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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:57:12 UTC

Update Date

2022-09-22 17:44:23 UTC

HMDB ID

HMDB0252858

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Glycerylphosphorylcholine

Description

Choline alfoscerate, also known as alphoscerate, choline, belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position. Choline alfoscerate is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Glycerylphosphorylcholine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Glycerylphosphorylcholine 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

HMDB0252858
     RDKit          3D
Glycerylphosphorylcholine
 36 35  0  0  0  0  0  0  0  0999 V2000
   -3.4587   -0.4540   -1.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4371   -0.2028   -0.2908 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8347    1.1590   -0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4595   -1.0673    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810   -0.5610    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1552    0.5375    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1035   -0.0848    0.3018 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1544    0.7814   -0.6801 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.2189    2.1891   -0.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5126    0.8183   -2.2539 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6572    0.0402   -0.7757 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -0.0307    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6007   -0.6546    0.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6806   -1.6982   -0.4544 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6925    0.3321    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6074    0.7930   -1.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245   -1.4676   -1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858    0.2650   -2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4771   -0.3303   -2.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8733    1.3251    1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1645    1.8667   -0.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8387    1.2909   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0284   -2.0957    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4106   -1.0016   -0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5800   -0.7519    1.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -0.8229    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7647   -1.4290   -0.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364    1.2046   -0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1962    1.1471    1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5801   -0.6824    1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525    0.9576    0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8100   -1.0407    1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1971   -2.4794   -0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7194    1.1924    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6626   -0.2004    0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072    1.1553   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  CHG  2   2   1  10  -1
M  END


  Mrv1652305221920472D          

 16 15  0  0  0  0            999 V2000
   -2.8875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    1.4289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 14  5  1  0  0  0  0
 15  7  1  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  CHG  2   9   1  13  -1
M  END
> <DATABASE_ID>
HMDB0252858

> <DATABASE_NAME>
hmdb

> <SMILES>
C[N+](C)(C)CCOP([O-])(=O)OCC(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3

> <INCHI_KEY>
SUHOQUVVVLNYQR-UHFFFAOYSA-N

> <FORMULA>
C8H20NO6P

> <MOLECULAR_WEIGHT>
257.2213

> <EXACT_MASS>
257.102823889

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.818047498402308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.56

> <JCHEM_LOGP>
-5.728311425471745

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.641245557329462

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553451472945346

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9689647678822215

> <JCHEM_POLAR_SURFACE_AREA>
99.05000000000001

> <JCHEM_REFRACTIVITY>
68.6823

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.96e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252858
     RDKit          3D
Glycerylphosphorylcholine
 36 35  0  0  0  0  0  0  0  0999 V2000
   -3.4587   -0.4540   -1.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4371   -0.2028   -0.2908 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8347    1.1590   -0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4595   -1.0673    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810   -0.5610    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1552    0.5375    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1035   -0.0848    0.3018 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1544    0.7814   -0.6801 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.2189    2.1891   -0.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5126    0.8183   -2.2539 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6572    0.0402   -0.7757 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -0.0307    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6007   -0.6546    0.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6806   -1.6982   -0.4544 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6925    0.3321    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6074    0.7930   -1.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245   -1.4676   -1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858    0.2650   -2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4771   -0.3303   -2.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8733    1.3251    1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1645    1.8667   -0.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8387    1.2909   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0284   -2.0957    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4106   -1.0016   -0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5800   -0.7519    1.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -0.8229    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7647   -1.4290   -0.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364    1.2046   -0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1962    1.1471    1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5801   -0.6824    1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525    0.9576    0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8100   -1.0407    1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1971   -2.4794   -0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7194    1.1924    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6626   -0.2004    0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072    1.1553   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  CHG  2   2   1  10  -1
M  END

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -5.390   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.954   1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.286   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -4.620   2.667   0.000  0.00  0.00           N+1
HETATM   10  O   UNK     0       6.160  -2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.620  -0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0      -1.540  -0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    5    9                                                       
CONECT    5    4   14                                                       
CONECT    6    8   10                                                       
CONECT    7    8   15                                                       
CONECT    8    6    7   11                                                  
CONECT    9    1    2    3    4                                             
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12   16                                                            
CONECT   13   16                                                            
CONECT   14    5   16                                                       
CONECT   15    7   16                                                       
CONECT   16   12   13   14   15                                             
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0252858
HETATM    1  C1  UNL     1      -3.459  -0.454  -1.717  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.437  -0.203  -0.291  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -3.835   1.159  -0.050  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.459  -1.067   0.292  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.181  -0.561   0.304  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.155   0.538   0.274  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.103  -0.085   0.302  1.00  0.00           O  
HETATM    8  P1  UNL     1       1.154   0.781  -0.680  1.00  0.00           P  
HETATM    9  O2  UNL     1       1.219   2.189  -0.161  1.00  0.00           O  
HETATM   10  O3  UNL     1       0.513   0.818  -2.254  1.00  0.00           O1-
HETATM   11  O4  UNL     1       2.657   0.040  -0.776  1.00  0.00           O  
HETATM   12  C6  UNL     1       3.233  -0.031   0.484  1.00  0.00           C  
HETATM   13  C7  UNL     1       4.601  -0.655   0.449  1.00  0.00           C  
HETATM   14  O5  UNL     1       4.681  -1.698  -0.454  1.00  0.00           O  
HETATM   15  C8  UNL     1       5.692   0.332   0.122  1.00  0.00           C  
HETATM   16  O6  UNL     1       5.607   0.793  -1.190  1.00  0.00           O  
HETATM   17  H1  UNL     1      -3.125  -1.468  -1.985  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.786   0.265  -2.226  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.477  -0.330  -2.112  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.873   1.325   1.039  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.164   1.867  -0.581  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.839   1.291  -0.501  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.028  -2.096   0.292  1.00  0.00           H  
HETATM   24  H8  UNL     1      -5.411  -1.002  -0.263  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.580  -0.752   1.359  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.384  -0.823   1.367  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.765  -1.429  -0.231  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.236   1.205  -0.598  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.196   1.147   1.212  1.00  0.00           H  
HETATM   30  H14 UNL     1       2.580  -0.682   1.103  1.00  0.00           H  
HETATM   31  H15 UNL     1       3.253   0.958   0.962  1.00  0.00           H  
HETATM   32  H16 UNL     1       4.810  -1.041   1.473  1.00  0.00           H  
HETATM   33  H17 UNL     1       4.197  -2.479  -0.080  1.00  0.00           H  
HETATM   34  H18 UNL     1       5.719   1.192   0.815  1.00  0.00           H  
HETATM   35  H19 UNL     1       6.663  -0.200   0.261  1.00  0.00           H  
HETATM   36  H20 UNL     1       4.707   1.155  -1.333  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4    5
CONECT    3   20   21   22
CONECT    4   23   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   11   12
CONECT   12   13   30   31
CONECT   13   14   15   32
CONECT   14   33
CONECT   15   16   34   35
CONECT   16   36
END

HMDB0252858
     RDKit          3D
Glycerylphosphorylcholine
 36 35  0  0  0  0  0  0  0  0999 V2000
   -3.4587   -0.4540   -1.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4371   -0.2028   -0.2908 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8347    1.1590   -0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4595   -1.0673    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810   -0.5610    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1552    0.5375    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1035   -0.0848    0.3018 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1544    0.7814   -0.6801 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.2189    2.1891   -0.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5126    0.8183   -2.2539 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6572    0.0402   -0.7757 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -0.0307    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6007   -0.6546    0.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6806   -1.6982   -0.4544 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6925    0.3321    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6074    0.7930   -1.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245   -1.4676   -1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858    0.2650   -2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4771   -0.3303   -2.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8733    1.3251    1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1645    1.8667   -0.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8387    1.2909   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0284   -2.0957    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4106   -1.0016   -0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5800   -0.7519    1.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -0.8229    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7647   -1.4290   -0.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364    1.2046   -0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1962    1.1471    1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5801   -0.6824    1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525    0.9576    0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8100   -1.0407    1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1971   -2.4794   -0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7194    1.1924    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6626   -0.2004    0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072    1.1553   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  CHG  2   2   1  10  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Choline alfosceric acid	Generator
Glycerophosphate, choline	MeSH
Alphoscerate, choline	MeSH
Choline glycerophosphate	MeSH
Glycerol 3 phosphocholine	MeSH
3-Phosphocholine, glycerol	MeSH
Glycerophosphorylcholine	MeSH
L alpha Glycerylphosphorylcholine	MeSH
Glycerol 3-phosphocholine	MeSH
Choline alphoscerate	MeSH
Alfoscerate, choline	MeSH
L-alpha-Glycerylphosphorylcholine	MeSH

Chemical Formula

C₈H₂₀NO₆P

Average Molecular Weight

257.2213

Monoisotopic Molecular Weight

257.102823889

IUPAC Name

{2-[(2,3-dihydroxypropyl phosphono)oxy]ethyl}trimethylazanium

Traditional Name

{2-[(2,3-dihydroxypropyl phosphono)oxy]ethyl}trimethylazanium

CAS Registry Number

Not Available

SMILES

C[N+](C)(C)CCOP([O-])(=O)OCC(O)CO

InChI Identifier

InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3

InChI Key

SUHOQUVVVLNYQR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Glycerophosphocholines

Alternative Parents

Substituents

Glycero-3-phosphocholine
Phosphocholine
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
1,2-diol
Secondary alcohol
Organic nitrogen compound
Organic salt
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

a small molecule (L-1-GLYCERO-PHOSPHORYLCHOLINE )

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	-2.6	ALOGPS
logP	-5.7	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	68.68 m³·mol⁻¹	ChemAxon
Polarizability	24.82 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]+	146.962	30932474
DeepCCS	[M-H]-	144.61	30932474
DeepCCS	[M-2H]-	178.298	30932474
DeepCCS	[M+Na]+	152.905	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	152.5	32859911
AllCCS	[M+NH4]+	158.4	32859911
AllCCS	[M+Na]+	159.2	32859911
AllCCS	[M-H]-	162.4	32859911
AllCCS	[M+Na-2H]-	163.5	32859911
AllCCS	[M+HCOO]-	164.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycerylphosphorylcholine	C[N+](C)(C)CCOP([O-])(=O)OCC(O)CO	2647.9	Standard polar	33892256
Glycerylphosphorylcholine	C[N+](C)(C)CCOP([O-])(=O)OCC(O)CO	1594.5	Standard non polar	33892256
Glycerylphosphorylcholine	C[N+](C)(C)CCOP([O-])(=O)OCC(O)CO	1785.0	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 - Glycerylphosphorylcholine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03la-9620000000-b364be629483f7a773d9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerylphosphorylcholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerylphosphorylcholine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerylphosphorylcholine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerylphosphorylcholine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerylphosphorylcholine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerylphosphorylcholine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerylphosphorylcholine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB021802

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-GPC

METLIN ID

Not Available

PubChem Compound

11234

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 ]

Showing metabocard for Glycerylphosphorylcholine (HMDB0252858)

MOL for HMDB0252858 (Glycerylphosphorylcholine)

3D MOL for HMDB0252858 (Glycerylphosphorylcholine)

3D SDF for HMDB0252858 (Glycerylphosphorylcholine)

3D-SDF for HMDB0252858 (Glycerylphosphorylcholine)

PDB for HMDB0252858 (Glycerylphosphorylcholine)

3D PDB for HMDB0252858 (Glycerylphosphorylcholine)

SMILES for HMDB0252858 (Glycerylphosphorylcholine)

INCHI for HMDB0252858 (Glycerylphosphorylcholine)

Structure for HMDB0252858 (Glycerylphosphorylcholine)

3D Structure for HMDB0252858 (Glycerylphosphorylcholine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

NMR Spectra