.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842   14.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987   14.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987   13.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6132   13.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6132   12.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3276   11.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3276   11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0421   10.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0421    9.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7566    9.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7566    8.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4711    8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4711    7.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855    6.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    4.4783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    3.6533    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684    3.6533    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.2184    3.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    2.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    2.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    1.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    1.1783    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.2020    1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0270    0.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    0.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    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
 17 16  1  4  0  0  0
 17 18  2  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
 24 26  2  0  0  0  0
 24 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
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  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
 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
 48 49  1  0  0  0  0
M  CHG  2  25  -1  30   1
M  END


  Mrv0541 02251207592D          

 49 48  0  0  0  0            999 V2000
    3.4698   16.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4698   16.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842   15.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842   14.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987   14.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987   13.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6132   13.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6132   12.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3276   11.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3276   11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0421   10.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0421    9.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7566    9.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7566    8.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4711    8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4711    7.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855    6.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    4.4783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    3.6533    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684    3.6533    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.2184    3.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    2.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    2.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    1.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    1.1783    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.2020    1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0270    0.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    0.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    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
 17 16  1  4  0  0  0
 17 18  2  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
 24 26  2  0  0  0  0
 24 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
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  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
 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
 48 49  1  0  0  0  0
M  CHG  2  25  -1  30   1
M  END
> <DATABASE_ID>
MMDBc0034145

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCCCCC=COCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C40H80NO7P/c1-6-8-10-12-14-16-18-19-20-21-22-24-26-28-30-32-35-45-37-39(38-47-49(43,44)46-36-34-41(3,4)5)48-40(42)33-31-29-27-25-23-17-15-13-11-9-7-2/h32,35,39H,6-31,33-34,36-38H2,1-5H3

> <INCHI_KEY>
DUKGKTNZVUHGNM-UHFFFAOYSA-N

> <FORMULA>
C40H80NO7P

> <MOLECULAR_WEIGHT>
718.0395

> <EXACT_MASS>
717.567240431

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
91.44015662090862

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trimethyl(2-{[3-(octadec-1-en-1-yloxy)-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
8.506571020194922

> <ALOGPS_LOGS>
-7.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550574852835355

> <JCHEM_PKA_STRONGEST_BASIC>
-4.731743075587598

> <JCHEM_POLAR_SURFACE_AREA>
94.12

> <JCHEM_REFRACTIVITY>
216.2036

> <JCHEM_ROTATABLE_BOND_COUNT>
39

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.50e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyl(2-{[3-(octadec-1-en-1-yloxy)-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

> <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       6.477  31.459   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.477  29.919   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.811  29.149   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.811  27.609   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.144  26.839   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.144  25.299   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.478  24.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.478  22.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.812  22.219   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.812  20.679   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.145  19.909   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.145  18.369   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.479  17.599   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.479  16.059   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.813  15.289   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.813  13.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.146  12.979   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.146  11.439   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.480  10.669   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.147  10.669   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.147   9.129   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.481   8.359   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0      22.481   6.819   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0      24.021   6.819   0.000  0.00  0.00           O-1
HETATM   26  O   UNK     0      20.941   6.819   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      22.481   5.279   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      21.147   4.509   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.147   2.969   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      19.814   2.199   0.000  0.00  0.00           N+1
HETATM   31  C   UNK     0      19.044   3.533   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.584   0.866   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.480   1.429   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      22.481  11.439   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      23.815  10.669   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      23.815   9.129   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      25.148  11.439   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      30.483  11.439   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      33.151  11.439   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      35.818  11.439   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      41.153  11.439   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   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   21   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   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                                                            
MASTER        0    0    0    0    0    0    0    0   49    0   96    0
END

Synonyms

Not Available

Molecular Formula

C₄₀H₈₀NO₇P

Average Mass

718.0395

Monoisotopic Mass

717.567240431

IUPAC Name

trimethyl(2-{[3-(octadec-1-en-1-yloxy)-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

Traditional Name

trimethyl(2-{[3-(octadec-1-en-1-yloxy)-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCC=COCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC

InChI Identifier

InChI=1S/C40H80NO7P/c1-6-8-10-12-14-16-18-19-20-21-22-24-26-28-30-32-35-45-37-39(38-47-49(43,44)46-36-34-41(3,4)5)48-40(42)33-31-29-27-25-23-17-15-13-11-9-7-2/h32,35,39H,6-31,33-34,36-38H2,1-5H3

InChI Key

DUKGKTNZVUHGNM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acyl-glycerophosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl 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-(1Z-alkenyl),2-acyl-glycerophosphocholines

Alternative Parents

Substituents

1-(1z-alkenyl),2-acyl-glycerophosphocholine
Phosphocholine
Glycerol vinyl ether
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
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	2.5e-05 g/L	ALOGPS
logP	5.7	ALOGPS
logP	8.51	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-4.7	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	39	ChemAxon
Refractivity	216.2 m³·mol⁻¹	ChemAxon
Polarizability	91.44 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

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

All Tissues
Blood
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
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Microbial Sources

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

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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	21.468	6.561			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Urine	Detected and Quantified	0.0035		0.0013	0.0071	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	13.6		11.8	15.7	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	13.87		0.11	42.20	uM	Adolescent (13-18 years old)	Both	Normal	HMDB	28959601
Human Blood	Detected and Quantified	15.1	3.01			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	15.3		12.7	18.3	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	10.6	2.7			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	12.5	3.2			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Saliva	Detected and Quantified	0.198	0.349			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human All tissues	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

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

75956956

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(P-18:0/14:0) (MMDBc0034145)

MOL for #<Metabolite:0x000055e071008528>

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3D Structure for #<Metabolite:0x000055e071008528>