MiMeDB: Showing metabocard for PC(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) (MMDBc0034040)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:13:42 UTC

Update Date

2024-04-30 20:20:13 UTC

Metabolite ID

MMDBc0034040

Metabolite Identification

Common Name

PC(20:4(5Z,8Z,11Z,14Z)/16:1(9Z))

Description

PC(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 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(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The arachidonic acid moiety is derived from animal fats and eggs, while the palmitoleic acid moiety is derived from animal fats and vegetable 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.‚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


  Mrv0541 02241223512D          

 55 54  0  0  1  0            999 V2000
   -4.9793    2.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1998    2.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439    3.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643    3.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084    4.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289    4.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    5.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3934    5.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4579    6.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    7.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775    7.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6334    8.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130    8.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5689    9.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3484    9.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    9.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043   10.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839   11.0210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4398   11.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194   12.1012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3753   12.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516   13.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1548   13.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107   13.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0903   14.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2462   15.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0257   15.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1817   16.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5580   16.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139   17.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0903   18.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2462   18.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0257   19.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1817   19.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5580   20.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139   21.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0903   21.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2462   22.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6226   23.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7785   23.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1548   24.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9075   10.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516    9.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3753    9.1307    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.9154    9.7543    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.8352    8.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9989    8.5906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8430    7.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666    7.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107    6.4302    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.5006    6.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209    6.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1548    5.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603   11.5611    0.0000 H   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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  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  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  4  0  0  0
 27 28  2  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
 33 32  1  4  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 36 35  1  4  0  0  0
 36 37  2  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
 19 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
 45 47  2  0  0  0  0
 45 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 51 54  1  0  0  0  0
 19 55  1  1  0  0  0
M  CHG  2  46  -1  51   1
M  END


  Mrv0541 02241223512D          

 55 54  0  0  1  0            999 V2000
   -4.9793    2.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1998    2.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439    3.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643    3.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084    4.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289    4.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    5.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3934    5.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4579    6.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    7.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775    7.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6334    8.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130    8.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5689    9.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3484    9.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    9.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043   10.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839   11.0210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4398   11.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194   12.1012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3753   12.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516   13.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1548   13.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107   13.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0903   14.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2462   15.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0257   15.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1817   16.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5580   16.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139   17.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0903   18.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2462   18.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0257   19.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1817   19.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5580   20.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139   21.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0903   21.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2462   22.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6226   23.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7785   23.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1548   24.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9075   10.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516    9.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3753    9.1307    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.9154    9.7543    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.8352    8.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9989    8.5906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8430    7.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666    7.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107    6.4302    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.5006    6.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209    6.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1548    5.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603   11.5611    0.0000 H   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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  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  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  4  0  0  0
 27 28  2  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
 33 32  1  4  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 36 35  1  4  0  0  0
 36 37  2  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
 19 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
 45 47  2  0  0  0  0
 45 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 51 54  1  0  0  0  0
 19 55  1  1  0  0  0
M  CHG  2  46  -1  51   1
M  END
> <DATABASE_ID>
MMDBc0034040

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C44H78NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-24-19-17-15-13-11-9-7-2/h14,16-17,19-21,23,25,28,30,42H,6-13,15,18,22,24,26-27,29,31-41H2,1-5H3/t42-/m1/s1

> <INCHI_KEY>
KKRYRHYMXROGPM-HUESYALOSA-N

> <FORMULA>
C44H78NO8P

> <MOLECULAR_WEIGHT>
780.0658

> <EXACT_MASS>
779.546504989

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
93.55655280446749

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-(hexadec-9-enoyloxy)-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
8.082462755861588

> <ALOGPS_LOGS>
-7.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550572064467632

> <JCHEM_PKA_STRONGEST_BASIC>
-6.744219009617128

> <JCHEM_POLAR_SURFACE_AREA>
111.19000000000001

> <JCHEM_REFRACTIVITY>
239.85209999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
39

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.09e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-2-(hexadec-9-enoyloxy)-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -9.295   3.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.840   4.442   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.549   5.954   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.093   6.458   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.802   7.970   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.347   8.474   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.056   9.987   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.601  10.491   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.310  12.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.855  12.507   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.564  14.019   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.891  14.524   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.182  16.036   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.638  16.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.929  18.052   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.384  18.556   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.548  17.548   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.675  20.069   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.130  20.573   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.421  22.085   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.876  22.589   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.167  24.101   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.003  25.109   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.622  24.605   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.913  26.117   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.369  26.621   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.660  28.134   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.115  28.638   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.406  30.150   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.242  31.158   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.533  32.671   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.369  33.679   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.660  35.191   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.115  35.695   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.406  37.207   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.242  38.216   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.533  39.728   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.369  40.736   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.660  42.248   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.496  43.256   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.787  44.768   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.622  45.777   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.294  19.564   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       7.003  18.052   0.000  0.00  0.00           O+0
HETATM   45  P   UNK     0       8.167  17.044   0.000  0.00  0.00           P+0
HETATM   46  O   UNK     0       9.175  18.208   0.000  0.00  0.00           O-1
HETATM   47  O   UNK     0       7.159  15.880   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       9.331  16.036   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       9.040  14.524   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      10.204  13.515   0.000  0.00  0.00           C+0
HETATM   51  N   UNK     0       9.913  12.003   0.000  0.00  0.00           N+1
HETATM   52  C   UNK     0       8.401  12.294   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      11.426  11.712   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       9.622  10.491   0.000  0.00  0.00           C+0
HETATM   55  H   UNK     0       4.966  21.581   0.000  0.00  0.00           H+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   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   43   55                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   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   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   19   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47   48                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   45   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   53   54                                             
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54   51                                                            
CONECT   55   19                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  108    0
END

Synonyms

Not Available

Molecular Formula

C₄₄H₇₈NO₈P

Average Mass

780.0658

Monoisotopic Mass

779.546504989

IUPAC Name

(2-{[(2R)-2-(hexadec-9-enoyloxy)-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-(hexadec-9-enoyloxy)-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C44H78NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-24-19-17-15-13-11-9-7-2/h14,16-17,19-21,23,25,28,30,42H,6-13,15,18,22,24,26-27,29,31-41H2,1-5H3/t42-/m1/s1

InChI Key

KKRYRHYMXROGPM-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	3.1e-05 g/L	ALOGPS
logP	5.57	ALOGPS
logP	8.08	ChemAxon
logS	-7.4	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	39	ChemAxon
Refractivity	239.85 m³·mol⁻¹	ChemAxon
Polarizability	93.56 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)	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-17	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

All Tissues
Blood
Feces
Saliva

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	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929

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	42.042	23.098			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Feces	Detected and Quantified	0.06	0.07			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.26	0.5			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	29.3	15.5			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	46.61	21.41			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Blood	Detected and Quantified	5.2		4.18	6.71	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	8.39		6.57	11.5	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	13.5	6.1			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	17.9	7.9			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	0.011	0.001			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

FDB025620

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(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) (MMDBc0034040)

MOL for #<Metabolite:0x00007fecb271f998>

3D MOL for #<Metabolite:0x00007fecb271f998>

3D SDF for #<Metabolite:0x00007fecb271f998>

3D-SDF for #<Metabolite:0x00007fecb271f998>

PDB for #<Metabolite:0x00007fecb271f998>

3D PDB for #<Metabolite:0x00007fecb271f998>

SMILES for #<Metabolite:0x00007fecb271f998>

INCHI for #<Metabolite:0x00007fecb271f998>

Structure for #<Metabolite:0x00007fecb271f998>

3D Structure for #<Metabolite:0x00007fecb271f998>