Showing Compound Citicoline (FDB022608)

Record Information

Version

1.0

Creation date

2011-09-21 00:16:49 UTC

Update date

2020-09-17 15:41:05 UTC

Primary ID

FDB022608

Secondary Accession Numbers

FDB030718

Chemical Information

FooDB Name

Citicoline

Description

Citicoline, also known as CDP-colina or nicholin, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. 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 drug. Citicoline is an extremely weak basic (essentially neutral) compound (based on its pKa). Citicoline is an essential intermediate in the biosynthetic pathway of structural phospholipids in cell membranes, particularly phosphatidylcholine. Citicoline exists in all eukaryotes, ranging from yeast to humans. In humans, citicoline is involved in phospholipid biosynthesis. Outside of the human body, Citicoline has been detected, but not quantified in, several different foods, such as mountain yams, oil-seed camellia, rowals, mango, and pineappple sages. This could make citicoline a potential biomarker for the consumption of these foods. 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. Thus, citicoline has been experimentally shown to increase norepinephrine and dopamine levels in the CNS. Citicoline activates biosynthesis of structural phospholipids of neuronal membranes, increases brain metabolism, and acts upon the levels of different neurotransmitters. 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. 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. 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.

CAS Number

987-78-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
5'-Diphosphocholine, cytidine	HMDB
[2-CYTIDYLATE-o'-onyloxyl]-ethyl-trimethyl-ammonium	ChEBI
[2-CYTIDYLATE-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium	ChEBI
[2-CYTIDYLic acid-o'-onyloxyl]-ethyl-trimethyl-ammonium	Generator
[2-CYTIDYLic acid-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium	Generator
Audes	HMDB
CDP Choline	HMDB
CDP-Choline	HMDB
CDP-choline	hmdb
CDP-Colina	ChEBI

Showing 1 to 10 of 85 entries

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

Chemical Formula

C14H26N4O11P2

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

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

Isomeric 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

Average Molecular Weight

488.324

Monoisotopic Molecular Weight

488.107330718

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Subcellular:

Cytoplasm

Organ and components:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Citicoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-7649200000-859d046834f1fbd3d535	Spectrum
Predicted GC-MS	Citicoline, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00yi-7947012000-9f83d07fb5a59a93e770	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0001900000-a9f38ff6b185b45f04b3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03e9-0590000000-b021677d064d65810ee0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-0900000000-7570bbb10dd9fa288442	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-0000900000-8b411373962b073b4d22	2012-08-31	View Spectrum
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
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-01qi-1932200000-9c3803cefdd9c6285a7c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-6505900000-3d534aab6e40915c3642	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-6505900000-fc13e5ad403e7faf8218	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-6505900000-3d534aab6e40915c3642	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-6505900000-fc13e5ad403e7faf8218	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0000900000-8b411373962b073b4d22	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0001900000-6e7cc437ad79eb13c032	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01qi-1932200000-4a7ae92c6e127d2ce453	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-2900100000-0ce672506aae2d1e5eef	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3900000000-c05f3e5b6782e32eeebb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-8900000000-17466c845e643c77969b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01p9-0501900000-be567596c9f980cea8c2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-3904100000-4c2e6535887540a12444	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fu-9600000000-e42f82159eabb4ec781a	2017-09-01	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16436

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01413

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

1485298

KNApSAcK ID

Not Available

HET ID

CDC

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Citicoline

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Choline-phosphate cytidylyltransferase A	PCYT1A	P49585
Choline-phosphate cytidylyltransferase B	PCYT1B	Q9Y5K3
Phosphatidylcholine:ceramide cholinephosphotransferase 1	SGMS1	Q86VZ5
Phosphatidylcholine:ceramide cholinephosphotransferase 2	SGMS2	Q8NHU3