MiMeDB: Showing metabocard for PC(18:3(6Z,9Z,12Z)/20:0) (MMDBc0033904)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:08:02 UTC

Update Date

2024-04-30 20:18:31 UTC

Metabolite ID

MMDBc0033904

Metabolite Identification

Common Name

PC(18:3(6Z,9Z,12Z)/20:0)

Description

PC(18:3(6Z,9Z,12Z)/20:0) 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(18:3(6Z,9Z,12Z)/20:0), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of arachidic acid at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the arachidic acid moiety is derived from peanut oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.‚Üµ‚ÜµWhile 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


  Mrv1652303302019592D          

 57 56  0  0  1  0            999 V2000
    9.7086    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2874    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2374   10.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    9.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1105   11.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4230    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5729    5.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8585    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1440    5.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5664    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4295    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7150    5.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9954    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0006    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7099    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2861    5.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4243    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5716    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1388    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8533    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5716    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5677    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8572    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2822    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1427    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9967    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4282    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7112    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7137    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4256    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9993    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1401    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2848    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8546    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5703    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5690    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9355    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7605    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4269    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7124    7.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7124    6.8427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.8559    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5230   10.3342    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   26.8559    5.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835    7.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8230    8.9052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    9.7302    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   26.1414    6.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1730    8.9052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    8.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    6.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    8.9052    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.4269    7.2552    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 22  1  0  0  0  0
 24 21  2  0  0  0  0
 25 23  1  0  0  0  0
 24 26  1  4  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  2  0  0  0  0
 31 29  1  0  0  0  0
 30 32  1  4  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
 38 36  1  0  0  0  0
 39 37  1  0  0  0  0
 41 40  1  0  0  0  0
 44 42  1  0  0  0  0
 44 43  1  0  0  0  0
 45 38  1  0  0  0  0
 46 39  1  0  0  0  0
 47  3  1  0  0  0  0
 47  4  1  0  0  0  0
 47  5  1  0  0  0  0
 47 40  1  0  0  0  0
 48 45  2  0  0  0  0
 49 46  2  0  0  0  0
 52 42  1  0  0  0  0
 52 45  1  0  0  0  0
 53 41  1  0  0  0  0
 54 43  1  0  0  0  0
 44 55  1  6  0  0  0
 55 46  1  0  0  0  0
 56 50  2  0  0  0  0
 56 51  1  0  0  0  0
 56 53  1  0  0  0  0
 56 54  1  0  0  0  0
 44 57  1  6  0  0  0
M  CHG  2  47   1  51  -1
M  END


  Mrv1652303302019592D          

 57 56  0  0  1  0            999 V2000
    9.7086    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2874    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2374   10.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    9.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1105   11.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4230    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5729    5.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8585    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1440    5.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5664    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4295    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7150    5.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9954    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0006    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7099    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2861    5.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4243    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5716    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1388    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8533    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5716    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5677    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8572    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2822    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1427    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9967    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4282    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7112    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7137    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4256    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9993    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1401    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2848    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8546    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5703    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5690    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9355    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7605    9.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4269    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7124    7.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7124    6.8427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.8559    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5230   10.3342    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   26.8559    5.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835    7.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8230    8.9052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    9.7302    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   26.1414    6.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1730    8.9052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    8.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    6.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    8.9052    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.4269    7.2552    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 22  1  0  0  0  0
 24 21  2  0  0  0  0
 25 23  1  0  0  0  0
 24 26  1  4  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  2  0  0  0  0
 31 29  1  0  0  0  0
 30 32  1  4  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
 38 36  1  0  0  0  0
 39 37  1  0  0  0  0
 41 40  1  0  0  0  0
 44 42  1  0  0  0  0
 44 43  1  0  0  0  0
 45 38  1  0  0  0  0
 46 39  1  0  0  0  0
 47  3  1  0  0  0  0
 47  4  1  0  0  0  0
 47  5  1  0  0  0  0
 47 40  1  0  0  0  0
 48 45  2  0  0  0  0
 49 46  2  0  0  0  0
 52 42  1  0  0  0  0
 52 45  1  0  0  0  0
 53 41  1  0  0  0  0
 54 43  1  0  0  0  0
 44 55  1  6  0  0  0
 55 46  1  0  0  0  0
 56 50  2  0  0  0  0
 56 51  1  0  0  0  0
 56 53  1  0  0  0  0
 56 54  1  0  0  0  0
 44 57  1  6  0  0  0
M  CHG  2  47   1  51  -1
M  END
> <DATABASE_ID>
MMDBc0033904

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C46H86NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h15,17,21,24,28,30,44H,6-14,16,18-20,22-23,25-27,29,31-43H2,1-5H3/t44-/m1/s1

> <INCHI_KEY>
ZVIYLLGWTBXCIL-USYZEHPZSA-N

> <FORMULA>
C46H86NO8P

> <MOLECULAR_WEIGHT>
812.1507

> <EXACT_MASS>
811.609105245

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
142

> <JCHEM_AVERAGE_POLARIZABILITY>
99.42589452115358

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-(icosanoyloxy)-3-(octadeca-6,9,12-trienoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
6.08

> <JCHEM_LOGP>
9.695443399194918

> <ALOGPS_LOGS>
-7.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550572064469115

> <JCHEM_PKA_STRONGEST_BASIC>
-6.744160265632107

> <JCHEM_POLAR_SURFACE_AREA>
111.19000000000001

> <JCHEM_REFRACTIVITY>
246.82089999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
43

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.33e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-2-(icosanoyloxy)-3-(octadeca-6,9,12-trienoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

> <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      18.123  12.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      71.470  10.463   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      41.510  20.061   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      38.843  18.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      39.406  20.624   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.456  12.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      70.136   9.693   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.790  12.003   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      68.803  10.463   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.124  12.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      67.469   9.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.457  12.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      66.135  10.463   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.791  12.773   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      64.801   9.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.125  12.003   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      63.468  10.463   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.458  12.773   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      62.134   9.693   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.792  12.003   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      60.800  10.463   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.126  12.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.459  12.003   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      60.800  12.003   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      32.793  12.773   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      59.467  12.773   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      34.127  12.003   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      58.133  12.003   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      35.461  12.773   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      56.799  12.773   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.794  12.003   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      55.466  12.003   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      38.128  12.773   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      54.132  12.773   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      39.462  12.003   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      52.798  12.003   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      40.795  12.773   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      51.465  12.773   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      42.129  12.003   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      40.946  17.957   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      42.486  17.957   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      47.464  12.003   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      46.130  14.313   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      46.130  12.773   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      50.131  12.003   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      43.463  12.773   0.000  0.00  0.00           C+0
HETATM   47  N   UNK     0      40.176  19.291   0.000  0.00  0.00           N+1
HETATM   48  O   UNK     0      50.131  10.463   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      43.463  14.313   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      46.336  16.623   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      44.796  18.163   0.000  0.00  0.00           O-1
HETATM   52  O   UNK     0      48.797  12.773   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      43.256  16.623   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      44.796  15.083   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      44.796  12.003   0.000  0.00  0.00           O+0
HETATM   56  P   UNK     0      44.796  16.623   0.000  0.00  0.00           P+0
HETATM   57  H   UNK     0      47.464  13.543   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   47                                                            
CONECT    4   47                                                            
CONECT    5   47                                                            
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   24                                                       
CONECT   22   20   23                                                       
CONECT   23   22   25                                                       
CONECT   24   21   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   38                                                       
CONECT   37   35   39                                                       
CONECT   38   36   45                                                       
CONECT   39   37   46                                                       
CONECT   40   41   47                                                       
CONECT   41   40   53                                                       
CONECT   42   44   52                                                       
CONECT   43   44   54                                                       
CONECT   44   42   43   55   57                                             
CONECT   45   38   48   52                                                  
CONECT   46   39   49   55                                                  
CONECT   47    3    4    5   40                                             
CONECT   48   45                                                            
CONECT   49   46                                                            
CONECT   50   56                                                            
CONECT   51   56                                                            
CONECT   52   42   45                                                       
CONECT   53   41   56                                                       
CONECT   54   43   56                                                       
CONECT   55   44   46                                                       
CONECT   56   50   51   53   54                                             
CONECT   57   44                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  112    0
END

Synonyms

Not Available

Molecular Formula

C₄₆H₈₆NO₈P

Average Mass

812.1507

Monoisotopic Mass

811.609105245

IUPAC Name

(2-{[(2R)-2-(icosanoyloxy)-3-(octadeca-6,9,12-trienoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-(icosanoyloxy)-3-(octadeca-6,9,12-trienoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C46H86NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h15,17,21,24,28,30,44H,6-14,16,18-20,22-23,25-27,29,31-43H2,1-5H3/t44-/m1/s1

InChI Key

ZVIYLLGWTBXCIL-USYZEHPZSA-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	2.3e-05 g/L	ALOGPS
logP	6.08	ALOGPS
logP	9.7	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	43	ChemAxon
Refractivity	246.82 m³·mol⁻¹	ChemAxon
Polarizability	99.43 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	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2020-06-30	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2020-06-30	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2020-06-30	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2020-06-30	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2020-06-30	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2020-06-30	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

All Tissues
Blood
Feces
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

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
Animal	Milk	Bos taurus	FooDB	Manually Annotated
Animal	Milk	Bos taurus	FooDB	30994344
Animal	Milk	Bos taurus	FooDB	30994344
Animal	Milk	Bos taurus	FooDB	30994344
Animal	Milk	Bos taurus	FooDB	30994344
Animal	Milk	Bos taurus	FooDB	Manually Annotated

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	67.848	22.399			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Urine	Detected and Quantified	0.0056				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected and Quantified	0.12	0.1			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.22	0.32			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	32.8		26.5	38.5	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	36.1		31	41.9	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	47.3	11.3			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	62.34	20.77			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Blood	Detected and Quantified	43.5	14.2			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	56.1	19.7			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	0.050	0.009			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

FDB025365

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]

Showing metabocard for PC(18:3(6Z,9Z,12Z)/20:0) (MMDBc0033904)

MOL for #<Metabolite:0x00007fdb718568e0>

3D MOL for #<Metabolite:0x00007fdb718568e0>

3D SDF for #<Metabolite:0x00007fdb718568e0>

3D-SDF for #<Metabolite:0x00007fdb718568e0>

PDB for #<Metabolite:0x00007fdb718568e0>

3D PDB for #<Metabolite:0x00007fdb718568e0>

SMILES for #<Metabolite:0x00007fdb718568e0>

INCHI for #<Metabolite:0x00007fdb718568e0>

Structure for #<Metabolite:0x00007fdb718568e0>

3D Structure for #<Metabolite:0x00007fdb718568e0>