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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:28:46 UTC

Update Date

2021-10-01 22:37:29 UTC

HMDB ID

HMDB0254271

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lysophosphatidylcholine

Description

Lysophosphatidylcholine belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Based on a literature review a significant number of articles have been published on Lysophosphatidylcholine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lysophosphatidylcholine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lysophosphatidylcholine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0254271
     RDKit          3D
Lysophosphatidylcholine
 41 40  0  0  0  0  0  0  0  0999 V2000
    7.7910   -1.0917    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -0.3257    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4388    0.9017    0.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3306   -1.0716    0.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779   -0.5807    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134    0.3449    1.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -0.1921    2.4087 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2969    1.0384    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300    0.1515    0.4960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091    0.5118   -0.6036 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.2138   -0.9840   -1.2013 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654    1.1192   -2.0338 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2680    1.2726   -0.5652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    0.9812    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3534    0.3267   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5834   -0.0645   -0.2259 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.4977   -0.8948    0.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2413   -0.8436   -1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4594    1.0902   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8954   -1.7571   -0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7006   -1.6831    1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6570   -0.4290    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    0.0676   -0.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3233   -1.3918   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735    1.1810    1.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6761   -0.9873    2.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179    1.2385   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0291    1.9836    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    1.9784    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866    0.4735    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8327   -0.7323   -0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665    0.8172   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5863   -0.8766    1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3750   -0.6407    1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548   -1.9806    0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0685   -0.3276   -2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3007   -0.9157   -1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7493   -1.8472   -1.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3012    1.5229    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4847    0.7817   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1970    1.8349   -0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
M  CHG  2  12  -1  16   1
M  END

  Mrv1652309112115292D          

 19 18  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -1.1270    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.5243   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677   -1.1270    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.3822   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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  2  0  0  0  0
  9 11  1  0  0  0  0
  9 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
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
  6 19  1  0  0  0  0
M  CHG  2  11  -1  15   1
M  END
> <DATABASE_ID>
HMDB0254271

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H22NO7P/c1-9(12)16-7-10(13)8-18-19(14,15)17-6-5-11(2,3)4/h10,13H,5-8H2,1-4H3

> <INCHI_KEY>
RYCNUMLMNKHWPZ-UHFFFAOYSA-N

> <FORMULA>
C10H22NO7P

> <MOLECULAR_WEIGHT>
299.26

> <EXACT_MASS>
299.11338905

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.017070473081624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[3-(acetyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
-2.40

> <JCHEM_LOGP>
-5.2871860151384125

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.65562406623268

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553406137234658

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039968842188806

> <JCHEM_POLAR_SURFACE_AREA>
105.12

> <JCHEM_REFRACTIVITY>
77.83380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[3-(acetyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254271
     RDKit          3D
Lysophosphatidylcholine
 41 40  0  0  0  0  0  0  0  0999 V2000
    7.7910   -1.0917    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -0.3257    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4388    0.9017    0.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3306   -1.0716    0.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779   -0.5807    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134    0.3449    1.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -0.1921    2.4087 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2969    1.0384    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300    0.1515    0.4960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091    0.5118   -0.6036 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.2138   -0.9840   -1.2013 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654    1.1192   -2.0338 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2680    1.2726   -0.5652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    0.9812    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3534    0.3267   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5834   -0.0645   -0.2259 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.4977   -0.8948    0.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2413   -0.8436   -1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4594    1.0902   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8954   -1.7571   -0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7006   -1.6831    1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6570   -0.4290    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    0.0676   -0.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3233   -1.3918   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735    1.1810    1.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6761   -0.9873    2.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179    1.2385   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0291    1.9836    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    1.9784    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866    0.4735    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8327   -0.7323   -0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665    0.8172   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5863   -0.8766    1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3750   -0.6407    1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548   -1.9806    0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0685   -0.3276   -2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3007   -0.9157   -1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7493   -1.8472   -1.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3012    1.5229    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4847    0.7817   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1970    1.8349   -0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
M  CHG  2  12  -1  16   1
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -0.357  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.976  -3.644   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.311  -2.104   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.645  -1.334   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0       8.978  -2.104   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0       8.208  -3.437   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.748  -0.770   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0      10.312  -2.874   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.646  -2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.979  -2.874   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      14.313  -2.104   0.000  0.00  0.00           N+1
HETATM   16  C   UNK     0      15.647  -1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.083  -3.437   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.543  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.977   0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19    6                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0254271
HETATM    1  C1  UNL     1       7.791  -1.092   0.376  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.508  -0.326   0.247  1.00  0.00           C  
HETATM    3  O1  UNL     1       6.439   0.902   0.136  1.00  0.00           O  
HETATM    4  O2  UNL     1       5.331  -1.072   0.253  1.00  0.00           O  
HETATM    5  C3  UNL     1       4.078  -0.581   0.145  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.513   0.345   1.191  1.00  0.00           C  
HETATM    7  O3  UNL     1       3.319  -0.192   2.409  1.00  0.00           O  
HETATM    8  C5  UNL     1       2.297   1.038   0.523  1.00  0.00           C  
HETATM    9  O4  UNL     1       1.230   0.152   0.496  1.00  0.00           O  
HETATM   10  P1  UNL     1       0.109   0.512  -0.604  1.00  0.00           P  
HETATM   11  O5  UNL     1      -0.214  -0.984  -1.201  1.00  0.00           O  
HETATM   12  O6  UNL     1       0.965   1.119  -2.034  1.00  0.00           O1-
HETATM   13  O7  UNL     1      -1.268   1.273  -0.565  1.00  0.00           O  
HETATM   14  C6  UNL     1      -2.327   0.981   0.241  1.00  0.00           C  
HETATM   15  C7  UNL     1      -3.353   0.327  -0.737  1.00  0.00           C  
HETATM   16  N1  UNL     1      -4.583  -0.065  -0.226  1.00  0.00           N1+
HETATM   17  C8  UNL     1      -4.498  -0.895   0.900  1.00  0.00           C  
HETATM   18  C9  UNL     1      -5.241  -0.844  -1.296  1.00  0.00           C  
HETATM   19  C10 UNL     1      -5.459   1.090  -0.018  1.00  0.00           C  
HETATM   20  H1  UNL     1       7.895  -1.757  -0.514  1.00  0.00           H  
HETATM   21  H2  UNL     1       7.701  -1.683   1.284  1.00  0.00           H  
HETATM   22  H3  UNL     1       8.657  -0.429   0.375  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.052   0.068  -0.822  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.323  -1.392  -0.095  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.274   1.181   1.322  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.676  -0.987   2.372  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.618   1.239  -0.517  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.029   1.984   1.025  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.858   1.978   0.450  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.187   0.473   1.153  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.833  -0.732  -0.958  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.267   0.817  -1.706  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.586  -0.877   1.503  1.00  0.00           H  
HETATM   34  H15 UNL     1      -5.375  -0.641   1.563  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.655  -1.981   0.612  1.00  0.00           H  
HETATM   36  H17 UNL     1      -5.069  -0.328  -2.263  1.00  0.00           H  
HETATM   37  H18 UNL     1      -6.301  -0.916  -1.097  1.00  0.00           H  
HETATM   38  H19 UNL     1      -4.749  -1.847  -1.380  1.00  0.00           H  
HETATM   39  H20 UNL     1      -5.301   1.523   0.969  1.00  0.00           H  
HETATM   40  H21 UNL     1      -6.485   0.782  -0.174  1.00  0.00           H  
HETATM   41  H22 UNL     1      -5.197   1.835  -0.826  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   23   24
CONECT    6    7    8   25
CONECT    7   26
CONECT    8    9   27   28
CONECT    9   10
CONECT   10   11   11   12   13
CONECT   13   14
CONECT   14   15   29   30
CONECT   15   16   31   32
CONECT   16   17   18   19
CONECT   17   33   34   35
CONECT   18   36   37   38
CONECT   19   39   40   41
END

HMDB0254271
     RDKit          3D
Lysophosphatidylcholine
 41 40  0  0  0  0  0  0  0  0999 V2000
    7.7910   -1.0917    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -0.3257    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4388    0.9017    0.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3306   -1.0716    0.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779   -0.5807    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134    0.3449    1.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -0.1921    2.4087 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2969    1.0384    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300    0.1515    0.4960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091    0.5118   -0.6036 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.2138   -0.9840   -1.2013 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654    1.1192   -2.0338 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2680    1.2726   -0.5652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    0.9812    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3534    0.3267   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5834   -0.0645   -0.2259 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.4977   -0.8948    0.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2413   -0.8436   -1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4594    1.0902   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8954   -1.7571   -0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7006   -1.6831    1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6570   -0.4290    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    0.0676   -0.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3233   -1.3918   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735    1.1810    1.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6761   -0.9873    2.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179    1.2385   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0291    1.9836    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    1.9784    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866    0.4735    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8327   -0.7323   -0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665    0.8172   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5863   -0.8766    1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3750   -0.6407    1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548   -1.9806    0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0685   -0.3276   -2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3007   -0.9157   -1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7493   -1.8472   -1.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3012    1.5229    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4847    0.7817   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1970    1.8349   -0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
M  CHG  2  12  -1  16   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₂₂NO₇P

Average Molecular Weight

299.26

Monoisotopic Molecular Weight

299.11338905

IUPAC Name

(2-{[3-(acetyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[3-(acetyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C10H22NO7P/c1-9(12)16-7-10(13)8-18-19(14,15)17-6-5-11(2,3)4/h10,13H,5-8H2,1-4H3

InChI Key

RYCNUMLMNKHWPZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

1-acyl-sn-glycero-3-phosphocholine
Phosphocholine
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Alcohol
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2.4	ALOGPS
logP	-5.3	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	77.83 m³·mol⁻¹	ChemAxon
Polarizability	29.02 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	154.648	30932474
DeepCCS	[M-H]-	152.29	30932474
DeepCCS	[M-2H]-	185.18	30932474
DeepCCS	[M+Na]+	160.742	30932474
AllCCS	[M+H]+	167.2	32859911
AllCCS	[M+H-H2O]+	164.5	32859911
AllCCS	[M+NH4]+	169.8	32859911
AllCCS	[M+Na]+	170.5	32859911
AllCCS	[M-H]-	172.5	32859911
AllCCS	[M+Na-2H]-	173.5	32859911
AllCCS	[M+HCOO]-	174.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lysophosphatidylcholine	CC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C	2768.4	Standard polar	33892256
Lysophosphatidylcholine	CC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C	1677.9	Standard non polar	33892256
Lysophosphatidylcholine	CC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C	1904.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lysophosphatidylcholine GC-MS (Non-derivatized) - 70eV, Positive	splash10-008d-6910000000-216ef7f832568fb7180a	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lysophosphatidylcholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lysophosphatidylcholine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lysophosphatidylcholine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10275055

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lysophosphatidylcholine

METLIN ID

Not Available

PubChem Compound

21668198

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Only showing the first 10 proteins. There are 35 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Acyl-protein thioesterase 1

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:: LYPLA1
Uniprot ID:: O75608
Molecular weight:: 24669.355

Enzyme Details

2. Ectonucleotide pyrophosphatase/phosphodiesterase family member 2

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes lysophospholipids to produce lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine. Also can act on sphingosylphosphphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor.
Gene Name:: ENPP2
Uniprot ID:: Q13822
Molecular weight:: 98992.78

Enzyme Details

3. Peroxiredoxin-6

General function:: Involved in antioxidant activity
Specific function:: Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:: PRDX6
Uniprot ID:: P30041
Molecular weight:: 25034.715

Enzyme Details

4. Group 3 secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Shows an 11-fold preference for phosphatidylglycerol over phosphatidylcholine (PC). Preferential cleavage: 1-palmitoyl-2-linoleoyl-phosphatidylethanolamine (PE) > 1-palmitoyl-2-linoleoyl-PC > 1-palmitoyl-2-arachidonoyl-PC > 1-palmitoyl-2-arachidonoyl-PE. Plays a role in ciliogenesis.
Gene Name:: PLA2G3
Uniprot ID:: Q9NZ20
Molecular weight:: 57166.51

Enzyme Details

5. 1-acyl-sn-glycerol-3-phosphate acyltransferase gamma

General function:: Involved in acyltransferase activity
Specific function:: Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the sn-2 position of the glycerol backbone. Acts on LPA containing saturated or unsaturated fatty acids C16:0-C20:4 at the sn-1 position using C18:1, C20:4 or C18:2-CoA as the acyl donor. Also acts on lysophosphatidylcholine, lysophosphatidylinositol and lysophosphatidylserine using C18:1 or C20:4-CoA.
Gene Name:: AGPAT3
Uniprot ID:: Q9NRZ7
Molecular weight:: 43380.605

Enzyme Details

6. Lysophospholipid acyltransferase 5

General function:: Involved in 1-acylglycerophosphocholine O-acyltransfera
Specific function:: Acyltransferase which mediates the conversion of lysophosphatidylcholine (1-acyl-sn-glycero-3-phosphocholine or LPC) into phosphatidylcholine (1,2-diacyl-sn-glycero-3-phosphocholine or PC) (LPCAT activity). Catalyzes also the conversion of lysophosphatidylserine (1-acyl-2-hydroxy-sn-glycero-3-phospho-L-serine or LPS) into phosphatidylserine (1,2-diacyl-sn-glycero-3-phospho-L-serine or PS) (LPSAT activity). Has also weak lysophosphatidylethanolamine acyltransferase activity (LPEAT activity). Favors polyunsaturated fatty acyl-CoAs as acyl donors compared to saturated fatty acyl-CoAs. Seems to be the major enzyme contributing to LPCAT activity in the liver. Lysophospholipid acyltransferases (LPLATs) catalyze the reacylation step of the phospholipid remodeling pathway also known as the Lands cycle.
Gene Name:: LPCAT3
Uniprot ID:: Q6P1A2
Molecular weight:: 56034.48

Enzyme Details

7. Lysophosphatidylcholine acyltransferase 1

General function:: Involved in acyltransferase activity
Specific function:: Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-independent. Mediates the conversion of 1-acyl-sn-glycero-3-phosphocholine (LPC) into phosphatidylcholine (PC). Displays a clear preference for saturated fatty acyl-CoAs, and 1-myristoyl or 1-palmitoyl LPC as acyl donors and acceptors, respectively. May synthesize phosphatidylcholine in pulmonary surfactant, thereby playing a pivotal role in respiratory physiology.
Gene Name:: LPCAT1
Uniprot ID:: Q8NF37
Molecular weight:: 59150.675

Enzyme Details

8. Lysophosphatidylcholine acyltransferase 2

General function:: Involved in acyltransferase activity
Specific function:: Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-dependent. Involved in platelet-activating factor (PAF) biosynthesis by catalyzing the conversion of the PAF precursor, 1-O-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) into 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine (PAF). Also converts lyso-PAF to 1-alkyl-phosphatidylcholine (PC), a major component of cell membranes and a PAF precursor. Under resting conditions, acyltransferase activity is preferred. Upon acute inflammatory stimulus, acetyltransferase activity is enhanced and PAF synthesis increases (By similarity).
Gene Name:: LPCAT2
Uniprot ID:: Q7L5N7
Molecular weight:: 60207.295

Enzyme Details

9. Abhydrolase domain-containing protein 4

General function:: Involved in hydrolase activity
Specific function:: Lysophospholipase selective for N-acyl phosphatidylethanolamine (NAPE). Contributes to the biosynthesis of N-acyl ethanolamines, including the endocannabinoid anandamide by hydrolyzing the sn-1 and sn-2 acyl chains from N-acyl phosphatidylethanolamine (NAPE) generating glycerophospho-N-acyl ethanolamine (GP-NAE), an intermediate for N-acyl ethanolamine biosynthesis. Hydrolyzes substrates bearing saturated, monounsaturated, polyunsaturated N-acyl chains. Shows no significant activity towards other lysophospholipids, including lysophosphatidylcholine, lysophosphatidylethanolamine and lysophosphatidylserine
Gene Name:: ABHD4
Uniprot ID:: Q8TB40
Molecular weight:: 38794.1

Enzyme Details

10. Lysophospholipid acyltransferase LPCAT4

General function:: Involved in acyltransferase activity
Specific function:: Displays acyl-CoA-dependent lysophospholipid acyltransferase activity with a subset of lysophospholipids as substrates; converts lysophosphatidylethanolamine to phosphatidylethanolamine, lysophosphatidylcholine to phosphatidycholine, 1-alkenyl-lysophatidylethanolamine to 1- alkenyl-phosphatidylethanolamine, lysophosphatidylglycerol and alkyl-lysophosphatidylcholine to phosphatidylglycerol and alkyl- phosphatidylcholine, respectively. In contrast, has no lysophosphatidylinositol, glycerol-3-phosphate, diacylglycerol or lysophosphatidic acid acyltransferase activity. Prefers long chain acyl-CoAs (C16, C18) as acyl donors
Gene Name:: LPCAT4
Uniprot ID:: Q643R3
Molecular weight:: 57218.6

Only showing the first 10 proteins. There are 35 proteins in total.

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Showing metabocard for Lysophosphatidylcholine (HMDB0254271)

MOL for HMDB0254271 (Lysophosphatidylcholine)

3D MOL for HMDB0254271 (Lysophosphatidylcholine)

3D SDF for HMDB0254271 (Lysophosphatidylcholine)

3D-SDF for HMDB0254271 (Lysophosphatidylcholine)

PDB for HMDB0254271 (Lysophosphatidylcholine)

3D PDB for HMDB0254271 (Lysophosphatidylcholine)

SMILES for HMDB0254271 (Lysophosphatidylcholine)

INCHI for HMDB0254271 (Lysophosphatidylcholine)

Structure for HMDB0254271 (Lysophosphatidylcholine)

3D Structure for HMDB0254271 (Lysophosphatidylcholine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

NMR Spectra

Enzymes