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Showing NP-Card for Phosphorylcholine (NP0000846)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:47:08 UTC
NP-MRD IDNP0000846
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhosphorylcholine
DescriptionPhosphorylcholine, also known as choline phosphate or CHOP, belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. The phosphate of choline, and the parent compound of the phosphorylcholine family. Phosphorylcholine exists in all living species, ranging from bacteria to humans. Within humans, phosphorylcholine participates in a number of enzymatic reactions. In particular, phosphorylcholine can be converted into choline through its interaction with the enzyme phosphoethanolamine/phosphocholine phosphatase. In addition, phosphorylcholine can be converted into CDP-choline; which is mediated by the enzyme choline-phosphate cytidylyltransferase a. In humans, phosphorylcholine is involved in phospholipid biosynthesis. Outside of the human body, phosphorylcholine has been detected, but not quantified in several different foods, such as barley, pak choy, black radish, saskatoon berries, and acorns.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000846 (Phosphorylcholine)


  Mrv1652309042000242D          

 11 10  0  0  0  0            999 V2000
    1.7605   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  2  0  0  0  0
M  CHG  1   2   1
M  END
Download

3D MOL for NP0000846 (Phosphorylcholine)

HMDB0001565
     RDKit          3D
Phosphorylcholine
 26 25  0  0  0  0  0  0  0  0999 V2000
   -1.8193    1.3312    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4596   -0.0521    0.0962 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6591   -0.8586    0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926   -0.2479   -1.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278   -0.4744    1.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9342   -0.5704    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4815    0.6690    0.0590 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1684    0.4345    0.0858 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.5232    0.0059    1.5009 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4726   -0.8127   -1.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9840    1.8396   -0.3674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    1.6736   -0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3887    1.3457    1.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9155    1.9679    0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152   -0.7848    1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333   -0.5464   -0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4005   -1.9127    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9728    0.0782   -1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502    0.3734   -1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215   -1.3239   -1.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707    0.2634    1.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6626   -1.4547    1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656   -1.2481   -0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5978   -1.0610    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.8566   -1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373    2.2219    0.4115 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
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
 10 25  1  0
 11 26  1  0
M  CHG  1   2   1
M  END
Download

3D SDF for NP0000846 (Phosphorylcholine)


  Mrv1652309042000242D          

 11 10  0  0  0  0            999 V2000
    1.7605   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  2  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
NP0000846

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1

> <INCHI_KEY>
YHHSONZFOIEMCP-UHFFFAOYSA-O

> <FORMULA>
C5H15NO4P

> <MOLECULAR_WEIGHT>
184.1507

> <EXACT_MASS>
184.073869485

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.23194201374944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-(trimethylazaniumyl)ethoxy]phosphonic acid

> <ALOGPS_LOGP>
-2.43

> <JCHEM_LOGP>
-4.7858351941384125

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.179536689159681

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.149843466514803

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
53.066900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ChoP

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000846 (Phosphorylcholine)

HMDB0001565
     RDKit          3D
Phosphorylcholine
 26 25  0  0  0  0  0  0  0  0999 V2000
   -1.8193    1.3312    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4596   -0.0521    0.0962 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6591   -0.8586    0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926   -0.2479   -1.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278   -0.4744    1.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9342   -0.5704    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4815    0.6690    0.0590 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1684    0.4345    0.0858 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.5232    0.0059    1.5009 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4726   -0.8127   -1.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9840    1.8396   -0.3674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    1.6736   -0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3887    1.3457    1.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9155    1.9679    0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152   -0.7848    1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333   -0.5464   -0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4005   -1.9127    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9728    0.0782   -1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502    0.3734   -1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215   -1.3239   -1.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707    0.2634    1.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6626   -1.4547    1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656   -1.2481   -0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5978   -1.0610    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.8566   -1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373    2.2219    0.4115 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
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
 10 25  1  0
 11 26  1  0
M  CHG  1   2   1
M  END
Download

PDB for NP0000846 (Phosphorylcholine)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       3.286  -1.897   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.620  -2.667   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.954  -3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.621  -3.437   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0       9.955  -2.667   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      11.288  -1.897   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      10.725  -4.001   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.185  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for NP0000846 (Phosphorylcholine)

COMPND    HMDB0001565
HETATM    1  C1  UNL     1      -1.819   1.331   0.352  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.460  -0.052   0.096  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -2.659  -0.859   0.315  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.093  -0.248  -1.285  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.428  -0.474   1.001  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.934  -0.570   0.382  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.482   0.669   0.059  1.00  0.00           O  
HETATM    8  P1  UNL     1       3.168   0.435   0.086  1.00  0.00           P  
HETATM    9  O2  UNL     1       3.523   0.006   1.501  1.00  0.00           O  
HETATM   10  O3  UNL     1       3.473  -0.813  -1.027  1.00  0.00           O  
HETATM   11  O4  UNL     1       3.984   1.840  -0.367  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.540   1.674  -0.426  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.389   1.346   1.309  1.00  0.00           H  
HETATM   14  H3  UNL     1      -0.916   1.968   0.399  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.015  -0.785   1.355  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.433  -0.546  -0.430  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.400  -1.913   0.056  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.973   0.078  -1.893  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.250   0.373  -1.617  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.922  -1.324  -1.468  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.371   0.263   1.819  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.663  -1.455   1.478  1.00  0.00           H  
HETATM   23  H12 UNL     1       0.966  -1.248  -0.505  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.598  -1.061   1.138  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.765  -0.857  -1.720  1.00  0.00           H  
HETATM   26  H15 UNL     1       4.437   2.222   0.411  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    5
CONECT    3   15   16   17
CONECT    4   18   19   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   10   25
CONECT   11   26
END
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SMILES for NP0000846 (Phosphorylcholine)

C[N+](C)(C)CCOP(O)(O)=O
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INCHI for NP0000846 (Phosphorylcholine)

InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1
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View in JSmol
Synonyms
ValueSource
Choline phosphateChEBI
CHOPChEBI
N-Trimethyl-2-aminoethylphosphonateChEBI
O-PhosphocholineChEBI
Phosphoryl-cholineChEBI
Trimethyl(2-(phosphonooxy)ethyl)ammoniumChEBI
PhosphocholineKegg
Choline phosphoric acidGenerator
N-Trimethyl-2-aminoethylphosphonic acidGenerator
Chloride, phosphorylcholineHMDB
Phosphate, cholineHMDB
Phosphorylcholine chlorideHMDB
Phosphate chloride, cholineHMDB
Chloride, choline phosphateHMDB
Choline chloride dihydrogen phosphateHMDB
Choline phosphate chlorideHMDB
Chemical FormulaC5H15NO4P
Average Mass184.1507 Da
Monoisotopic Mass184.07387 Da
IUPAC Name[2-(trimethylazaniumyl)ethoxy]phosphonic acid
Traditional NameChoP
CAS Registry Number3616-04-4
SMILES
C[N+](C)(C)CCOP(O)(O)=O
InChI Identifier
InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1
InChI KeyYHHSONZFOIEMCP-UHFFFAOYSA-O
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-09-03View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
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Anthriscus cerefoliumFooDB
Apium graveolensFooDB
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Apium graveolens var. secalinumFooDB
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Brassica oleracea var. italicaFooDB
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Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
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Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
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Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
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CervidaeFooDB
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Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
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Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
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CinnamomumFooDB
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CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
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Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
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ColumbaFooDB
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Corchorus olitoriusFooDB
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CorylusFooDB
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Crocus sativusFooDB
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Cuminum cyminumFooDB
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Cydonia oblongaFooDB
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Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
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Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
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ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
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Fagopyrum esculentumFooDB
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Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
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Glycine maxFooDB
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Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
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Hibiscus sabbariffaFooDB
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Hordeum vulgareFooDB
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Ipomoea aquaticaFooDB
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JuglansFooDB
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Lablab purpureusFooDB
Lactuca sativaFooDB
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Lagopus mutaFooDB
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Lentinus edodesFooDB
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LupinusFooDB
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MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
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Medicago sativaFooDB
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Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
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Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
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MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
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OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
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OryctolagusFooDB
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Pangium eduleFooDB
Panicum miliaceumFooDB
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Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
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Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
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Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentPhosphocholines
Alternative Parents
Substituents
  • Phosphocholine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Tetraalkylammonium salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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 Solubility4.36 g/LALOGPS
logP-2.4ALOGPS
logP-4.8ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.07 m³·mol⁻¹ChemAxon
Polarizability17.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001565
DrugBank IDDB03945
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031111
KNApSAcK IDC00007299
Chemspider ID989
KEGG Compound IDC00588
BioCyc IDPHOSPHORYL-CHOLINE
BiGG ID48308
Wikipedia LinkPhosphorylcholine
METLIN ID6326
PubChem Compound1014
PDB IDNot Available
ChEBI ID18132
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. Katz-Brull R, Margalit R, Degani H: Differential routing of choline in implanted breast cancer and normal organs. Magn Reson Med. 2001 Jul;46(1):31-8. [PubMed:11443708 ]
  5. Stoll AL, Renshaw PF, De Micheli E, Wurtman R, Pillay SS, Cohen BM: Choline ingestion increases the resonance of choline-containing compounds in human brain: an in vivo proton magnetic resonance study. Biol Psychiatry. 1995 Feb 1;37(3):170-4. [PubMed:7727625 ]
  6. Nordenstam G, Andersson B, Briles D, Brooks JW Jr, Oden A, Svanborg A, Eden CS: High anti-phosphorylcholine antibody levels and mortality associated with pneumonia. Scand J Infect Dis. 1990;22(2):187-95. [PubMed:2356441 ]
  7. Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5. [PubMed:25935 ]
  8. Toth M, Gimes G: Phosphocholine transferase is more efficient than diacylglycerol kinase as possible attenuator of diacylglycerol signals in primordial human placenta. Acta Physiol Hung. 1993;81(4):341-54. [PubMed:8067249 ]
  9. Kanekura T, Nagata Y, Miyoshi H, Ishihara K, Nakabayashi N, Kanzaki T: Beneficial effects of synthetic phospholipid polymer, poly(2-methacryloyloxyethyl phosphorylcholine-co-n-butyl methacrylate), on stratum corneum function. Clin Exp Dermatol. 2002 May;27(3):230-4. [PubMed:12072015 ]
  10. Ueda H, Watanabe J, Konno T, Takai M, Saito A, Ishihara K: Asymmetrically functional surface properties on biocompatible phospholipid polymer membrane for bioartificial kidney. J Biomed Mater Res A. 2006 Apr;77(1):19-27. [PubMed:16345080 ]
  11. Kanfer JN, Pettegrew JW, Moossy J, McCartney DG: Alterations of selected enzymes of phospholipid metabolism in Alzheimer's disease brain tissue as compared to non-Alzheimer's demented controls. Neurochem Res. 1993 Mar;18(3):331-4. [PubMed:8386814 ]
  12. Hartwich J, Dembinska-Kiec A, Gruca A, Motyka M, Partyka L, Skrzeczynska J, Bzowska M, Pryjma J, Huber J, Leitinger N, Schmitz G: Regulation of platelet adhesion by oxidized lipoproteins and oxidized phospholipids. Platelets. 2002 May;13(3):141-51. [PubMed:12180496 ]
  13. Nakabayashi N, Iwasaki Y: Copolymers of 2-methacryloyloxyethyl phosphorylcholine (MPC) as biomaterials. Biomed Mater Eng. 2004;14(4):345-54. [PubMed:15472384 ]
  14. Jansen SM, Groener JE, Bax W, Suter A, Saftig P, Somerharju P, Poorthuis BJ: Biosynthesis of phosphatidylcholine from a phosphocholine precursor pool derived from the late endosomal/lysosomal degradation of sphingomyelin. J Biol Chem. 2001 Jun 1;276(22):18722-7. Epub 2001 Mar 16. [PubMed:11376003 ]
  15. Iwasaki Y, Yamasaki A, Ishihara K: Platelet compatible blood filtration fabrics using a phosphorylcholine polymer having high surface mobility. Biomaterials. 2003 Sep;24(20):3599-604. [PubMed:12809789 ]
  16. Tomassen SF, Fekkes D, de Jonge HR, Tilly BC: Osmotic swelling-provoked release of organic osmolytes in human intestinal epithelial cells. Am J Physiol Cell Physiol. 2004 Jun;286(6):C1417-22. Epub 2004 Feb 11. [PubMed:14960416 ]
  17. Dagnelie PC, Bell JD, Cox IJ, Menon DK, Sargentoni J, Coutts GA, Williams SC: Effects of fish oil on phospholipid metabolism in human and rat liver studied by 31P NMR spectroscopy in vivo and in vitro. NMR Biomed. 1993 Mar-Apr;6(2):157-62. [PubMed:8499247 ]
  18. Bell JD, Cox IJ, Sargentoni J, Peden CJ, Menon DK, Foster CS, Watanapa P, Iles RA, Urenjak J: A 31P and 1H-NMR investigation in vitro of normal and abnormal human liver. Biochim Biophys Acta. 1993 Nov 25;1225(1):71-7. [PubMed:8241291 ]
  19. Zhu X, Song J, Mar MH, Edwards LJ, Zeisel SH: Phosphatidylethanolamine N-methyltransferase (PEMT) knockout mice have hepatic steatosis and abnormal hepatic choline metabolite concentrations despite ingesting a recommended dietary intake of choline. Biochem J. 2003 Mar 15;370(Pt 3):987-93. [PubMed:12466019 ]
  20. Planchart S, Botto C, Alarcon de Noya B, Bonifacino R, Vivas L, Spencer L, Vivas S: Evaluation of the double diffusion, enzyme immunoassay and immunoblotting techniques, for the diagnosis of human hydatid disease in tropical areas. Rev Inst Med Trop Sao Paulo. 1994 May-Jun;36(3):205-10. [PubMed:7855483 ]
  21. Lochnit G, Dennis RD, Geyer R: Phosphorylcholine substituents in nematodes: structures, occurrence and biological implications. Biol Chem. 2000 Sep-Oct;381(9-10):839-47. [PubMed:11076016 ]