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Showing metabocard for Glycerylphosphorylethanolamine (HMDB0000114)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (7) Show 7 proteinsXML
enzymes (7) Show 7 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:57:28 UTC
HMDB IDHMDB0000114
Secondary Accession Numbers
  • HMDB00114
Metabolite Identification
Common NameGlycerylphosphorylethanolamine
Descriptionsn-glycero-3-phosphoethanolamine belongs to the class of organic compounds known as glycerophosphoethanolamines. These are glycerolipids characterized by an ethanolamine ester of glycerophosphoric acid. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. sn-glycero-3-phosphoethanolamine is a very strong basic compound (based on its pKa).
Structure
Data?1582752112
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000114 (Glycerylphosphorylethanolamine)


  Mrv1652308071917402D          

 13 12  0  0  0  0            999 V2000
 9992.4480 9992.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1619 9993.0426    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8772 9992.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5926 9993.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3059 9992.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0212 9993.0426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.7511 9993.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5763 9993.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7335 9993.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0188 9992.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3042 9993.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5897 9992.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0188 9991.8050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000114 (Glycerylphosphorylethanolamine)

     RDKit          3D

 27 26  0  0  0  0  0  0  0  0999 V2000
    4.2697   -0.7412    0.8290 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    0.2137   -0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9620    0.4487   -0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520    0.9746    0.3304 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6466    1.2889   -0.0511 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.4966    1.7386   -1.5003 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0839    2.5062    1.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.1382    0.1583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739    0.2174    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4736   -0.9871    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3776   -1.8763   -0.5992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8910   -0.4523    0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7938   -1.4627    0.8809 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -1.6602    0.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215   -0.4375    1.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406   -0.1944   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8131    1.1343    0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9123    1.1390   -1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4584   -0.5074   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8471    2.7810    0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7778    0.9000    1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513    0.7263   -0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1572   -1.4932    1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4412   -2.8228   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8477    0.2760    1.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1635    0.1532   -0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3471   -1.7246    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  7 20  1  0
  9 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
M  END
Download

3D SDF for HMDB0000114 (Glycerylphosphorylethanolamine)


  Mrv1652308071917402D          

 13 12  0  0  0  0            999 V2000
 9992.4480 9992.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1619 9993.0426    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8772 9992.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5926 9993.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3059 9992.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0212 9993.0426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.7511 9993.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5763 9993.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7335 9993.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0188 9992.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3042 9993.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5897 9992.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0188 9991.8050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000114

> <DATABASE_NAME>
hmdb

> <SMILES>
NCCOP(O)(=O)OCC(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C5H14NO6P/c6-1-2-11-13(9,10)12-4-5(8)3-7/h5,7-8H,1-4,6H2,(H,9,10)

> <INCHI_KEY>
JZNWSCPGTDBMEW-UHFFFAOYSA-N

> <FORMULA>
C5H14NO6P

> <MOLECULAR_WEIGHT>
215.1415

> <EXACT_MASS>
215.055873697

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.073348670448354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-aminoethoxy)(2,3-dihydroxypropoxy)phosphinic acid

> <ALOGPS_LOGP>
-2.31

> <JCHEM_LOGP>
-3.3911924765119976

> <ALOGPS_LOGS>
-0.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.641343579378521

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8690882900003905

> <JCHEM_PKA_STRONGEST_BASIC>
9.999830157645516

> <JCHEM_POLAR_SURFACE_AREA>
122.24000000000001

> <JCHEM_REFRACTIVITY>
43.8211

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.65e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycerophosphorylethanolamine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000114 (Glycerylphosphorylethanolamine)

https://cactus.nci.nih.gov/chemical/structure/NCCOP(O)(=O)OCC(O)CO/file?forma...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:26})
 27 26  0  0  0  0  0  0  0  0999 V2000
    4.2060    2.0629    0.5787 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3908    0.9978   -0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4737   -0.1795   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1098    0.2266   -0.2089 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701   -0.7621    0.0703 P   0  0  1  0  0  0  0  0  0  0  0  0
    0.8770   -1.9511   -1.0150 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920   -1.3342    1.4298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089    0.0610   -0.0440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840   -0.5119    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8764    0.5384    0.0417 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9342    0.8950   -1.3409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263   -0.0352    0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2264    0.9818    0.3906 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8012    2.8525    0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2383    2.3439    0.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    1.3790   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4287    0.6651   -0.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6742   -1.0038   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6603   -0.5038    0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8002   -1.6487   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9635   -1.3602   -0.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -0.8489    1.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6489    1.4234    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1330    0.1545   -1.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4955   -0.8660   -0.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1559   -0.3890    1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1097    0.6881    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  2 16  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  1  0  0  0
  5  8  1  0  0  0  0
  6 20  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 23  1  1  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 25  1  0  0  0  0
 12 26  1  0  0  0  0
 13 27  1  0  0  0  0
M  END
$$$$
Download

PDB for HMDB0000114 (Glycerylphosphorylethanolamine)

HEADER    PROTEIN                                 07-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-AUG-19         0                                  
HETATM    1  O   UNK     0    8652.5708652.910   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0    8653.9028653.680   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0    8655.2388652.910   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8656.5738653.680   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8657.9048652.910   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8659.2408653.680   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0    8653.1358655.011   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8654.6768655.011   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8651.2368653.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8649.9028652.910   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8648.5688653.680   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8647.2348652.910   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8649.9028651.369   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3    7    8                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    2                                                            
CONECT    8    2                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
Download

3D PDB for HMDB0000114 (Glycerylphosphorylethanolamine)

COMPND    https://cactus.nci.nih.gov/chemical/structure/NCCOP(O)(=O)OCC(O)CO/file?forma... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  N   UNL     1       4.206   2.063   0.579  1.00  0.00           N  
HETATM    2  C   UNL     1       4.391   0.998  -0.416  1.00  0.00           C  
HETATM    3  C   UNL     1       3.474  -0.179  -0.079  1.00  0.00           C  
HETATM    4  O   UNL     1       2.110   0.227  -0.209  1.00  0.00           O  
HETATM    5  P   UNL     1       0.870  -0.762   0.070  1.00  0.00           P  
HETATM    6  O   UNL     1       0.877  -1.951  -1.015  1.00  0.00           O  
HETATM    7  O   UNL     1       0.992  -1.334   1.430  1.00  0.00           O  
HETATM    8  O   UNL     1      -0.509   0.061  -0.044  1.00  0.00           O  
HETATM    9  C   UNL     1      -1.784  -0.512   0.252  1.00  0.00           C  
HETATM   10  C   UNL     1      -2.876   0.538   0.042  1.00  0.00           C  
HETATM   11  O   UNL     1      -2.934   0.895  -1.341  1.00  0.00           O  
HETATM   12  C   UNL     1      -4.226  -0.035   0.477  1.00  0.00           C  
HETATM   13  O   UNL     1      -5.226   0.982   0.391  1.00  0.00           O  
HETATM   14  H   UNL     1       4.801   2.853   0.378  1.00  0.00           H  
HETATM   15  H   UNL     1       3.238   2.344   0.632  1.00  0.00           H  
HETATM   16  H   UNL     1       4.143   1.379  -1.407  1.00  0.00           H  
HETATM   17  H   UNL     1       5.429   0.665  -0.404  1.00  0.00           H  
HETATM   18  H   UNL     1       3.674  -1.004  -0.763  1.00  0.00           H  
HETATM   19  H   UNL     1       3.660  -0.504   0.945  1.00  0.00           H  
HETATM   20  H   UNL     1       0.800  -1.649  -1.930  1.00  0.00           H  
HETATM   21  H   UNL     1      -1.964  -1.360  -0.408  1.00  0.00           H  
HETATM   22  H   UNL     1      -1.799  -0.849   1.289  1.00  0.00           H  
HETATM   23  H   UNL     1      -2.649   1.423   0.636  1.00  0.00           H  
HETATM   24  H   UNL     1      -3.133   0.154  -1.930  1.00  0.00           H  
HETATM   25  H   UNL     1      -4.495  -0.866  -0.175  1.00  0.00           H  
HETATM   26  H   UNL     1      -4.156  -0.389   1.506  1.00  0.00           H  
HETATM   27  H   UNL     1      -6.110   0.688   0.652  1.00  0.00           H  
CONECT    1    2   14   15                                            
CONECT    2    1    3   16   17                                       
CONECT    3    2    4   18   19                                       
CONECT    4    3    5                                                 
CONECT    5    4    6    7    7                                       
CONECT    5    8                                                      
CONECT    6    5   20                                                 
CONECT    7    5    5                                                 
CONECT    8    5    9                                                 
CONECT    9    8   10   21   22                                       
CONECT   10    9   11   12   23                                       
CONECT   11   10   24                                                 
CONECT   12   10   13   25   26                                       
CONECT   13   12   27                                                 
CONECT   14    1                                                      
CONECT   15    1                                                      
CONECT   16    2                                                      
CONECT   17    2                                                      
CONECT   18    3                                                      
CONECT   19    3                                                      
CONECT   20    6                                                      
CONECT   21    9                                                      
CONECT   22    9                                                      
CONECT   23   10                                                      
CONECT   24   11                                                      
CONECT   25   12                                                      
CONECT   26   12                                                      
CONECT   27   13                                                      
MASTER        0    0    0    0    0    0    0    0   27    0   27    0
END
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SMILES for HMDB0000114 (Glycerylphosphorylethanolamine)

NCCOP(O)(=O)OCC(O)CO
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INCHI for HMDB0000114 (Glycerylphosphorylethanolamine)

InChI=1S/C5H14NO6P/c6-1-2-11-13(9,10)12-4-5(8)3-7/h5,7-8H,1-4,6H2,(H,9,10)
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Synonyms
ValueSource
GlycerophosphorylethanolamineChEBI
sn-Glycerol-3-phosphoethanolamineChEBI
GlycerophosphoethanolamineMeSH
GlycerylphosphorylethanolamineMeSH
GPEAHMDB
Glycerol 3-phosphoethanolamineHMDB
Glycerol 3-phosphorylethanolamineHMDB
Glycerol phosphorylethanolamineHMDB
Glyceryl-3-phosphorylethanolamineHMDB
alpha-GlycerophosphorylethanolamineHMDB
sn-Glycero-3-phosphoethanolamineHMDB
α-GlycerophosphorylethanolamineHMDB
Chemical FormulaC5H14NO6P
Average Molecular Weight215.1415
Monoisotopic Molecular Weight215.055873697
IUPAC Name(2-aminoethoxy)(2,3-dihydroxypropoxy)phosphinic acid
Traditional Nameglycerophosphorylethanolamine
CAS Registry Number1190-00-7
SMILES
NCCOP(O)(=O)OCC(O)CO
InChI Identifier
InChI=1S/C5H14NO6P/c6-1-2-11-13(9,10)12-4-5(8)3-7/h5,7-8H,1-4,6H2,(H,9,10)
InChI KeyJZNWSCPGTDBMEW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycerophosphoethanolamines. These are glycerolipids characterized by an ethanolamine ester of glycerophosphoric acid. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentGlycerophosphoethanolamines
Alternative Parents
Substituents
  • Sn-glycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Secondary alcohol
  • 1,2-diol
  • Primary amine
  • Primary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility29.2 g/LALOGPS
logP-2.3ALOGPS
logP-3.4ChemAxon
logS-0.77ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area122.24 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity43.82 m³·mol⁻¹ChemAxon
Polarizability19.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gwf-5900000000-55796a83071cae1bff8b2016-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03ea-8900000000-fb5862be261c9e56b1c12021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9110000000-687d834f521d42c7e36c2015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-f3f7dcb5cdd10c48a24a2015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-750b47541e6949c8a75f2015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2950000000-9e71c620f3a5db1afe862015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9700000000-823f904dfffc25785d542015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fdc87551301ed4f6a0092015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0h00-9460000000-32cd47677e60fcdcf1012021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-30cffc727549756341602021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ca30e71e114ea66730882021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9710000000-e0cffde8c86999d55b582021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-9100000000-3885584fdb3534a0f84e2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-36cf29cb44eeb3400dfa2021-09-09View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue Locations
  • Brain
  • Liver
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021895
KNApSAcK IDNot Available
Chemspider ID110410
KEGG Compound IDC01233
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5151
PubChem Compound123874
PDB IDNot Available
ChEBI ID52330
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceTronconi, Giovanni. Process for the chromatographic isolation of 1-(a)-glycerylphosphorylcholine and of L-(a)-glycerylphosphorylethanolamine. PCT Int. Appl. (1990), 18 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kish SJ, Robitaille Y, Ball M, Gilbert J, Deck JH, Chang LJ, Schut L: Glycerophosphoethanolamine concentration is elevated in brain of patients with dominantly inherited olivopontocerebellar atrophy. Neurosci Lett. 1990 Dec 11;120(2):209-11. [PubMed:2293106 ]
  2. Perry TL, Hansen S, Gandham SS: Postmortem changes of amino compounds in human and rat brain. J Neurochem. 1981 Feb;36(2):406-10. [PubMed:7463068 ]
  3. 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 ]
  4. 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 ]
  5. Nelson C, Moffat B, Jacobsen N, Henzel WJ, Stults JT, King KL, McMurtrey A, Vandlen R, Spencer SA: Glycerophosphorylethanolamine (GPEA) identified as an hepatocyte growth stimulator in liver extracts. Exp Cell Res. 1996 Nov 25;229(1):20-6. [PubMed:8940245 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]

Enzymes

Enzyme Details
1. Acyl-protein thioesterase 1
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
LYPLA1
Uniprot ID:
O75608
Molecular weight:
24669.355
Enzyme Details
2. 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
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
Enzyme Details
4. 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
5. 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
Enzyme Details
6. 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
7. MHC class I antigen
General function:
Involved in immune response
Specific function:
Not Available
Gene Name:
HLA-B
Uniprot ID:
Q95372
Molecular weight:
21058.9