MiMeDB: Showing metabocard for Citicoline (MMDBc0032916)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:27:16 UTC

Update Date

2024-10-06 18:21:42 UTC

Metabolite ID

MMDBc0032916

Metabolite Identification

Common Name

Citicoline

Description

Citicoline is an essential intermediate in the biosynthetic pathway of structural phospholipids in cell membranes, particularly phosphatidylcholine. Once absorbed, citicoline is widely distributed throughout the body, crosses the blood-brain barrier and reaches the central nervous system (CNS), where it is incorporated into the membrane and microsomal phospholipid fraction. Citicoline activates biosynthesis of structural phospholipids of neuronal membranes, increases brain metabolism, and acts upon the levels of different neurotransmitters. Thus, citicoline has been experimentally shown to increase norepinephrine and dopamine levels in the CNS. Owing to these pharmacological mechanisms, citicoline has a neuroprotective effect in hypoxic and ischemic conditions, decreasing the volume of ischemic lesion, and also improves learning and memory performance in animal models of brain aging. In addition, citicoline has been shown to restore the activity of mitochondrial ATPase and membrane Na+/K+ATPase, to inhibit activation of certain phospholipases, and to accelerate reabsorption of cerebral edema in various experimental models. Citicoline has also been shown to be able to inhibit mechanisms of apoptosis associated to cerebral ischemia and in certain neurodegeneration models, and to potentiate neuroplasticity mechanisms. Citicoline is a safe drug, as shown by the toxicological tests conducted, that has no significant systemic cholinergic effects and is a well tolerated product. (PMID:17171187 ).

Structure

MOL SDF PDB SMILES InChI

      
  Mrv1652309042000222D          

 31 32  0  0  1  0            999 V2000
   16.6783   -8.1241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5032   -8.1241    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7582   -7.3395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0908   -6.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4233   -7.3395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.4031   -6.5138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7088   -6.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9944   -7.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1933   -8.7916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9882   -8.7916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6887   -6.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6887   -5.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4031   -4.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1176   -5.2763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1176   -6.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8381   -6.5173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4031   -4.0400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1694   -7.3395    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.3444   -7.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5193   -7.3395    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.6944   -7.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1694   -6.5154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1694   -8.1653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5193   -6.5154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5193   -8.1653    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.9799   -6.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2654   -7.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5658   -6.9354    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.8613   -6.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1609   -7.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9858   -6.2078    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  3  6  1  1  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  1  9  1  6  0  0  0
  2 10  1  6  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  2  0  0  0  0
 18 23  1  0  0  0  0
 20 24  2  0  0  0  0
 20 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  CHG  2  25  -1  28   1
M  END

      
  Mrv1652309042000222D          

 31 32  0  0  1  0            999 V2000
   16.6783   -8.1241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5032   -8.1241    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7582   -7.3395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0908   -6.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4233   -7.3395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.4031   -6.5138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7088   -6.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9944   -7.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1933   -8.7916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9882   -8.7916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6887   -6.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6887   -5.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4031   -4.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1176   -5.2763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1176   -6.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8381   -6.5173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4031   -4.0400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1694   -7.3395    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.3444   -7.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5193   -7.3395    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.6944   -7.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1694   -6.5154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1694   -8.1653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5193   -6.5154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5193   -8.1653    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.9799   -6.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2654   -7.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5658   -6.9354    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.8613   -6.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1609   -7.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9858   -6.2078    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  3  6  1  1  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  1  9  1  6  0  0  0
  2 10  1  6  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  2  0  0  0  0
 18 23  1  0  0  0  0
 20 24  2  0  0  0  0
 20 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  CHG  2  25  -1  28   1
M  END
> <DATABASE_ID>
MMDBc0032916

> <DATABASE_NAME>
MIME

> <SMILES>
C[N+](C)(C)CCOP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/t9-,11-,12-,13-/m1/s1

> <INCHI_KEY>
RZZPDXZPRHQOCG-OJAKKHQRSA-N

> <FORMULA>
C14H26N4O11P2

> <MOLECULAR_WEIGHT>
488.324

> <EXACT_MASS>
488.107330718

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.53836461969057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]ethyl}trimethylazanium

> <ALOGPS_LOGP>
-1.38

> <JCHEM_LOGP>
-7.108613166138413

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.2590685279371496

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.849943564850884

> <JCHEM_PKA_STRONGEST_BASIC>
-0.032166359698345914

> <JCHEM_POLAR_SURFACE_AREA>
213.49999999999997

> <JCHEM_REFRACTIVITY>
113.58389999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-({[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)ethyl]trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      31.133 -15.165   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.673 -15.165   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.149 -13.700   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      31.903 -12.795   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      30.657 -13.700   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      34.352 -12.159   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      29.323 -12.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      27.990 -13.700   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      30.227 -16.411   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      33.578 -16.411   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      33.019 -11.389   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.019  -9.849   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.352  -9.079   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      35.686  -9.849   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      35.686 -11.389   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      37.031 -12.166   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      34.352  -7.541   0.000  0.00  0.00           N+0
HETATM   18  P   UNK     0      26.450 -13.700   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0      24.910 -13.700   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0      23.369 -13.700   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0      21.830 -13.700   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      26.450 -12.162   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      26.450 -15.242   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      23.369 -12.162   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      23.369 -15.242   0.000  0.00  0.00           O-1
HETATM   26  C   UNK     0      20.496 -12.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.162 -13.700   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      17.856 -12.946   0.000  0.00  0.00           N+1
HETATM   29  C   UNK     0      16.541 -12.186   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.100 -14.255   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.640 -11.588   0.000  0.00  0.00           C+0
CONECT    1    2    5    9                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1    7                                                  
CONECT    6    3   11   15                                                  
CONECT    7    5    8                                                       
CONECT    8    7   18                                                       
CONECT    9    1                                                            
CONECT   10    2                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15                                                            
CONECT   17   13                                                            
CONECT   18    8   19   22   23                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   24   25                                             
CONECT   21   20   26                                                       
CONECT   22   18                                                            
CONECT   23   18                                                            
CONECT   24   20                                                            
CONECT   25   20                                                            
CONECT   26   21   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

Synonyms

Value	Source
[2-CYTIDYLATE-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium	ChEBI
CDP-Colina	ChEBI
Citicolina	ChEBI
Citicolinum	ChEBI
Citidin difosfato de colina	ChEBI
Cyticholine	ChEBI
Cytidindiphosphocholin	ChEBI
Cytidine 5'-(choline diphosphate)	ChEBI
Cytidine 5'-(cholinyl pyrophosphate)	ChEBI
Cytidine 5'-diphosphocholine	ChEBI
Cytidine 5'-diphosphoric choline	ChEBI
Nicholin	Kegg
[2-CYTIDYLic acid-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium	Generator
Cytidine 5'-(choline diphosphoric acid)	Generator
Cytidine 5'-(cholinyl pyrophosphoric acid)	Generator
Audes	HMDB
CDP-Choline	HMDB
Cereb	HMDB
Choline 5'-cytidine diphosphate	HMDB
Choline cytidine diphosphate	HMDB
Citicholine	HMDB
Citidoline	HMDB
Citifar	HMDB
Colite	HMDB
Corenalin	HMDB
Cyscholin	HMDB
Cytidine 5'-diphosphate choline	HMDB
Cytidine 5-diphosphate-trihydrogen	HMDB
Cytidine choline diphosphate	HMDB
Cytidine diphosphate choline	HMDB
Cytidine diphosphate choline ester	HMDB
Cytidine diphosphocholine	HMDB
Cytidine diphosphorylcholine	HMDB
Cytidine-5' diphosphocholine	HMDB
Cytidine-5'-pyrophosphate-hydroxycholine	HMDB
Cytidoline	HMDB
Difosfocin	HMDB
Emicholine F	HMDB
Ensign	HMDB
Haocolin	HMDB
Hornbest	HMDB
Neucolis	HMDB
Nicolin	HMDB
Niticolin	HMDB
p-Hydroxide[2-(trimethylammonio)ethyl] ester	HMDB
Reagin	HMDB
Recofnan	HMDB
Recognan	HMDB
Rexort	HMDB
Sintoclar	HMDB
Somazina	HMDB
Somazine	HMDB
Suncholin	HMDB
Cidifos	HMDB
Diphosphate choline, cytidine	HMDB
Choline, CDP	HMDB
CDP Choline	HMDB
5'-Diphosphocholine, cytidine	HMDB
Cytidine 5' diphosphocholine	HMDB
Choline, cytidine diphosphate	HMDB

Molecular Formula

C₁₄H₂₆N₄O₁₁P₂

Average Mass

488.324

Monoisotopic Mass

488.107330718

IUPAC Name

{2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]ethyl}trimethylazanium

Traditional Name

[2-({[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)ethyl]trimethylazanium

CAS Registry Number

987-78-0

SMILES

C[N+](C)(C)CCOP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O

InChI Identifier

InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/t9-,11-,12-,13-/m1/s1

InChI Key

RZZPDXZPRHQOCG-OJAKKHQRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine ribonucleotides

Direct Parent

Pyrimidine ribonucleoside diphosphates

Alternative Parents

Substituents

Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Phosphocholine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Aminopyrimidine
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Imidolactam
Alkyl phosphate
Tetrahydrofuran
Quaternary ammonium salt
Tetraalkylammonium salt
Heteroaromatic compound
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Oxacycle
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organopnictogen compound
Amine
Alcohol
Organic oxide
Organooxygen compound
Organic oxygen compound
Organic salt
Hydrocarbon derivative
Organic zwitterion
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

phosphocholines (CHEBI:16436 )
nucleotide-(amino alcohol)s (CHEBI:16436 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.99 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-7.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	-0.032	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	213.5 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	113.58 m³·mol⁻¹	ChemAxon
Polarizability	42.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Brain
Erythrocyte
Feces
Intestine
Placenta

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019973	Citicoline	Cytidine monophosphate	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0019976	Citicoline	Cytidine monophosphate	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0019991	Phosphorylcholine	Citicoline	Choline-phosphate cytidylyltransferase	Transfer of a cytidylyl group	PathBank	31602464
MMDBr0019992	DG(16:0/16:0/0:0)	PC(16:0/16:0)	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020061	DG(14:0/14:0/0:0)	Cytidine monophosphate	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020078	DG(10:0/10:0/0:0)	Cytidine monophosphate	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020084	DG(16:1(9Z)/16:1(9Z)/0:0)	Cytidine monophosphate	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020088	Citicoline	Cytidine monophosphate	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020094	DG(18:0/18:0/0:0)	Cytidine monophosphate	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020100	DG(18:1(9Z)/18:1(9Z)/0:0)	Cytidine monophosphate	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020109	DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0)	Cytidine monophosphate	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0024182	Citicoline	Cytidine monophosphate	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0024898	Citicoline	CMP	Cholinephosphotransferase 1	Transfer of phosphate group	RHEA	34755880
MMDBr0024899	Citicoline	CMP	Cholinephosphotransferase 1	Transfer of phosphate group	RHEA	34755880
MMDBr0025584	L-Serine	CMP	Phosphocholine transferase AnkX	Transfer of phosphocholine	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

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

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Brain	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001413

DrugBank ID

DB04290

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16436

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

de la Morena E: Efficacy of CDP-choline in the treatment of senile alterations in memory. Ann N Y Acad Sci. 1991;640:233-6. doi: 10.1111/j.1749-6632.1991.tb00224.x. [PubMed:1776744 ]
Paglia DE, Valentine WN, Nakatani M, Rauth BJ: Selective accumulation of cytosol CDP-choline as an isolated erythrocyte defect in chronic hemolysis. Proc Natl Acad Sci U S A. 1983 May;80(10):3081-5. doi: 10.1073/pnas.80.10.3081. [PubMed:6574471 ]
Weiss GB: Metabolism and actions of CDP-choline as an endogenous compound and administered exogenously as citicoline. Life Sci. 1995;56(9):637-60. doi: 10.1016/0024-3205(94)00427-t. [PubMed:7869846 ]
Alvarez XA, Laredo M, Corzo D, Fernandez-Novoa L, Mouzo R, Perea JE, Daniele D, Cacabelos R: Citicoline improves memory performance in elderly subjects. Methods Find Exp Clin Pharmacol. 1997 Apr;19(3):201-10. [PubMed:9203170 ]
Petersen A, Borregaard N: A family with chronic haemolysis and selective accumulation of erythrocyte CDP-choline. Leukemia. 1997 Aug;11(8):1373-6. doi: 10.1038/sj.leu.2400689. [PubMed:9264395 ]
Porciatti V, Schiavi C, Benedetti P, Baldi A, Campos EC: Cytidine-5'-diphosphocholine improves visual acuity, contrast sensitivity and visually-evoked potentials of amblyopic subjects. Curr Eye Res. 1998 Feb;17(2):141-8. doi: 10.1076/ceyr.17.2.141.5606. [PubMed:9523091 ]
Renshaw PF, Daniels S, Lundahl LH, Rogers V, Lukas SE: Short-term treatment with citicoline (CDP-choline) attenuates some measures of craving in cocaine-dependent subjects: a preliminary report. Psychopharmacology (Berl). 1999 Feb;142(2):132-8. doi: 10.1007/s002130050871. [PubMed:10102764 ]
Alvarez XA, Mouzo R, Pichel V, Perez P, Laredo M, Fernandez-Novoa L, Corzo L, Zas R, Alcaraz M, Secades JJ, Lozano R, Cacabelos R: Double-blind placebo-controlled study with citicoline in APOE genotyped Alzheimer's disease patients. Effects on cognitive performance, brain bioelectrical activity and cerebral perfusion. Methods Find Exp Clin Pharmacol. 1999 Nov;21(9):633-44. [PubMed:10669911 ]
Hayashida K: [Usefulness of SPECT images in helping radiologists understand brain diseases]. Nihon Igaku Hoshasen Gakkai Zasshi. 2001 Apr;61(5):208-14. [PubMed:11398344 ]
Babb SM, Wald LL, Cohen BM, Villafuerte RA, Gruber SA, Yurgelun-Todd DA, Renshaw PF: Chronic citicoline increases phosphodiesters in the brains of healthy older subjects: an in vivo phosphorus magnetic resonance spectroscopy study. Psychopharmacology (Berl). 2002 May;161(3):248-54. doi: 10.1007/s00213-002-1045-y. Epub 2002 Mar 22. [PubMed:12021827 ]
Laurence AD, Layton M, Duley JA, Simmonds HA: Elevated erythrocyte CDP-choline levels associated with beta-thalassaemia in patients with transfusion independent anaemia. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1265-7. doi: 10.1081/NCN-200027535. [PubMed:15571243 ]
Friedman D, Cycowicz YM, Bersick M: The late negative episodic memory effect: the effect of recapitulating study details at test. Brain Res Cogn Brain Res. 2005 May;23(2-3):185-98. doi: 10.1016/j.cogbrainres.2004.10.005. Epub 2004 Nov 21. [PubMed:15820627 ]
Secades JJ, Lorenzo JL: Citicoline: pharmacological and clinical review, 2006 update. Methods Find Exp Clin Pharmacol. 2006 Sep;28 Suppl B:1-56. [PubMed:17171187 ]
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 ]

Showing metabocard for Citicoline (MMDBc0032916)

MOL for #<Metabolite:0x00007f91d56f48e8>

3D MOL for #<Metabolite:0x00007f91d56f48e8>

3D SDF for #<Metabolite:0x00007f91d56f48e8>

3D-SDF for #<Metabolite:0x00007f91d56f48e8>

PDB for #<Metabolite:0x00007f91d56f48e8>

3D PDB for #<Metabolite:0x00007f91d56f48e8>

SMILES for #<Metabolite:0x00007f91d56f48e8>

INCHI for #<Metabolite:0x00007f91d56f48e8>

Structure for #<Metabolite:0x00007f91d56f48e8>

3D Structure for #<Metabolite:0x00007f91d56f48e8>