NP-MRD: Showing NP-Card for Glycerophosphocholine (NP0000619)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2022-08-02 16:15:23 UTC

NP-MRD ID

NP0000619

Secondary Accession Numbers

None

Natural Product 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>
NP0000619

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

257.2230 Da

Monoisotopic Mass

257.10282 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-08-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ailuropoda melanoleuca	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Castanea sativa	Plant	KNApSAcK
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Paraburkholderia phymatum	-	KNApSAcK
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	142.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-5.398 (est)	The Good Scents Company Information System

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

External Links

HMDB ID

HMDB0000086

DrugBank ID

DB04660

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

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

Good Scents ID

rw1661511

References

General References

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 ]
Du P, Wang G, Hu T, Li H, An Z: Integration Analysis of Pharmacokinetics and Metabolomics to Predict Metabolic Phenotype and Drug Exposure of Remdesivir. Front Pharmacol. 2022 Jan 5;12:779135. doi: 10.3389/fphar.2021.779135. eCollection 2021. [PubMed:35069201 ]

Showing NP-Card for Glycerophosphocholine (NP0000619)

MOL for NP0000619 (Glycerophosphocholine)

3D MOL for NP0000619 (Glycerophosphocholine)

3D SDF for NP0000619 (Glycerophosphocholine)

3D-SDF for NP0000619 (Glycerophosphocholine)

PDB for NP0000619 (Glycerophosphocholine)

3D PDB for NP0000619 (Glycerophosphocholine)

SMILES for NP0000619 (Glycerophosphocholine)

INCHI for NP0000619 (Glycerophosphocholine)

Structure for NP0000619 (Glycerophosphocholine)

3D Structure for NP0000619 (Glycerophosphocholine)