MiMeDB: Showing metabocard for PC(18:0/18:2(9Z,12Z)) (MMDBc0033811)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:04:17 UTC

Update Date

2024-04-30 20:17:34 UTC

Metabolite ID

MMDBc0033811

Metabolite Identification

Common Name

PC(18:0/18:2(9Z,12Z))

Description

PC(18:0/18:2(9Z,12Z)) 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(18:0/18:2(9Z,12Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the linoleic acid moiety is derived from seed oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303302019572D          

 55 54  0  0  1  0            999 V2000
  -13.0895    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9170   12.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   11.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2751   10.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9731   11.7631    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
   11.9170   11.2697    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
   11.2025   10.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9461    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2025   10.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2316    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4881    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5171    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4881    8.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8026    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7736    8.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0882    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7736    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3737    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0591    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6592    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3447    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9448    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6302    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2303    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9157    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5158    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2012    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8013    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4868    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0869    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7723    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0578    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6579    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3434    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   10.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769   10.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4855    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    8.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    7.5572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9435    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5606   11.0487    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.9435    6.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289    8.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7394    9.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144   10.4447    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2290    7.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0894    9.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144    8.7947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144    7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144    9.6197    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.4855    7.9697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 16  1  0  0  0  0
 17 19  1  4  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  2  0  0  0  0
 24 22  1  0  0  0  0
 23 25  1  4  0  0  0
 26 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
 34 32  1  0  0  0  0
 35 33  1  0  0  0  0
 36 34  1  0  0  0  0
 37 35  1  0  0  0  0
 39 38  1  0  0  0  0
 42 40  1  0  0  0  0
 42 41  1  0  0  0  0
 43 36  1  0  0  0  0
 44 37  1  0  0  0  0
 45  3  1  0  0  0  0
 45  4  1  0  0  0  0
 45  5  1  0  0  0  0
 45 38  1  0  0  0  0
 46 43  2  0  0  0  0
 47 44  2  0  0  0  0
 50 40  1  0  0  0  0
 50 43  1  0  0  0  0
 51 39  1  0  0  0  0
 52 41  1  0  0  0  0
 42 53  1  1  0  0  0
 53 44  1  0  0  0  0
 54 48  2  0  0  0  0
 54 49  1  0  0  0  0
 54 51  1  0  0  0  0
 54 52  1  0  0  0  0
 42 55  1  1  0  0  0
M  CHG  2  45   1  49  -1
M  END


  Mrv1652303302019572D          

 55 54  0  0  1  0            999 V2000
  -13.0895    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9170   12.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   11.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2751   10.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9731   11.7631    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
   11.9170   11.2697    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
   11.2025   10.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9461    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2025   10.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2316    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4881    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5171    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4881    8.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8026    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7736    8.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0882    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7736    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3737    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0591    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6592    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3447    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9448    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6302    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2303    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9157    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5158    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2012    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8013    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4868    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0869    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7723    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0578    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6579    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3434    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   10.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769   10.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4855    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    8.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    7.5572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9435    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5606   11.0487    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.9435    6.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289    8.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7394    9.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144   10.4447    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2290    7.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0894    9.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144    8.7947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144    7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144    9.6197    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.4855    7.9697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 16  1  0  0  0  0
 17 19  1  4  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  2  0  0  0  0
 24 22  1  0  0  0  0
 23 25  1  4  0  0  0
 26 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
 34 32  1  0  0  0  0
 35 33  1  0  0  0  0
 36 34  1  0  0  0  0
 37 35  1  0  0  0  0
 39 38  1  0  0  0  0
 42 40  1  0  0  0  0
 42 41  1  0  0  0  0
 43 36  1  0  0  0  0
 44 37  1  0  0  0  0
 45  3  1  0  0  0  0
 45  4  1  0  0  0  0
 45  5  1  0  0  0  0
 45 38  1  0  0  0  0
 46 43  2  0  0  0  0
 47 44  2  0  0  0  0
 50 40  1  0  0  0  0
 50 43  1  0  0  0  0
 51 39  1  0  0  0  0
 52 41  1  0  0  0  0
 42 53  1  1  0  0  0
 53 44  1  0  0  0  0
 54 48  2  0  0  0  0
 54 49  1  0  0  0  0
 54 51  1  0  0  0  0
 54 52  1  0  0  0  0
 42 55  1  1  0  0  0
M  CHG  2  45   1  49  -1
M  END
> <DATABASE_ID>
MMDBc0033811

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,42H,6-14,16,18-20,22,24-41H2,1-5H3/t42-/m1/s1

> <INCHI_KEY>
FORFDCPQKJHEBF-HUESYALOSA-N

> <FORMULA>
C44H84NO8P

> <MOLECULAR_WEIGHT>
786.1134

> <EXACT_MASS>
785.593455181

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
138

> <JCHEM_AVERAGE_POLARIZABILITY>
98.70370475978638

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trimethyl(2-{[(2R)-2-(octadeca-9,12-dienoyloxy)-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)azanium

> <ALOGPS_LOGP>
5.80

> <JCHEM_LOGP>
9.168227725861586

> <ALOGPS_LOGS>
-7.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550572064469137

> <JCHEM_PKA_STRONGEST_BASIC>
-6.744159309169722

> <JCHEM_POLAR_SURFACE_AREA>
111.19

> <JCHEM_REFRACTIVITY>
236.5023

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.22e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyl(2-{[(2R)-2-(octadeca-9,12-dienoyloxy)-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)azanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAR-20         0                                  
HETATM    1  C   UNK     0     -24.434  14.107   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.245  22.577   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.287  21.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.380  19.854   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.816  21.958   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -23.100  13.337   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.245  21.037   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -21.766  14.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.911  20.267   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -20.433  13.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.911  18.727   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -19.099  14.107   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.578  17.957   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -17.765  13.337   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.578  16.417   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -16.432  14.107   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.244  15.647   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -15.098  13.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.244  14.107   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -13.764  14.107   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.910  13.337   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.431  13.337   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.577  14.107   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -11.097  14.107   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.243  13.337   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.763  13.337   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.909  14.107   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.429  14.107   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.576  13.337   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -7.096  13.337   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.242  14.107   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.762  14.107   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.908  13.337   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.428  13.337   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.575  14.107   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.095  14.107   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.241  13.337   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.276  19.291   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.264  19.291   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.906  13.337   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.240  15.647   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.240  14.107   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -1.761  13.337   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.907  14.107   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0      -1.046  20.624   0.000  0.00  0.00           N+1
HETATM   46  O   UNK     0      -1.761  11.797   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       4.907  15.647   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       5.114  17.957   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       3.574  19.497   0.000  0.00  0.00           O-1
HETATM   50  O   UNK     0      -0.427  14.107   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       2.034  17.957   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       3.574  16.417   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       3.574  13.337   0.000  0.00  0.00           O+0
HETATM   54  P   UNK     0       3.574  17.957   0.000  0.00  0.00           P+0
HETATM   55  H   UNK     0       0.906  14.877   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   45                                                            
CONECT    4   45                                                            
CONECT    5   45                                                            
CONECT    6    1    8                                                       
CONECT    7    2    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   27                                                       
CONECT   26   24   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   30                                                       
CONECT   29   27   31                                                       
CONECT   30   28   32                                                       
CONECT   31   29   33                                                       
CONECT   32   30   34                                                       
CONECT   33   31   35                                                       
CONECT   34   32   36                                                       
CONECT   35   33   37                                                       
CONECT   36   34   43                                                       
CONECT   37   35   44                                                       
CONECT   38   39   45                                                       
CONECT   39   38   51                                                       
CONECT   40   42   50                                                       
CONECT   41   42   52                                                       
CONECT   42   40   41   53   55                                             
CONECT   43   36   46   50                                                  
CONECT   44   37   47   53                                                  
CONECT   45    3    4    5   38                                             
CONECT   46   43                                                            
CONECT   47   44                                                            
CONECT   48   54                                                            
CONECT   49   54                                                            
CONECT   50   40   43                                                       
CONECT   51   39   54                                                       
CONECT   52   41   54                                                       
CONECT   53   42   44                                                       
CONECT   54   48   49   51   52                                             
CONECT   55   42                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  108    0
END

Synonyms

Not Available

Molecular Formula

C₄₄H₈₄NO₈P

Average Mass

786.1134

Monoisotopic Mass

785.593455181

IUPAC Name

trimethyl(2-{[(2R)-2-(octadeca-9,12-dienoyloxy)-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)azanium

Traditional Name

trimethyl(2-{[(2R)-2-(octadeca-9,12-dienoyloxy)-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)azanium

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCCCCC

InChI Identifier

InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,42H,6-14,16,18-20,22,24-41H2,1-5H3/t42-/m1/s1

InChI Key

FORFDCPQKJHEBF-HUESYALOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
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	2.2e-05 g/L	ALOGPS
logP	5.8	ALOGPS
logP	9.17	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	111.19 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	236.5 m³·mol⁻¹	ChemAxon
Polarizability	98.7 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
Placenta
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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0036157	PC(18:0/18:2(9Z,12Z))	Linoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036859	PC(18:0/18:2(9Z,12Z))	Octadecanoate (N-C18:0)	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880

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

Food Exposures

Other Exposures

Source Type	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	279.018	74.520			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Urine	Detected and Quantified	0.016		0.0021	0.045	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected and Quantified	0.84	2			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	1.46	2.13			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	212		183	244	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	250.7	47.2			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	267.03	66.1			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Blood	Detected and Quantified	44.5		37.6	53.3	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	192.7	50.0			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	233.6	68.4			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	0.200	0.031			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
Human Placenta	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

FDB025230

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

168656

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for PC(18:0/18:2(9Z,12Z)) (MMDBc0033811)

MOL for #<Metabolite:0x00007f9250da8470>

3D MOL for #<Metabolite:0x00007f9250da8470>

3D SDF for #<Metabolite:0x00007f9250da8470>

3D-SDF for #<Metabolite:0x00007f9250da8470>

PDB for #<Metabolite:0x00007f9250da8470>

3D PDB for #<Metabolite:0x00007f9250da8470>

SMILES for #<Metabolite:0x00007f9250da8470>

INCHI for #<Metabolite:0x00007f9250da8470>

Structure for #<Metabolite:0x00007f9250da8470>

3D Structure for #<Metabolite:0x00007f9250da8470>