MiMeDB: Showing metabocard for PC(P-18:1(11Z)/14:0) (MMDBc0034156)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:18:27 UTC

Update Date

2024-04-30 20:22:04 UTC

Metabolite ID

MMDBc0034156

Metabolite Identification

Common Name

PC(P-18:1(11Z)/14:0)

Description

PC(P-18:1(11Z)/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-18:1(11Z)/14:0), in particular, consists of one chain of plasmalogen 18:1n7 at the C-1 position and one chain of myristic acid at the C-2 position. The plasmalogen 18:1n7 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 02251208002D          

 49 48  0  0  0  0            999 V2000
    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 C   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
   12.0434    6.1283    0.0000 C   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
   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
   18.4737    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 O   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 O   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
   22.7605    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4749    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1894    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9039    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6184    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3328    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0473    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7618    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4762    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1907    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9052    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6197    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6197    6.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3341    7.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3341    8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0486    8.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0486    9.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    4.4783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    3.6533    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.4421    3.6533    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.7921    3.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    2.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    2.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    1.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    1.1783    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   18.7756    1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6006    0.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    0.7658    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  2  0  0  0  0
 14 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
 20 19  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  4  0  0  0
 30 31  2  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
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 17 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
 40 42  2  0  0  0  0
 40 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
 46 48  1  0  0  0  0
 46 49  1  0  0  0  0
M  CHG  2  41  -1  46   1
M  END


  Mrv0541 02251208002D          

 49 48  0  0  0  0            999 V2000
    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 C   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
   12.0434    6.1283    0.0000 C   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
   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
   18.4737    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 O   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 O   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
   22.7605    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4749    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1894    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9039    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6184    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3328    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0473    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7618    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4762    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1907    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9052    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6197    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6197    6.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3341    7.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3341    8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0486    8.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0486    9.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    4.4783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    3.6533    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.4421    3.6533    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.7921    3.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    2.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    2.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    1.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    1.1783    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   18.7756    1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6006    0.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    0.7658    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  2  0  0  0  0
 14 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
 20 19  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  4  0  0  0
 30 31  2  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
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 17 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
 40 42  2  0  0  0  0
 40 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
 46 48  1  0  0  0  0
 46 49  1  0  0  0  0
M  CHG  2  41  -1  46   1
M  END
> <DATABASE_ID>
MMDBc0034156

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCC(=O)OC(COC=CCCCCCCCCC=CCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H78NO7P/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/h16,18,32,35,39H,6-15,17,19-31,33-34,36-38H2,1-5H3

> <INCHI_KEY>
AUJFUAPYFYTPDF-UHFFFAOYSA-N

> <FORMULA>
C40H78NO7P

> <MOLECULAR_WEIGHT>
716.0236

> <EXACT_MASS>
715.551590367

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
88.68155469455897

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trimethyl(2-{[3-(octadeca-1,11-dien-1-yloxy)-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

> <ALOGPS_LOGP>
5.62

> <JCHEM_LOGP>
8.144649363528256

> <ALOGPS_LOGS>
-7.44

> <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>
94.12000000000002

> <JCHEM_REFRACTIVITY>
217.32019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
38

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.77e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyl(2-{[3-(octadeca-1,11-dien-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      17.146  11.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.147  10.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.481  11.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.815  10.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.148  11.439   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.483  11.439   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.151  11.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      34.484   9.129   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      35.818  11.439   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      39.819  10.669   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      41.153  11.439   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      42.486  10.669   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      43.820  11.439   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.154  10.669   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      46.487  11.439   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      47.821  10.669   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      49.155  11.439   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      50.488  10.669   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      51.822  11.439   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      53.156  10.669   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      54.489  11.439   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      55.823  10.669   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      57.157  11.439   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      57.157  12.979   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      58.490  13.749   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      58.490  15.289   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      59.824  16.059   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      59.824  17.599   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      37.152   9.129   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      38.485   8.359   0.000  0.00  0.00           O+0
HETATM   40  P   UNK     0      38.485   6.819   0.000  0.00  0.00           P+0
HETATM   41  O   UNK     0      40.025   6.819   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0      36.945   6.819   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      38.485   5.279   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      37.152   4.509   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      37.152   2.969   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      35.818   2.199   0.000  0.00  0.00           N+1
HETATM   47  C   UNK     0      35.048   3.533   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      36.588   0.866   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      34.484   1.429   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   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   38                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
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                                                            
CONECT   38   17   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42   43                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   40   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48   49                                             
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   46                                                            
MASTER        0    0    0    0    0    0    0    0   49    0   96    0
END

Synonyms

Not Available

Molecular Formula

C₄₀H₇₈NO₇P

Average Mass

716.0236

Monoisotopic Mass

715.551590367

IUPAC Name

trimethyl(2-{[3-(octadeca-1,11-dien-1-yloxy)-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

Traditional Name

trimethyl(2-{[3-(octadeca-1,11-dien-1-yloxy)-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)OC(COC=CCCCCCCCCC=CCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C40H78NO7P/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/h16,18,32,35,39H,6-15,17,19-31,33-34,36-38H2,1-5H3

InChI Key

AUJFUAPYFYTPDF-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	2.8e-05 g/L	ALOGPS
logP	5.62	ALOGPS
logP	8.14	ChemAxon
logS	-7.4	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	38	ChemAxon
Refractivity	217.32 m³·mol⁻¹	ChemAxon
Polarizability	88.68 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		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Microbial Sources

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

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	23.352	12.85			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Urine	Detected and Quantified	0.011				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected and Quantified	0.07	0.07			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.18	0.16			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	10.1		7.46	13.5	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	10.42		0.14	25.10	uM	Adolescent (13-18 years old)	Both	Normal	HMDB	28959601
Human Blood	Detected and Quantified	12.1		9.51	15.8	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	16.6	7.90			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	13.8	6.4			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	18.3	7.6			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
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

76043112

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-18:1(11Z)/14:0) (MMDBc0034156)

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