MiMeDB: Showing metabocard for Citicoline (MMDBc0032916)

Not Available

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

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000467	Phosphorylcholine	Citicoline	phosphate cytidylyltransferase 1, choline, alpha		VMH; KEGG	30371894
MMDBr0009372	Citicoline	Cytidine monophosphate	Not Available		VMH	30371894

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

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	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:0x00007fdb71693a08>

3D MOL for #<Metabolite:0x00007fdb71693a08>

3D SDF for #<Metabolite:0x00007fdb71693a08>

3D-SDF for #<Metabolite:0x00007fdb71693a08>

PDB for #<Metabolite:0x00007fdb71693a08>

3D PDB for #<Metabolite:0x00007fdb71693a08>

SMILES for #<Metabolite:0x00007fdb71693a08>

INCHI for #<Metabolite:0x00007fdb71693a08>

Structure for #<Metabolite:0x00007fdb71693a08>

3D Structure for #<Metabolite:0x00007fdb71693a08>