MiMeDB: Showing metabocard for Glycerophosphocholine (MMDBc0000494)

Microbial

Human

Plant

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:02 UTC

Update Date

2024-10-10 01:05:50 UTC

Metabolite ID

MMDBc0000494

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>
MMDBc0000494

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₈H₂₀NO₆P

Average Mass

257.223

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-7910000000-79a0f6ec434740d09410	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9310000000-e2633e56c86952054710	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1690000000-53ffc11b39ba8f89f803	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-d4d2c5d7e0856e948624	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9400000000-848201d8ac3bd454c67a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-01w1-9300000000-987e5431e2d611fa5032	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2490000000-efb55f1ddbed9f1a8754	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1900000000-df7b0a6ce3c788063f53	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0zfr-0960000000-7df186ffc569be161b39	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-9140000000-3347b58fbc5fe0b0a201	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a7r-9210000000-60118aed826a14bb4cb1	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9000000000-b6ac875e42841f04bcfc	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0390000000-9adc870a20cd016e3aa2	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kor-2920000000-b31eb4ca99ba45d9f931	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-dec05a487d7ae73f1d27	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-bd45c4f9a61bbdbbd2d6	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-3960000000-2d618fc6f1a9c434909c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0960000000-782cafcc84f2e1b58561	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-5fbae562ef71fe1bd552	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-9800000000-00d2deed17b9ac0f5789	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Brain
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Kidney
Placenta
Prostate
Saliva
Semen
Spleen
Urine

Tissue Locations

Brain
Kidney
Placenta
Prostate
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191730	Acyl-protein thioesterase 1	Enzyme	O75608	Homo sapiens
MMDBp0191731	Group XV phospholipase A2	Unknown	Q8NCC3	Homo sapiens
MMDBp0191734	Cytosolic phospholipase A2	Unknown	P47712	Homo sapiens
MMDBp0191738	Galactoside-binding soluble lectin 13	Enzyme	Q9UHV8	Homo sapiens
MMDBp0191740	Acyl-protein thioesterase 2	Enzyme	O95372	Homo sapiens
MMDBp0191744	Eosinophil lysophospholipase	Enzyme	Q05315	Homo sapiens
MMDBp0194096	60 kDa lysophospholipase	Enzyme	Q86U10	Homo sapiens
MMDBp0194097	Phospholipase B1, membrane-associated	Unknown	Q6P1J6	Homo sapiens
MMDBp0194171	Glycerophosphodiester phosphodiesterase 1	Unknown	Q9NZC3	Homo sapiens
MMDBp0194716	Calcium-independent phospholipase A2-gamma	Unknown	Q9NP80	Homo sapiens
MMDBp0196265	Neuropathy target esterase	Enzyme	Q8IY17	Homo sapiens
MMDBp0196461	Ectonucleotide pyrophosphatase/phosphodiesterase family member 6	Enzyme	Q6UWR7	Homo sapiens
MMDBp0196823	Glycerophosphocholine phosphodiesterase GPCPD1	Unknown	Q9NPB8
MMDBp0196928	Patatin-like phospholipase domain-containing protein 7	Unknown	Q6ZV29
MMDBp0196994	Lysoplasmalogenase	Unknown	Q8N661

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

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

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019988	PC(16:0/16:0)	Palmitic acid	Lysophospholipase NTE1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0019989	Glycerophosphocholine	Choline	Glycerophosphocholine phosphodiesterase GDE1	Formation of 2'-nucleotide products from 2',3'-cyclic substrates	PathBank	31602464
MMDBr0020060	LysoPC(14:0/0:0)	Glycerophosphocholine	Lysophospholipase NTE1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0020069	LysoPC(16:0/0:0)	Glycerophosphocholine	Lysophospholipase NTE1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0020079	PC(16:1(9Z)/0:0)	Glycerophosphocholine	Lysophospholipase NTE1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0020089	LysoPC(18:0/0:0)	Glycerophosphocholine	Lysophospholipase NTE1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0020095	PC(18:1(9Z)/0:0)	Glycerophosphocholine	Lysophospholipase NTE1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0020104	LysoPC(20:4(5Z,8Z,11Z,14Z))	Glycerophosphocholine	Lysophospholipase NTE1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0024158	LysoPC(10:0)	Glycerophosphocholine	Lysophospholipase NTE1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0024178	LysoPC(16:1(11Z)/0:0)	Glycerophosphocholine	Lysophospholipase NTE1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0024180	LysoPC(18:2(9Z,11Z)/0:0)	Glycerophosphocholine	Lysophospholipase NTE1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0025591	Glycerophosphocholine	CoA	Glycerophosphocholine acyltransferase 1	Acylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	15465626
Multi-infarct dementia		Association	Human Cerebrospinal Fluid (CSF)	HMDB	15465626

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Bacteroidetes	89	Human feces; Human stool; Human ; Human appendix biopsy; Human saliva; Human supragingival plaque; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	332	Human feces; Human pleural fluid plaque; Human ; Human urine; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Pig ; Cattle ; Human stool; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	141	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	109	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human mucosa; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Firmicutes	2	Human feces; Human pleural fluid plaque; Human ; Human urine; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Pig ; Cattle ; Human stool; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	5	Human feces; Human saliva	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	6.9	3.2			uM	Elderly (>65 years old)	Both	Alzheimer's disease	HMDB	15465626
Human Cerebrospinal fluid (csf)	Detected and Quantified	4.03		2.51	5.55	uM	Adult (>18 years old)	Both	Vascular dementia	HMDB	15465626
Human Cerebrospinal fluid (csf)	Detected and Quantified	4.03	1.52			uM	Elderly (>65 years old)	Not Specified	Vascular dementia	HMDB	15465626
Human Semen	Detected and Quantified	2.5	1.6			uM	Adult (>18 years old)	Both	Normal	HMDB	2827914
Human Blood	Detected and Quantified	29.0	5.0			uM	Infant (0-1 year old)	Both	Normal	HMDB	16043031
Human Cerebrospinal fluid (csf)	Detected and Quantified	3.9	1.2			uM	Adult (>18 years old)	Both	Normal	HMDB	15465626
Human Cerebrospinal fluid (csf)	Detected and Quantified	3.94	1.17			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	15465626
Human Blood	Detected and Quantified	33.0	4.0			uM	Adult (>18 years old)	Female	Normal	HMDB	16043031
Human Blood	Detected and Quantified	34.0	5.0			uM	Infant (0-1 year old)	Both	Normal	HMDB	16043031
Human Breast milk	Detected and Quantified	362	70			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	8839502
Human Blood	Detected and Quantified	40.0	4.0			uM	Newborn (0-30 days old)	Both	Normal	HMDB	16043031
Human Breast milk	Detected and Quantified	471	161			uM	Adult (>18 years old)	Female	Normal	HMDB	24027187
Human Saliva	Detected and Quantified	1.05	0.248			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	1.38	0.531			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	1.84	0.652			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	1.98	1.45			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	2.53	4.35			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	9.82	6.76			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	20300169
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22685041
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27065191
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	25985090
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000086

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

CMMC Knowledgebase

Not Available

General References

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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. doi: 10.1111/j.1749-6632.1991.tb00200.x. [PubMed:1663712 ]
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. doi: 10.1016/0197-4580(91)90040-q. [PubMed:2002884 ]
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. doi: 10.1016/0006-8993(90)90030-f. [PubMed:2150771 ]
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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. doi: 10.1002/nbm.776. [PubMed:12203225 ]
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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. doi: 10.1016/j.neulet.2005.04.099. [PubMed:15936878 ]
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 ]
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Showing metabocard for Glycerophosphocholine (MMDBc0000494)

MOL for #<Metabolite:0x0000561537b45008>

3D MOL for #<Metabolite:0x0000561537b45008>

3D SDF for #<Metabolite:0x0000561537b45008>

3D-SDF for #<Metabolite:0x0000561537b45008>

PDB for #<Metabolite:0x0000561537b45008>

3D PDB for #<Metabolite:0x0000561537b45008>

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INCHI for #<Metabolite:0x0000561537b45008>

Structure for #<Metabolite:0x0000561537b45008>

3D Structure for #<Metabolite:0x0000561537b45008>