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

2024-04-30 19:54:58 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-7649200000-859d046834f1fbd3d535	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00yi-7947012000-9f83d07fb5a59a93e770	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0001900000-a9f38ff6b185b45f04b3	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03e9-0590000000-b021677d064d65810ee0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-0900000000-7570bbb10dd9fa288442	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-0000900000-8b411373962b073b4d22	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-000i-0001900000-6e7cc437ad79eb13c032	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-01qi-1932200000-9c3803cefdd9c6285a7c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-6505900000-3d534aab6e40915c3642	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-6505900000-fc13e5ad403e7faf8218	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-6505900000-3d534aab6e40915c3642	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-6505900000-fc13e5ad403e7faf8218	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0000900000-8b411373962b073b4d22	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0001900000-6e7cc437ad79eb13c032	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01qi-1932200000-4a7ae92c6e127d2ce453	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-2900100000-0ce672506aae2d1e5eef	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3900000000-c05f3e5b6782e32eeebb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-8900000000-17466c845e643c77969b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01p9-0501900000-be567596c9f980cea8c2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-3904100000-4c2e6535887540a12444	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fu-9600000000-e42f82159eabb4ec781a	2017-09-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000467	Phosphorylcholine	Citicoline	Phosphate cytidylyltransferase 1, choline, alpha	Choline Phosphate Cytididyltransferase	VMH; KEGG	30371894
MMDBr0002868	Citicoline	Citicoline	Not Available	Vesicular Transport	VMH	11306702 11494055 64250 9923963
MMDBr0009372	Citicoline	Cytidine monophosphate	Not Available	Ceramide Cholinephosphotransferase	VMH	30371894
MMDBr0013827	Cytidine triphosphate	Citicoline	Probable choline-phosphate cytidylyltransferase	Transfer of a cytidylyl group	RHEA	34755880
MMDBr0013828	Cytidine triphosphate	Citicoline	Choline-phosphate cytidylyltransferase	Transfer of a cytidylyl group	RHEA	34755880
MMDBr0016052	1,2-dioleoylglycerol	PC(18:1(9Z)/18:1(9Z))	Choline/ethanolaminephosphotransferase 1	Transfer of phosphate group	RHEA	34755880
MMDBr0016053	1,2-dioleoylglycerol	PC(18:1(9Z)/18:1(9Z))	Choline/ethanolaminephosphotransferase 1	Transfer of phosphate group	RHEA	34755880
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	Hydrogen Ion	Pyrophosphate	Choline-phosphate cytidylyltransferase	Transfer of a cytidylyl group	PathBank	31602464
MMDBr0019992	DG(16:0/16:0/0:0)	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020061	DG(14:0/14:0/0:0)	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020078	DG(10:0/10:0/0:0)	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020084	DG(16:1(9Z)/16:1(9Z)/0:0)	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020088	Citicoline	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020094	DG(18:0/18:0/0:0)	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020100	DG(18:1(9Z)/18:1(9Z)/0:0)	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0020109	DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0)	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0024182	Citicoline	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	PathBank	31602464
MMDBr0024898	Citicoline	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	RHEA	34755880
MMDBr0024899	Citicoline	Hydrogen Ion	Cholinephosphotransferase 1	Transfer of phosphate group	RHEA	34755880
MMDBr0025584	L-Serine	Hydrogen Ion	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

Source Type	Species	Data Source	Reference
Animal	Haliotis	FooDB	31437929
Animal	Strombidae	FooDB	31437929
Animal	Clupea harengus harengus	FooDB	31437929
Animal	Undaria pinnatifida	FooDB	31437929
Animal	Peprilus triacanthus	FooDB	31437929
Animal	Rhodophyta	FooDB	31437929
Animal	Myoxocephalus	FooDB	31437929
Animal	Eucheuma	FooDB	31437929
Animal	Saccharina japonica	FooDB	31437929
Animal	Spirulina	FooDB	31437929
Animal	Lota lota	FooDB	31437929
Animal	Porphyra umbilicalis	FooDB	31437929
Animal	Chondrus crispus	FooDB	31437929
Animal	Laminaria	FooDB	31437929
Plant	Castanea crenata	FooDB	31437929
Plant	Litchi chinensis	FooDB	31437929
Plant	Juglans regia	FooDB	31437929
Plant	Quercus	FooDB	31437929
Plant	Trigonella foenum-graecum	FooDB	31437929
Plant	Vaccinium angustifolium	FooDB	31437929
Plant	Physalis	FooDB	31437929
Plant	Malpighia emarginata	FooDB	31437929
Plant	Brassica oleracea var. sabauda	FooDB	31437929
Plant	Brassica napus	FooDB	31437929
Plant	Thelesperma	FooDB	31437929
Plant	Asparagus officinalis	FooDB	31437929
Plant	Chamerion angustifolium	FooDB	31437929
Plant	Levisticum officinale	FooDB	31437929
Plant	Pimpinella anisum	FooDB	31437929
Plant	Citrus aurantiifolia	FooDB	31437929
Plant	Lactuca sativa	FooDB	31437929
Plant	Vaccinium elliottii	FooDB	31437929
Plant	Artemisia dracunculus	FooDB	31437929
Plant	Matricaria recutita	FooDB	31437929
Plant	Ziziphus zizyphus	FooDB	31437929
Plant	Dimocarpus longan	FooDB	31437929
Plant	Eragrostis tef	FooDB	31437929
Plant	Salvia hispanica	FooDB	31437929
Plant	Pistacia vera	FooDB	31437929
Plant	Malus pumila	FooDB	31437929
Plant	Pangium edule	FooDB	31437929
Plant	Cynara cardunculus	FooDB	31437929
Plant	Vitellaria paradoxa	FooDB	31437929
Plant	Allium	FooDB	31437929
Plant	Brassica oleracea var. viridis	FooDB	31437929
Plant	Punica granatum	FooDB	31437929
Plant		FooDB	31437929
Plant	Agave	FooDB	31437929
Plant	Diospyros	FooDB	31437929
Plant	Hedysarum alpinum	FooDB	31437929
Plant	Gossypium	FooDB	31437929
Plant	Vigna aconitifolia	FooDB	31437929
Plant	Amaranthus	FooDB	31437929
Plant	Beta vulgaris	FooDB	31437929
Plant	Mammea americana	FooDB	31437929
Plant	Annona squamosa	FooDB	31437929
Plant	Brassica alboglabra	FooDB	31437929
Plant	Vitis	FooDB	31437929
Plant	Cucumis sativus	FooDB	31437929
Plant	Apium graveolens var. dulce	FooDB	31437929
Plant	Xanthosoma sagittifolium	FooDB	31437929
Plant	Basella alba	FooDB	31437929
Plant	Carya illinoinensis	FooDB	31437929
Plant	Citrus latifolia	FooDB	31437929
Plant	Capsicum baccatum var. baccatum	FooDB	31437929
Plant	Byrsonima crassifolia	FooDB	31437929
Plant	Ribes rubrum	FooDB	31437929
Plant	Cinnamomum aromaticum	FooDB	31437929
Plant	Capsicum pubescens	FooDB	31437929
Plant	Crateva religiosa	FooDB	31437929
Plant	Brassica rapa var. chinensis	FooDB	31437929
Plant		FooDB	31437929
Plant	Portulaca oleracea	FooDB	31437929
Plant	Ipomoea batatas	FooDB	31437929
Plant	Mentha arvensis	FooDB	31437929
Plant	Vitis aestivalis	FooDB	31437929
Plant	Eugenia javanica	FooDB	31437929
Plant	Pastinaca sativa	FooDB	31437929
Plant	Cucurbita maxima	FooDB	31437929
Plant	Chenopodium album	FooDB	31437929
Plant	Psophocarpus tetragonolobus	FooDB	31437929
Plant	Vaccinium stamineum	FooDB	31437929
Plant	Solanum lycopersicum var. cerasiforme	FooDB	31437929
Plant	Allium ampeloprasum	FooDB	31437929
Plant	Brassica oleracea	FooDB	31437929
Plant	Sechium edule	FooDB	31437929
Plant	Lactuca sativa l. var. longifolia	FooDB	31437929
Plant	Grataegosorbus mitschurinii	FooDB	31437929
Plant	Diospyros virginiana	FooDB	31437929
Plant	Origanum x majoricum	FooDB	31437929
Plant	Rubus x loganobaccus	FooDB	31437929
Plant	Taraxacum officinale	FooDB	31437929
Plant	Tragopogon porrifolius	FooDB	31437929
Plant	Rumex	FooDB	31437929
Plant	Allium ascalonicum	FooDB	31437929
Plant	Curcuma longa	FooDB	31437929
Plant	Ananas comosus	FooDB	31437929
Plant	Rubus chamaemorus	FooDB	31437929
Plant	Persea americana	FooDB	31437929
Plant	Elettaria cardamomum	FooDB	31437929
Plant	Citrullus lanatus var. fistulosus	FooDB	31437929
Plant	Amelanchier alnifolia	FooDB	31437929
Plant	Eugenia uniflora	FooDB	31437929
Plant	Annona reticulata	FooDB	31437929
Plant	Cichorium intybus	FooDB	31437929
Plant	Sesbania bispinosa	FooDB	31437929
Plant	Brassica oleracea var. botrytis	FooDB	31437929
Plant	Chenopodium quinoa	FooDB	31437929
Plant	Cucumis melo	FooDB	31437929
Plant	Ribes x nidigrolaria	FooDB	31437929
Plant	Garcinia mangostana	FooDB	31437929
Plant	Corchorus olitorius	FooDB	31437929
Plant	Juglans nigra	FooDB	31437929
Plant	Dioscorea pentaphylla	FooDB	31437929
Plant	Cinnamomum verum	FooDB	31437929
Plant	Glycine max	FooDB	31437929
Plant	Lathyrus sativus	FooDB	31437929
Plant	Allium tuberosum	FooDB	31437929
Plant	Petasites japonicus	FooDB	31437929
Plant	Gaylussacia baccata	FooDB	31437929
Plant	Prunus tomentosa	FooDB	31437929
Plant	Mentha x piperita	FooDB	31437929
Plant	Ocimum basilicum	FooDB	31437929
Plant	Maranta arundinacea	FooDB	31437929
Plant	Matteuccia struthiopteris	FooDB	31437929
Plant	Cucurbita moschata	FooDB	31437929
Plant	Citrus limon	FooDB	31437929
Plant	Macadamia	FooDB	31437929
Plant	Tilia	FooDB	31437929
Plant	Apium graveolens var. rapaceum	FooDB	31437929
Plant	Papaver	FooDB	31437929
Plant	Vaccinium myrtilloides	FooDB	31437929
Plant	Rosa	FooDB	31437929
Plant	Capsicum annuum var. annuum	FooDB	31437929
Plant	Sesamum orientale	FooDB	31437929
Plant	Nelumbo	FooDB	31437929
Plant	Brassica oleracea var. conica	FooDB	31437929
Plant	Annona cherimola	FooDB	31437929
Plant	Brassica rapa var. pekinensis	FooDB	31437929
Plant	Brassica rapa	FooDB	31437929
Plant	Lippia graveolens	FooDB	31437929
Plant	Prunus	FooDB	31437929
Plant	Citrus sinensis	FooDB	31437929
Plant	Capparis spinosa	FooDB	31437929
Plant	Lens culinaris	FooDB	31437929
Plant	Vaccinium deliciosum	FooDB	31437929
Plant	Phaseolus lunatus	FooDB	31437929
Plant	Artocarpus heterophyllus	FooDB	31437929
Plant	Prunus virginiana	FooDB	31437929
Plant	Linum usitatissimum	FooDB	31437929
Plant	Musa acuminata	FooDB	31437929
Plant	Citrullus lanatus	FooDB	31437929
Plant	Vigna unguiculata ssp. unguiculata	FooDB	31437929
Plant	Macadamia tetraphylla	FooDB	31437929
Plant	Prunus domestica	FooDB	31437929
Plant	Prunus armeniaca	FooDB	31437929
Plant	Phyllostachys edulis	FooDB	31437929
Plant	Lagenaria siceraria	FooDB	31437929
Plant	Carum carvi	FooDB	31437929
Plant	Allium schoenoprasum	FooDB	31437929
Plant	Citrus reticulata	FooDB	31437929
Plant	Carissa macrocarpa	FooDB	31437929
Plant	Averrhoa carambola	FooDB	31437929
Plant	Satureja hortensis	FooDB	31437929
Plant	Brassica rapa var. rapa	FooDB	31437929
Plant	Anethum graveolens	FooDB	31437929
Plant	Sorbus aucuparia	FooDB	31437929
Plant	Coriandrum sativum	FooDB	31437929
Plant	Nelumbo nucifera	FooDB	31437929
Plant	Bertholletia excelsa	FooDB	31437929
Plant	Cymbopogon citratus	FooDB	31437929
Plant	Brassica oleracea var. costata	FooDB	31437929
Plant	Panax	FooDB	31437929
Plant	Ceratonia siliqua	FooDB	31437929
Plant	Luffa aegyptiaca	FooDB	31437929
Plant	Anacardium occidentale	FooDB	31437929
Plant	Carthamus tinctorius	FooDB	31437929
Plant	Cicer arietinum	FooDB	31437929
Plant	Rubus occidentalis	FooDB	31437929
Plant	Vigna umbellata	FooDB	31437929
Plant	Camellia sinensis	FooDB	31437929
Plant	Allium fistulosum	FooDB	31437929
Plant	Capsicum	FooDB	31437929
Plant	Vaccinium alaskaense	FooDB	31437929
Plant	Lupinus	FooDB	31437929
Plant	Tilia cordata	FooDB	31437929
Plant	Prunus persica var. nucipersica	FooDB	31437929
Plant	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant	Eriobotrya japonica	FooDB	31437929
Plant	Durio zibethinus	FooDB	31437929
Plant	Brassica napus var. pabularia	FooDB	31437929
Plant	Phaseolus vulgaris	FooDB	31437929
Plant	Oenothera biennis	FooDB	31437929
Plant	Diospyros kaki	FooDB	31437929
Plant	Ribes glandulosum	FooDB	31437929
Plant	Theobroma cacao	FooDB	31437929
Plant	Daucus carota ssp. sativus	FooDB	31437929
Plant	Virola surinamensis	FooDB	31437929
Plant	Verbena officinalis	FooDB	31437929
Plant	Rumex acetosa	FooDB	31437929
Plant	Vaccinium oxycoccos	FooDB	31437929
Plant	Vaccinium myrtillus	FooDB	31437929
Plant	Brassica oleracea var. capitata	FooDB	31437929
Plant	Syzygium aromaticum	FooDB	31437929
Plant	Pyrus pyrifolia	FooDB	31437929
Plant	Vicia faba	FooDB	31437929
Plant	Vaccinium parvifolium	FooDB	31437929
Plant	Aloysia triphylla	FooDB	31437929
Plant	Capsicum chinense	FooDB	31437929
Plant	Theobroma grandiflorum	FooDB	31437929
Plant	Vaccinium reticulatum	FooDB	31437929
Plant	Solanum quitoense	FooDB	31437929
Plant	Ginkgo biloba	FooDB	31437929
Plant	Vigna unguiculata ssp. cylindrica	FooDB	31437929
Plant	Flammulina velutipes	FooDB	31437929
Plant	Satureja montana	FooDB	31437929
Plant	Citrus japonica	FooDB	31437929
Plant		FooDB	31437929
Plant	Vitis vinifera	FooDB	31437929
Plant	Prunus avium	FooDB	31437929
Plant	Perideridia oregana	FooDB	31437929
Plant	Capsicum annuum	FooDB	31437929
Plant	Vaccinium arboreum	FooDB	31437929
Plant	Pouteria sapota	FooDB	31437929
Plant	Wasabia japonica	FooDB	31437929
Plant	Piper nigrum	FooDB	31437929
Plant	Origanum onites	FooDB	31437929
Plant	Origanum vulgare	FooDB	31437929
Plant	Viburnum edule	FooDB	31437929
Plant	Dioscorea	FooDB	31437929
Plant	Brassica oleracea var. italica	FooDB	31437929
Plant	Momordica charantia	FooDB	31437929
Plant	Vaccinium uliginosum	FooDB	31437929
Plant	Castanea	FooDB	31437929
Plant	Rubus ursinus x idaeus	FooDB	31437929
Plant	Solanum melongena	FooDB	31437929
Plant	Cirsium	FooDB	31437929
Plant	Pleurotus ostreatus	FooDB	31437929
Plant	Opuntia	FooDB	31437929
Plant	Anthriscus cerefolium	FooDB	31437929
Plant	Raphanus sativus var. sativus	FooDB	31437929
Plant	Colocasia esculenta	FooDB	31437929
Plant	Prunus persica var. persica	FooDB	31437929
Plant	Myristica fragrans	FooDB	31437929
Plant	Nuphar lutea	FooDB	31437929
Plant	Lupinus albus	FooDB	31437929
Plant	Pachyrhizus erosus	FooDB	31437929
Plant	Cichorium endivia	FooDB	31437929
Plant	Apium graveolens	FooDB	31437929
Plant	Elaeis	FooDB	31437929
Plant	Cinnamomum	FooDB	31437929
Plant	Ribes uva-crispa	FooDB	31437929
Plant	Feijoa sellowiana	FooDB	31437929
Plant	Dysphania ambrosioides	FooDB	31437929
Plant	Raphanus sativus var. niger	FooDB	31437929
Plant	Photinia melanocarpa	FooDB	31437929
Plant	Salvia officinalis	FooDB	31437929
Plant	Rheum rhabarbarum	FooDB	31437929
Plant	Vaccinium	FooDB	31437929
Plant	Lablab purpureus	FooDB	31437929
Plant	Crocus sativus	FooDB	31437929
Plant	Cydonia oblonga	FooDB	31437929
Plant	Citrus maxima	FooDB	31437929
Plant	Syzygium jambos	FooDB	31437929
Plant	Annona muricata	FooDB	31437929
Plant	Salix pulchra	FooDB	31437929
Plant	Castanea sativa	FooDB	31437929
Plant	Cucurbita	FooDB	31437929
Plant	Fagus	FooDB	31437929
Plant	Opuntia cochenillifera	FooDB	31437929
Plant	Vaccinium ovatum	FooDB	31437929
Plant	Cocos nucifera	FooDB	31437929
Plant	Tamarindus indica	FooDB	31437929
Plant	Phaseolus coccineus	FooDB	31437929
Plant	Thymus pulegioides	FooDB	31437929
Plant	Mespilus germanica	FooDB	31437929
Plant	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Brassica rapa var. perviridis	FooDB	31437929
Plant	Mentha aquatica	FooDB	31437929
Plant	Salvia elegans	FooDB	31437929
Plant	Mentha	FooDB	31437929
Plant	Solanum tuberosum	FooDB	31437929
Plant	Psidium guajava	FooDB	31437929
Plant	Sagittaria latifolia	FooDB	31437929
Plant	Olea europaea	FooDB	31437929
Plant	Sambucus	FooDB	31437929
Plant	Pinus	FooDB	31437929
Plant	Syzygium cumini	FooDB	31437929
Plant	Tilia tomentosa	FooDB	31437929
Plant	Daucus carota	FooDB	31437929
Plant	Typha angustifolia	FooDB	31437929
Plant	Vaccinium vitis-idaea	FooDB	31437929
Plant	Empetrum nigrum	FooDB	31437929
Plant	Valerianella locusta	FooDB	31437929
Plant	Myrica rubra	FooDB	31437929
Plant	Vaccinium angustifolium x vaccinium corymbosum	FooDB	31437929
Plant	Sisymbrium	FooDB	31437929
Plant	Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant	Vanilla	FooDB	31437929
Plant	Raphanus sativus	FooDB	31437929
Plant	Vigna radiata	FooDB	31437929
Plant	Carya	FooDB	31437929
Plant	Prunus dulcis	FooDB	31437929
Plant	Manihot esculenta	FooDB	31437929
Plant	Physalis philadelphica var. immaculata	FooDB	31437929
Plant	Borago officinalis	FooDB	31437929
Plant	Hyssopus officinalis	FooDB	31437929
Plant	Beta vulgaris ssp. cicla	FooDB	31437929
Plant	Scorzonera hispanica	FooDB	31437929
Plant	Vigna unguiculata ssp. sesquipedalis	FooDB	31437929
Plant	Angelica keiskei	FooDB	31437929
Plant	Ipomoea aquatica	FooDB	31437929
Plant	Musa x paradisiaca	FooDB	31437929
Plant	Cuminum cyminum	FooDB	31437929
Plant	Rubus spectabilis	FooDB	31437929
Plant	Allium sativum	FooDB	31437929
Plant	Arachis hypogaea	FooDB	31437929
Plant	Rubus idaeus	FooDB	31437929
Plant	Cantharellus cibarius	FooDB	31437929
Plant	Fragaria x ananassa	FooDB	31437929
Plant	Pyrus communis	FooDB	31437929
Plant	Sinapis alba	FooDB	31437929
Plant	Apium graveolens var. secalinum	FooDB	31437929
Plant	Brassica ruvo	FooDB	31437929
Plant	Morus nigra	FooDB	31437929
Plant	Solanum lycopersicum	FooDB	31437929
Plant	Abelmoschus esculentus	FooDB	31437929
Plant	Moringa oleifera	FooDB	31437929
Plant	Pinus edulis	FooDB	31437929
Plant	Passiflora edulis	FooDB	31437929
Plant	Vigna angularis	FooDB	31437929
Plant	Opuntia macrorhiza	FooDB	31437929
Plant	Mentha spicata	FooDB	31437929
Plant	Helianthus annuus	FooDB	31437929
Plant	Cucurbita pepo var. clypeata	FooDB	31437929
Plant	Manilkara zapota	FooDB	31437929
Plant	Corylus	FooDB	31437929
Plant	Malus	FooDB	31437929
Plant	Pisum sativum	FooDB	31437929
Plant	Juglans	FooDB	31437929
Plant	Zingiber officinale	FooDB	31437929
Plant	Petroselinum crispum	FooDB	31437929
Plant	Sambucus nigra	FooDB	31437929
Plant	Allium cepa	FooDB	31437929
Plant	Ribes nigrum	FooDB	31437929
Plant	Mangifera indica	FooDB	31437929
Plant	Illicium verum	FooDB	31437929
Plant	Chamaemelum nobile	FooDB	31437929
Plant	Laurus nobilis	FooDB	31437929
Plant		FooDB	31437929
Plant	Auricularia auricula-judae	FooDB	31437929
Plant	Attalea speciosa	FooDB	31437929
Plant	Juglans ailanthifolia	FooDB	31437929
Plant	Melissa officinalis	FooDB	31437929
Plant	Hippophae rhamnoides	FooDB	31437929
Plant	Spinacia oleracea	FooDB	31437929
Plant	Polygonum alpinum	FooDB	31437929
Plant	Brassica juncea	FooDB	31437929
Plant	Pediomelum esculentum	FooDB	31437929
Plant	Auricularia polytricha	FooDB	31437929
Plant	Camellia oleifera	FooDB	31437929
Plant	Carica papaya	FooDB	31437929
Plant	Vaccinium corymbosum	FooDB	31437929
Plant	Actinidia chinensis	FooDB	31437929
Plant	Chrysanthemum coronarium	FooDB	31437929
Plant	Eleocharis dulcis	FooDB	31437929
Plant	Thymus vulgaris	FooDB	31437929
Plant	Medicago sativa	FooDB	31437929
Plant	Vigna mungo	FooDB	31437929
Plant	Pimenta dioica	FooDB	31437929
Plant	Rubus arcticus	FooDB	31437929
Plant	Agaricus bisporus	FooDB	31437929
Plant	Cajanus cajan	FooDB	31437929
Plant	Origanum majorana	FooDB	31437929
Plant	Rumex articus	FooDB	31437929
Plant	Armoracia rusticana	FooDB	31437929
Plant	Prunus persica	FooDB	31437929
Plant	Hibiscus sabdariffa	FooDB	31437929
Plant	Benincasa hispida	FooDB	31437929
Plant	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Canarium ovatum	FooDB	31437929
Plant	Ribes aureum var. villosum	FooDB	31437929
Plant		FooDB	31437929
Plant	Brassica oleracea var. gemmifera	FooDB	31437929
Plant	Foeniculum vulgare	FooDB	31437929
Plant	Brassica oleracea var. gongylodes	FooDB	31437929
Plant	Phoenix dactylifera	FooDB	31437929
Plant	Vaccinium macrocarpon	FooDB	31437929
Plant	Arctium lappa	FooDB	31437929
Plant	Juglans cinerea	FooDB	31437929
Plant	Prunus cerasus	FooDB	31437929
Plant	Artocarpus altilis	FooDB	31437929
Plant	Eruca vesicaria ssp. sativa	FooDB	31437929
Plant	Citrus x paradisi	FooDB	31437929
Plant	Rosmarinus officinalis	FooDB	31437929
Plant	Cynara scolymus	FooDB	31437929
Plant	Vigna unguiculata	FooDB	31437929
Plant	Ficus carica	FooDB	31437929
Plant	Lentinus edodes	FooDB	31437929
Plant	Cyathea	FooDB	31437929
Plant	Metroxylon sagu	FooDB	31437929
Plant	Vitis rotundifolia	FooDB	31437929
Plant	Brosimum alicastrum	FooDB	31437929
Plant	Psidium cattleianum	FooDB	31437929
Plant	Beta vulgaris var. rubra	FooDB	31437929
Plant	Lepidium sativum	FooDB	31437929
Plant	Castanea mollissima	FooDB	31437929
Plant	Helianthus tuberosus	FooDB	31437929
Plant	Morus	FooDB	31437929
Plant	Phytolacca americana	FooDB	31437929
Plant	Grifola frondosa	FooDB	31437929
Plant	Vitis labrusca	FooDB	31437929
Plant		FooDB	31437929
Plant	Artemisia vulgaris	FooDB	31437929
Plant	Tetragonia tetragonioides	FooDB	31437929
Plant	Cucumis metuliferus	FooDB	31437929
Plant	Nephelium lappaceum	FooDB	31437929
Plant	Myrica	FooDB	31437929
Plant	Corylus avellana	FooDB	31437929

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:0x00007fa5085174d0>

3D MOL for #<Metabolite:0x00007fa5085174d0>

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3D-SDF for #<Metabolite:0x00007fa5085174d0>

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3D PDB for #<Metabolite:0x00007fa5085174d0>

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Structure for #<Metabolite:0x00007fa5085174d0>

3D Structure for #<Metabolite:0x00007fa5085174d0>