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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (15) Show 15 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 UTC

HMDB ID

HMDB0000086

Secondary Accession Numbers

HMDB0000049
HMDB00049
HMDB00086

Metabolite Identification

Common Name

Glycerophosphocholine

Description

Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release. GPC is formed in the breakdown of phosphatidylcholine (PtC). This pathway is active in many body tissues, including mammary tissue.

Structure

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

HMDB0000086
     RDKit          3D
Glycerophosphocholine
 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.1516   -0.4168    1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648    0.0678    0.3124 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2136    1.4936    0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6555   -0.3739   -0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262   -0.5294    0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7030    0.2997    0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4340    0.5623   -0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8533   -0.3893   -1.4589 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6836   -1.7510   -0.8004 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688   -0.6174   -3.1183 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.3297    0.3206   -0.9995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0864   -0.6739   -0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5306   -0.2983   -0.2179 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1575   -1.3948    0.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7108    0.8939    0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644    2.0551   -0.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1133   -1.5322    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7702   -0.1950    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1578   -0.0170    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    1.8605    1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610    2.0070    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9107    1.8701   -0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011   -0.0415   -1.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6333    0.1548   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793   -1.4551   -0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079   -0.8825    1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8045   -1.4545    0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6512    1.2076    1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -0.3268    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0742   -1.5798   -1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6153   -0.9537    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670   -0.1239   -1.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7271   -2.2092    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6891    0.7992    1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9147    0.9948    1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704    2.6291    0.0596 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  6
 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


  Mrv1652305271900142D          

 16 15  0  0  1  0            999 V2000
    9.1187   -4.3982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5477   -4.3905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3992   -3.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2567   -4.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6795   -4.3954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9678   -4.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9599   -3.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6795   -5.2099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6805   -4.0236    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.2403   -4.3961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3945   -4.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6805   -3.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8310   -3.9819    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.8266   -3.1570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8310   -4.8069    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.3949   -3.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  6  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  1 13  1  0  0  0  0
 13  2  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 16  1  0  0  0  0
M  CHG  2   9   1  15  -1
M  END
> <DATABASE_ID>
HMDB0000086

> <DATABASE_NAME>
hmdb

> <SMILES>
C[N+](C)(C)CCOP([O-])(=O)OC[C@H](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/t8-/m1/s1

> <INCHI_KEY>
SUHOQUVVVLNYQR-MRVPVSSYSA-N

> <FORMULA>
C8H20NO6P

> <MOLECULAR_WEIGHT>
257.223

> <EXACT_MASS>
257.102824366

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.772342802488055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000086
     RDKit          3D
Glycerophosphocholine
 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.1516   -0.4168    1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648    0.0678    0.3124 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2136    1.4936    0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6555   -0.3739   -0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262   -0.5294    0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7030    0.2997    0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4340    0.5623   -0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8533   -0.3893   -1.4589 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6836   -1.7510   -0.8004 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688   -0.6174   -3.1183 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.3297    0.3206   -0.9995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0864   -0.6739   -0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5306   -0.2983   -0.2179 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1575   -1.3948    0.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7108    0.8939    0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644    2.0551   -0.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1133   -1.5322    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7702   -0.1950    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1578   -0.0170    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    1.8605    1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610    2.0070    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9107    1.8701   -0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011   -0.0415   -1.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6333    0.1548   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793   -1.4551   -0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079   -0.8825    1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8045   -1.4545    0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6512    1.2076    1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -0.3268    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0742   -1.5798   -1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6153   -0.9537    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670   -0.1239   -1.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7271   -2.2092    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6891    0.7992    1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9147    0.9948    1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704    2.6291    0.0596 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  6
 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                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      17.022  -8.210   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      19.689  -8.196   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.679  -7.444   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.013  -7.468   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.335  -8.205   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.340  -8.249   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.992  -7.439   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.335  -9.725   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      23.670  -7.511   0.000  0.00  0.00           N+1
HETATM   10  O   UNK     0      11.649  -8.206   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      25.003  -8.295   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.670  -5.997   0.000  0.00  0.00           C+0
HETATM   13  P   UNK     0      18.351  -7.433   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      18.343  -5.893   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      18.351  -8.973   0.000  0.00  0.00           O-1
HETATM   16  C   UNK     0      25.004  -6.741   0.000  0.00  0.00           C+0
CONECT    1    3   13                                                       
CONECT    2    4   13                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7    8                                                  
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8    5                                                            
CONECT    9    6   11   12   16                                             
CONECT   10    7                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    1    2   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0000086
HETATM    1  C1  UNL     1      -4.152  -0.417   1.279  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.165   0.068   0.312  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -3.214   1.494   0.336  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.656  -0.374  -0.992  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.926  -0.529   0.676  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.703   0.300   0.461  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.434   0.562  -0.880  1.00  0.00           O  
HETATM    8  P1  UNL     1       0.853  -0.389  -1.459  1.00  0.00           P  
HETATM    9  O2  UNL     1       0.684  -1.751  -0.800  1.00  0.00           O  
HETATM   10  O3  UNL     1       0.769  -0.617  -3.118  1.00  0.00           O1-
HETATM   11  O4  UNL     1       2.330   0.321  -0.999  1.00  0.00           O  
HETATM   12  C6  UNL     1       3.086  -0.674  -0.408  1.00  0.00           C  
HETATM   13  C7  UNL     1       4.531  -0.298  -0.218  1.00  0.00           C  
HETATM   14  O5  UNL     1       5.157  -1.395   0.391  1.00  0.00           O  
HETATM   15  C8  UNL     1       4.711   0.894   0.681  1.00  0.00           C  
HETATM   16  O6  UNL     1       4.764   2.055  -0.079  1.00  0.00           O  
HETATM   17  H1  UNL     1      -4.113  -1.532   1.190  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.770  -0.195   2.301  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.158  -0.017   1.091  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.662   1.860   1.294  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.261   2.007   0.162  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.911   1.870  -0.456  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.001  -0.042  -1.811  1.00  0.00           H  
HETATM   24  H8  UNL     1      -4.633   0.155  -1.127  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.879  -1.455  -0.999  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.908  -0.883   1.736  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.805  -1.455   0.061  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.651   1.208   1.098  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.158  -0.327   0.814  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.074  -1.580  -1.065  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.615  -0.954   0.565  1.00  0.00           H  
HETATM   32  H16 UNL     1       4.967  -0.124  -1.227  1.00  0.00           H  
HETATM   33  H17 UNL     1       4.727  -2.209   0.001  1.00  0.00           H  
HETATM   34  H18 UNL     1       5.689   0.799   1.211  1.00  0.00           H  
HETATM   35  H19 UNL     1       3.915   0.995   1.435  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.970   2.629   0.060  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

HMDB0000086
     RDKit          3D
Glycerophosphocholine
 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.1516   -0.4168    1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648    0.0678    0.3124 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2136    1.4936    0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6555   -0.3739   -0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262   -0.5294    0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7030    0.2997    0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4340    0.5623   -0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8533   -0.3893   -1.4589 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6836   -1.7510   -0.8004 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688   -0.6174   -3.1183 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.3297    0.3206   -0.9995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0864   -0.6739   -0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5306   -0.2983   -0.2179 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1575   -1.3948    0.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7108    0.8939    0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644    2.0551   -0.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1133   -1.5322    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7702   -0.1950    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1578   -0.0170    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    1.8605    1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610    2.0070    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9107    1.8701   -0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011   -0.0415   -1.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6333    0.1548   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793   -1.4551   -0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079   -0.8825    1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8045   -1.4545    0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6512    1.2076    1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -0.3268    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0742   -1.5798   -1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6153   -0.9537    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670   -0.1239   -1.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7271   -2.2092    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6891    0.7992    1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9147    0.9948    1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704    2.6291    0.0596 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  6
 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
(2R)-2,3-Dihydroxypropyl 2-(trimethylammonio)ethyl phosphate	ChEBI
Alfoscerate de choline	ChEBI
Alfoscerato de colina	ChEBI
alpha-Glycerophosphorylcholine	ChEBI
Choline alphoscerate	ChEBI
Choline glycerophosphate	ChEBI
Cholini alfosceras	ChEBI
Cholini glycerophosphas	ChEBI
Glicerofosfato de colina	ChEBI
Glycerol phosphorylcholine	ChEBI
Glycerol-3-phosphatidylcholine	ChEBI
Glycerol-3-phosphocholine	ChEBI
Glycerophosphate de choline	ChEBI
Glycerophosphorylcholine	ChEBI
GPCho	ChEBI
L-alpha-Glycerophosphocholine	ChEBI
L-alpha-Glycerophosphorylcholine	ChEBI
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt	ChEBI
sn-3-GPC	ChEBI
sn-Glycero-3-phosphocholine	ChEBI
sn-Glycerol 3-phosphocholine	ChEBI
Gliatilin	Kegg
(2R)-2,3-Dihydroxypropyl 2-(trimethylammonio)ethyl phosphoric acid	Generator
Alfosceric acid de choline	Generator
a-Glycerophosphorylcholine	Generator
Α-glycerophosphorylcholine	Generator
Choline alphosceric acid	Generator
Choline glycerophosphoric acid	Generator
Glycerophosphoric acid de choline	Generator
L-a-Glycerophosphocholine	Generator
L-Α-glycerophosphocholine	Generator
L-a-Glycerophosphorylcholine	Generator
L-Α-glycerophosphorylcholine	Generator
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphoric acid inner salt	Generator
Choline alfosceric acid	HMDB
Glycerol 3 phosphocholine	HMDB
Glycerylphosphorylcholine	HMDB
Alphoscerate, choline	HMDB
L alpha Glycerylphosphorylcholine	HMDB
3-Phosphocholine, glycerol	HMDB
Glycerol 3-phosphocholine	HMDB
L-alpha-Glycerylphosphorylcholine	HMDB
Alfoscerate, choline	HMDB
Glycerophosphate, choline	HMDB
2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium inner salt	HMDB
a-Glycerylphosphorylcholine	HMDB
alpha-Glycerylphosphorylcholine	HMDB
Choline alfoscerate	HMDB
Glycerophosphatidylcholine	HMDB
GPC	HMDB
Hydrogen glycerophosphate choline	HMDB
Cereton	HMDB
Cholicerin	HMDB
Cholitiline	HMDB
Delecit	HMDB
Glycerol 3-phosphorylcholine	HMDB
Glycerophosphoric acid choline ester	HMDB
Glyceryl 3-phosphorylcholine	HMDB
Glycerylphosphocholine	HMDB
L-alpha-GPC	HMDB
L-Α-GPC	HMDB
L-Α-glycerylphosphorylcholine	HMDB
O-(sn-Glycero-3-phosphoryl)-choline	HMDB
sn-Glycero-3-phosphorylcholine	HMDB
Α-glycerylphosphorylcholine	HMDB
Glycerophosphocholine	ChEBI

Chemical Formula

C₈H₂₀NO₆P

Average Molecular Weight

257.223

Monoisotopic Molecular Weight

257.102824366

IUPAC Name

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

Traditional Name

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

CAS Registry Number

28319-77-9

SMILES

C[N+](C)(C)CCOP([O-])(=O)OC[C@H](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/t8-/m1/s1

InChI Key

SUHOQUVVVLNYQR-MRVPVSSYSA-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

phosphocholines (CHEBI:16870 )
sn-glycerol 3-phosphates (CHEBI:16870 )

Ontology

Not Available

Non-excretory biofluid

Semen (PMID: 2827914)
Cerebrospinal Fluid (CSF) (PMID: 15465626)
Blood (PMID: 16043031)
Saliva (PMID: 20300169)

Excreta

Cellular substructure

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Retinol Metabolism (PathBank: SMP0087412)
Choline Metabolism (PathBank: SMP0002393)
Lysolipid Incorporation into ER (PathBank: SMP0002425)
Lysolipid Incorporation into ER PC(10:0/10:0) (PathBank: SMP0002512)
Lysolipid Incorporation into ER PC(14:0/14:0) (PathBank: SMP0002513)
Lysolipid Incorporation into ER PC(16:0/16:0) (PathBank: SMP0002514)
Lysolipid Incorporation into ER PC(16:1(9Z)/16:1(9Z)) (PathBank: SMP0002515)
Lysolipid Incorporation into ER PC(16:1(11Z)/16:1(11Z)) (PathBank: SMP0002516)
Lysolipid Incorporation into ER PC(18:0/18:0) (PathBank: SMP0002517)
Lysolipid Incorporation into ER PC(18:1(9Z)/18:1(9Z)) (PathBank: SMP0002518)
Lysolipid Incorporation into ER PC(18:2(9Z,11Z)/18:2(9Z,11Z)) (PathBank: SMP0002519)
Lysolipid Incorporation into ER PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0002520)

Disease pathway

Vitamin A Deficiency (PathBank: SMP0120500)

Role

Industrial application

Pharmaceutical industry

Biomarker

Alzheimer's Disease (MarkerDB: MDB00000045)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	142.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	155.533	30932474
[M+H]+	Not Available	155.725	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000443

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.96 g/L	ALOGPS
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	24.77 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]+	152.032	30932474
DeepCCS	[M-H]-	149.816	30932474
DeepCCS	[M-2H]-	183.278	30932474
DeepCCS	[M+Na]+	157.944	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
Glycerophosphocholine	C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO	2743.9	Standard polar	33892256
Glycerophosphocholine	C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO	1603.0	Standard non polar	33892256
Glycerophosphocholine	C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO	1813.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycerophosphocholine,1TMS,isomer #1	C[N+](C)(C)CCOP(=O)([O-])OC[C@@H](CO)O[Si](C)(C)C	1806.4	Semi standard non polar	33892256
Glycerophosphocholine,1TMS,isomer #2	C[N+](C)(C)CCOP(=O)([O-])OC[C@H](O)CO[Si](C)(C)C	1808.9	Semi standard non polar	33892256
Glycerophosphocholine,2TMS,isomer #1	C[N+](C)(C)CCOP(=O)([O-])OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	1818.7	Semi standard non polar	33892256
Glycerophosphocholine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H](CO)COP(=O)([O-])OCC[N+](C)(C)C	2035.3	Semi standard non polar	33892256
Glycerophosphocholine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O)COP(=O)([O-])OCC[N+](C)(C)C	2042.6	Semi standard non polar	33892256
Glycerophosphocholine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	2318.1	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 - Glycerophosphocholine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-7910000000-79a0f6ec434740d09410	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerophosphocholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerophosphocholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycerophosphocholine 20V, Negative-QTOF	splash10-004i-9310000000-e2633e56c86952054710	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycerophosphocholine 10V, Negative-QTOF	splash10-0a4i-1690000000-53ffc11b39ba8f89f803	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycerophosphocholine 40V, Negative-QTOF	splash10-004i-9000000000-d4d2c5d7e0856e948624	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycerophosphocholine 20V, Negative-QTOF	splash10-004i-9400000000-848201d8ac3bd454c67a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycerophosphocholine 40V, Positive-QTOF	splash10-01w1-9300000000-987e5431e2d611fa5032	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycerophosphocholine 10V, Negative-QTOF	splash10-0a4i-2490000000-efb55f1ddbed9f1a8754	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycerophosphocholine 20V, Positive-QTOF	splash10-0udi-1900000000-df7b0a6ce3c788063f53	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycerophosphocholine 10V, Positive-QTOF	splash10-0zfr-0960000000-7df186ffc569be161b39	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 10V, Positive-QTOF	splash10-052r-9140000000-3347b58fbc5fe0b0a201	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 20V, Positive-QTOF	splash10-0a7r-9210000000-60118aed826a14bb4cb1	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 40V, Positive-QTOF	splash10-0a4r-9000000000-b6ac875e42841f04bcfc	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 10V, Negative-QTOF	splash10-0a4i-0390000000-9adc870a20cd016e3aa2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 20V, Negative-QTOF	splash10-0kor-2920000000-b31eb4ca99ba45d9f931	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 40V, Negative-QTOF	splash10-004i-9100000000-dec05a487d7ae73f1d27	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 10V, Negative-QTOF	splash10-0a4i-0090000000-bd45c4f9a61bbdbbd2d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 20V, Negative-QTOF	splash10-0a4i-3960000000-2d618fc6f1a9c434909c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 40V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 10V, Positive-QTOF	splash10-001i-0960000000-782cafcc84f2e1b58561	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 20V, Positive-QTOF	splash10-001i-0900000000-5fbae562ef71fe1bd552	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycerophosphocholine 40V, Positive-QTOF	splash10-0079-9800000000-00d2deed17b9ac0f5789	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Saliva
Semen
Urine

Tissue Locations

Brain
Kidney
Placenta
Prostate
Spleen

Pathways

Name	SMPDB/PathBank	KEGG
Retinol Metabolism
Vitamin A Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22685041	details
Blood	Detected and Quantified	34.0 +/- 5.0 uM	Infant (0-1 year old)	Both	Normal	16043031	details
Blood	Detected and Quantified	40.0 +/- 4.0 uM	Newborn (0-30 days old)	Both	Normal	16043031	details
Blood	Detected and Quantified	29.0 +/- 5.0 uM	Infant (0-1 year old)	Both	Normal	16043031	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	33.0 +/- 4.0 uM	Adult (>18 years old)	Female	Normal	16043031	details
Breast Milk	Detected and Quantified	471 +/- 161 uM	Adult (>18 years old)	Female	Normal	24027187	details
Breast Milk	Detected and Quantified	362 +/- 70 uM	Adult (>18 years old)	Not Specified	Normal	8839502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	3.94 +/- 1.17 uM	Adult (>18 years old)	Not Specified	Normal	15465626	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	3.9 +/- 1.2 uM	Adult (>18 years old)	Both	Normal	15465626	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	25985090	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27065191	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20300169	details
Saliva	Detected and Quantified	1.05 +/- 0.248 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.38 +/- 0.531 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.84 +/- 0.652 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.98 +/- 1.45 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2.53 +/- 4.35 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	9.82 +/- 6.76 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Semen	Detected and Quantified	2.5 +/- 1.6 uM	Adult (>18 years old)	Both	Normal	2827914	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Kidney cancer	22685041	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.03 +/- 1.52 uM	Elderly (>65 years old)	Not Specified	Vascular dementia	15465626	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.03 (2.51-5.55) uM	Adult (>18 years old)	Both	Vascular dementia	15465626	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	6.9 +/- 3.2 uM	Elderly (>65 years old)	Both	Alzheimer's disease	15465626	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Prosthesis/Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Oral cancer	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Breast cancer	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Pancreatic cancer	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Periodontal diseases	20300169	details

Associated Disorders and Diseases

Disease References

Kidney cancer
Lin L, Huang Z, Gao Y, Chen Y, Hang W, Xing J, Yan X: LC-MS-based serum metabolic profiling for genitourinary cancer classification and cancer type-specific biomarker discovery. Proteomics. 2012 Aug;12(14):2238-46. doi: 10.1002/pmic.201200016. [PubMed:22685041 ]
Multi-infarct dementia
Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. [PubMed:15465626 ]
Alzheimer's disease
Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. [PubMed:15465626 ]
Perillyl alcohol administration for cancer treatment
Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Periodontal disease
Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Prosthesis/Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]

Associated OMIM IDs

104300 (Alzheimer's disease)
260350 (Pancreatic cancer)
170650 (Periodontal disease)

External Links

DrugBank ID

DB04660

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030952

KNApSAcK ID

Not Available

Chemspider ID

571409

KEGG Compound ID

C00670

BioCyc ID

L-1-GLYCERO-PHOSPHORYLCHOLINE

BiGG ID

Not Available

Wikipedia Link

Alpha-GPC

METLIN ID

370

PubChem Compound

657272

PDB ID

Not Available

ChEBI ID

16870

Food Biomarker Ontology

Not Available

VMH ID

G3PC

MarkerDB ID

MDB00000045

Good Scents ID

Not Available

References

Synthesis Reference

Evans, Christopher Thomas; McCague, Raymond; Tyrrell, Nicholas David. Preparation of phospholipid-intermediate glycerophosphocholine by a crystallization process. PCT Int. Appl. (1993), 8 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Satlin A, Bodick N, Offen WW, Renshaw PF: Brain proton magnetic resonance spectroscopy (1H-MRS) in Alzheimer's disease: changes after treatment with xanomeline, an M1 selective cholinergic agonist. Am J Psychiatry. 1997 Oct;154(10):1459-61. [PubMed:9326834 ]
Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. [PubMed:15465626 ]
Theberge J, Al-Semaan Y, Jensen JE, Williamson PC, Neufeld RW, Menon RS, Schaefer B, Densmore M, Drost DJ: Comparative study of proton and phosphorus magnetic resonance spectroscopy in schizophrenia at 4 Tesla. Psychiatry Res. 2004 Nov 15;132(1):33-9. [PubMed:15546701 ]
Miller BL, Lin KM, Djenderedjian A, Tang C, Hill E, Fu P, Nuccio C, Jenden DJ: Changes in red blood cell choline and choline-bound lipids with oral lithium. Experientia. 1990 May 15;46(5):454-6. [PubMed:2347393 ]
Caetano SC, Fonseca M, Olvera RL, Nicoletti M, Hatch JP, Stanley JA, Hunter K, Lafer B, Pliszka SR, Soares JC: Proton spectroscopy study of the left dorsolateral prefrontal cortex in pediatric depressed patients. Neurosci Lett. 2005 Aug 26;384(3):321-6. [PubMed:15936878 ]
Nitsch R, Pittas A, Blusztajn JK, Slack BE, Growdon JH, Wurtman RJ: Alterations of phospholipid metabolites in postmortem brain from patients with Alzheimer's disease. Ann N Y Acad Sci. 1991;640:110-3. [PubMed:1663712 ]
Chap HJ, Moatti JP, Mieusset R, Nieto M, Laneelle G, Bennet PJ, Mansat A, Pontonnier F, Douste-Blazy L: Simple, rapid enzymatic determination of glycerophosphocholine in human seminal plasma. Clin Chem. 1988 Jan;34(1):106-9. [PubMed:2827914 ]
Blusztajn JK, Lopez Gonzalez-Coviella I, Logue M, Growdon JH, Wurtman RJ: Levels of phospholipid catabolic intermediates, glycerophosphocholine and glycerophosphoethanolamine, are elevated in brains of Alzheimer's disease but not of Down's syndrome patients. Brain Res. 1990 Dec 17;536(1-2):240-4. [PubMed:2150771 ]
Mandal PK, McClure RJ, Pettegrew JW: Interactions of Abeta(1-40) with glycerophosphocholine and intact erythrocyte membranes: fluorescence and circular dichroism studies. Neurochem Res. 2004 Dec;29(12):2273-9. [PubMed:15672550 ]
Pomfret EA, daCosta KA, Schurman LL, Zeisel SH: Measurement of choline and choline metabolite concentrations using high-pressure liquid chromatography and gas chromatography-mass spectrometry. Anal Biochem. 1989 Jul;180(1):85-90. [PubMed:2817347 ]
Nitsch RM, Blusztajn JK, Pittas AG, Slack BE, Growdon JH, Wurtman RJ: Evidence for a membrane defect in Alzheimer disease brain. Proc Natl Acad Sci U S A. 1992 Mar 1;89(5):1671-5. [PubMed:1311847 ]
Miller BL, Read S, Tang C, Jenden D: Differences in red blood cell choline and lipid-bound choline between patients with Alzheimer disease and control subjects. Neurobiol Aging. 1991 Jan-Feb;12(1):61-4. [PubMed:2002884 ]
Jensen JE, Drost DJ, Menon RS, Williamson PC: In vivo brain (31)P-MRS: measuring the phospholipid resonances at 4 Tesla from small voxels. NMR Biomed. 2002 Aug;15(5):338-47. [PubMed:12203225 ]
Zhang Q, Southall MD, Mezsick SM, Johnson C, Murphy RC, Konger RL, Travers JB: Epidermal peroxisome proliferator-activated receptor gamma as a target for ultraviolet B radiation. J Biol Chem. 2005 Jan 7;280(1):73-9. Epub 2004 Oct 29. [PubMed:15516334 ]
Fallbrook A, Turenne SD, Mamalias N, Kish SJ, Ross BM: Phosphatidylcholine and phosphatidylethanolamine metabolites may regulate brain phospholipid catabolism via inhibition of lysophospholipase activity. Brain Res. 1999 Jul 10;834(1-2):207-10. [PubMed:10407117 ]
Blank ML, Smith ZL, Fitzgerald V, Snyder F: The CoA-independent transacylase in PAF biosynthesis: tissue distribution and molecular species selectivity. Biochim Biophys Acta. 1995 Feb 9;1254(3):295-301. [PubMed:7857969 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 15 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

Reactions

1-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty acid	details

Enzyme Details

2. Group XV phospholipase A2

General function:: Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:: Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:: PLA2G15
Uniprot ID:: Q8NCC3
Molecular weight:: Not Available

Reactions

1-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty acid	details

Enzyme Details

3. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

Reactions

2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylate	details

Enzyme Details

4. Galactoside-binding soluble lectin 13

General function:: Involved in sugar binding
Specific function:: Has lysophospholipase activity.
Gene Name:: LGALS13
Uniprot ID:: Q9UHV8
Molecular weight:: 16118.44

Reactions

2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylate	details

Enzyme Details

5. Acyl-protein thioesterase 2

General function:: Involved in hydrolase activity
Specific function:: May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:: LYPLA2
Uniprot ID:: O95372
Molecular weight:: 24736.71

Enzyme Details

6. Eosinophil lysophospholipase

General function:: Involved in sugar binding
Specific function:: May have both lysophospholipase and carbohydrate-binding activities.
Gene Name:: CLC
Uniprot ID:: Q05315
Molecular weight:: 16452.785

Reactions

2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylate	details

Enzyme Details

7. 60 kDa lysophospholipase

General function:: Involved in asparaginase activity
Specific function:: Exhibits lysophospholipase, transacylase, PAF acetylhydrolase and asparaginase activities.
Gene Name:: ASPG
Uniprot ID:: Q86U10
Molecular weight:: 60882.4

Reactions

2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylate	details

Enzyme Details

8. Phospholipase B1, membrane-associated

General function:: Involved in hydrolase activity
Specific function:: Membrane-associated phospholipase. Exhibits a calcium-independent broad substrate specificity including phospholipase A2/lysophospholipase activity. Preferential hydrolysis at the sn-2 position of diacylphospholipids and diacyglycerol, whereas it shows no positional specificity toward triacylglycerol. Exhibits also esterase activity toward p-nitrophenyl. May act on the brush border membrane to facilitate the absorption of digested lipids (By similarity).
Gene Name:: PLB1
Uniprot ID:: Q6P1J6
Molecular weight:: 161711.9

Reactions

2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylate	details
1-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty acid	details
2-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty acid	details

Enzyme Details

9. Glycerophosphodiester phosphodiesterase 1

General function:: Involved in glycerophosphodiester phosphodiesterase activity
Specific function:: Has glycerophosphoinositol phosphodiesterase activity. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:: GDE1
Uniprot ID:: Q9NZC3
Molecular weight:: 37718.04

Enzyme Details

10. Calcium-independent phospholipase A2-gamma

General function:: Involved in metabolic process
Specific function:: Calcium-independent phospholipase A2, which catalyzes the hydrolysis of the sn-2 position of glycerophospholipids, PtdSer and to a lower extent PtdCho. Cleaves membrane phospholipids.
Gene Name:: PNPLA8
Uniprot ID:: Q9NP80
Molecular weight:: 88476.085

Reactions

2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylate	details

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Showing metabocard for Glycerophosphocholine (HMDB0000086)

MOL for HMDB0000086 (Glycerophosphocholine)

3D MOL for HMDB0000086 (Glycerophosphocholine)

3D SDF for HMDB0000086 (Glycerophosphocholine)

3D-SDF for HMDB0000086 (Glycerophosphocholine)

PDB for HMDB0000086 (Glycerophosphocholine)

3D PDB for HMDB0000086 (Glycerophosphocholine)

SMILES for HMDB0000086 (Glycerophosphocholine)

INCHI for HMDB0000086 (Glycerophosphocholine)

Structure for HMDB0000086 (Glycerophosphocholine)

3D Structure for HMDB0000086 (Glycerophosphocholine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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