Showing metabocard for Phosphorylcholine (MMDBc0000391)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:36:44 UTC
Update Date2024-10-15 17:48:40 UTC
Metabolite IDMMDBc0000391
Metabolite 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005645c9e8dea0>


  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 #<Metabolite:0x00005645c9e8dea0>

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 #<Metabolite:0x00005645c9e8dea0>


  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>
MMDBc0000391

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00005645c9e8dea0>

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
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PDB for #<Metabolite:0x00005645c9e8dea0>

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 #<Metabolite:0x00005645c9e8dea0>

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 #<Metabolite:0x00005645c9e8dea0>

C[N+](C)(C)CCOP(O)(O)=O
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INCHI for #<Metabolite:0x00005645c9e8dea0>

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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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
Molecular FormulaC5H15NO4P
Average Mass184.1507
Monoisotopic Mass184.073869485
IUPAC Name[2-(trimethylazaniumyl)ethoxy]phosphonic acid
Traditional NameChoP
CAS Registry NumberNot Available
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