MiMeDB: Showing metabocard for PC(20:0/18:3(6Z,9Z,12Z)) (MMDBc0033955)

Microbial

Human

Animal

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:10:04 UTC

Update Date

2024-04-30 20:18:58 UTC

Metabolite ID

MMDBc0033955

Metabolite Identification

Common Name

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

Description

PC(20:0/18:3(6Z,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(20:0/18:3(6Z,9Z,12Z)), in particular, consists of one chain of arachidic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The arachidic acid moiety is derived from peanut oil, while the g-linolenic acid moiety is derived from animal fats. 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 02251200202D          

 57 56  0  0  1  0            999 V2000
   -9.1811   10.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6625   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8475   10.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3289   11.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5140   11.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9954   11.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1804   11.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6618   12.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8468   12.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3282   12.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133   12.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947   13.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1797   13.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6611   13.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   13.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6725   14.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4874   14.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061   14.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   14.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3396   15.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0433   16.1066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546   15.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6732   15.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4882   15.7217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7845   14.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659   14.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5622   13.5402    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322   13.8365    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.7923   13.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8586   12.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3400   12.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6363   11.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177   10.7171    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.4761   11.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7593   10.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5991   10.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0068   16.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8217   16.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1181   15.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3403   16.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1553   16.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6739   17.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4889   17.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0075   17.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8224   17.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3410   18.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1560   18.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4523   17.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2673   17.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7859   18.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6009   17.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1195   18.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9344   18.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4531   19.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2680   18.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7866   19.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3032   15.5933    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 24 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 44 43  1  4  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 47 46  1  4  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 50 49  1  4  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 24 57  1  6  0  0  0
M  CHG  2  28  -1  33   1
M  END


  Mrv0541 02251200202D          

 57 56  0  0  1  0            999 V2000
   -9.1811   10.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6625   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8475   10.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3289   11.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5140   11.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9954   11.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1804   11.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6618   12.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8468   12.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3282   12.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133   12.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947   13.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1797   13.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6611   13.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   13.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6725   14.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4874   14.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061   14.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   14.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3396   15.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0433   16.1066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546   15.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6732   15.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4882   15.7217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7845   14.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659   14.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5622   13.5402    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322   13.8365    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.7923   13.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8586   12.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3400   12.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6363   11.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177   10.7171    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.4761   11.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7593   10.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5991   10.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0068   16.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8217   16.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1181   15.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3403   16.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1553   16.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6739   17.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4889   17.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0075   17.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8224   17.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3410   18.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1560   18.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4523   17.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2673   17.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7859   18.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6009   17.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1195   18.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9344   18.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4531   19.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2680   18.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7866   19.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3032   15.5933    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 24 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 44 43  1  4  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 47 46  1  4  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 50 49  1  4  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 24 57  1  6  0  0  0
M  CHG  2  28  -1  33   1
M  END
> <DATABASE_ID>
MMDBc0033955

> <DATABASE_NAME>
MIME

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

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

> <INCHI_KEY>
DLZPSAPMHALIOA-USYZEHPZSA-N

> <FORMULA>
C46H86NO8P

> <MOLECULAR_WEIGHT>
812.1507

> <EXACT_MASS>
811.609105245

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
100.11424934341255

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-3-(icosanoyloxy)-2-(octadeca-6,9,12-trienoyloxy)propyl phosphonato]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>
-6.744160237391373

> <JCHEM_POLAR_SURFACE_AREA>
111.19

> <JCHEM_REFRACTIVITY>
246.8209

> <JCHEM_ROTATABLE_BOND_COUNT>
43

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.33e-05 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0     -17.138  18.808   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -16.170  20.005   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.649  19.766   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.681  20.963   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.159  20.724   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.191  21.921   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.670  21.682   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.702  22.880   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.181  22.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.213  23.838   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.691  23.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.723  24.796   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.202  24.556   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.234  25.754   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.287  25.515   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.255  26.712   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.776  26.473   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.745  27.670   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.266  27.431   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.234  28.629   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.681  30.066   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.755  28.389   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.723  29.587   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.245  29.347   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.798  27.910   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.830  26.712   0.000  0.00  0.00           O+0
HETATM   27  P   UNK     0      10.383  25.275   0.000  0.00  0.00           P+0
HETATM   28  O   UNK     0      11.820  25.828   0.000  0.00  0.00           O-1
HETATM   29  O   UNK     0       8.946  24.722   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.936  23.838   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.968  22.640   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.521  21.203   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       9.553  20.005   0.000  0.00  0.00           N+1
HETATM   34  C   UNK     0       8.355  20.973   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.751  19.037   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.585  18.808   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.213  30.545   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.734  30.305   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      13.287  28.868   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      13.702  31.503   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.223  31.263   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      16.191  32.461   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      17.713  32.221   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.681  33.419   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      20.202  33.180   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      21.170  34.377   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      22.691  34.138   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      23.244  32.701   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      24.766  32.461   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      25.734  33.659   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      27.255  33.419   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      28.223  34.617   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      29.744  34.377   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      30.712  35.575   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      32.234  35.335   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      33.202  36.533   0.000  0.00  0.00           C+0
HETATM   57  H   UNK     0      11.766  29.107   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                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   37   57                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   24   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55                                                            
CONECT   57   24                                                            
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)-3-(icosanoyloxy)-2-(octadeca-6,9,12-trienoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

DLZPSAPMHALIOA-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	100.11 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

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-24	188.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	86.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	1208.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	1526.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	2152.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	539.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	5753.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	357.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	432.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1509.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	582.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	288.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	410.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	11.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	376.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	1287.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	856.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	3702.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	4370.9

Retention Indices

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0036234	PC(20:0/18:3(6Z,9Z,12Z))	gamma-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036677	PC(20:0/18:3(6Z,9Z,12Z))	Arachidic acid	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	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

FDB025461

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

CMMC Knowledgebase

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(20:0/18:3(6Z,9Z,12Z)) (MMDBc0033955)

MOL for #<Metabolite:0x00007f9af03ffa88>

3D MOL for #<Metabolite:0x00007f9af03ffa88>

3D SDF for #<Metabolite:0x00007f9af03ffa88>

3D-SDF for #<Metabolite:0x00007f9af03ffa88>

PDB for #<Metabolite:0x00007f9af03ffa88>

3D PDB for #<Metabolite:0x00007f9af03ffa88>

SMILES for #<Metabolite:0x00007f9af03ffa88>

INCHI for #<Metabolite:0x00007f9af03ffa88>

Structure for #<Metabolite:0x00007f9af03ffa88>

3D Structure for #<Metabolite:0x00007f9af03ffa88>