CHEBI:16436 - CDP-choline

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ChEBI Name CDP-choline
ChEBI ID CHEBI:16436
Definition A member of the class of phosphocholines that is the choline ester of CDP. It is an intermediate obtained in the biosynthetic pathway of structural phospholipids in cell membranes.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41440, CHEBI:13268, CHEBI:3268, CHEBI:20867
Supplier Information ChemicalBook:CB42130435, ChemicalBook:CB6139144, eMolecules:1934538, ZINC000008036012
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Phytomenadione, also known as vitamin K1, phylloquinone, or phytonadione, is a vitamin found in food and used as a dietary supplement. It is on the World Health Organization's List of Essential Medicines. It is used to treat certain bleeding disorders, including warfarin overdose, vitamin K deficiency, and obstructive jaundice. Use is typically recommended by mouth, intramuscular injection or injection under the skin. When given by injection benefits are seen within two hours. It is also recommended for preventing and treating vitamin K deficiency bleeding in infants. Many countries in the world choose intramuscular injections in newborn to keep them safe from vitamin K deficiency bleeding. It is considered a safe treatment and saves many children from death and severe neurologic deficit every year. Side effects when given by injection may include pain at the site of injection. Severe allergic reactions may occur when it is injected into a vein or muscle, but this has mainly happened when large doses of a certain type of supplement containing castor oil were given intravenously. Use during pregnancy is considered safe, use is also likely okay during breastfeeding. It works by supplying a required component for making a number of blood clotting factors. Food sources include green vegetables, vegetable oil, and some fruit. Phytomenadione was first isolated in 1939. In 1943 Edward Doisy and Henrik Dam were given a Nobel Prize for its discovery.
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Formula C14H26N4O11P2
Net Charge 0
Average Mass 488.32412
Monoisotopic Mass 488.10733
InChI 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
InChIKey RZZPDXZPRHQOCG-OJAKKHQRSA-N
SMILES C[N+](C)(C)CCOP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1ccc(N)nc1=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Application(s): psychotropic drug
A loosely defined grouping of drugs that have effects on psychological function.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
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ChEBI Ontology
Outgoing CDP-choline (CHEBI:16436) has functional parent CDP (CHEBI:17239)
CDP-choline (CHEBI:16436) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
CDP-choline (CHEBI:16436) has role human metabolite (CHEBI:77746)
CDP-choline (CHEBI:16436) has role mouse metabolite (CHEBI:75771)
CDP-choline (CHEBI:16436) has role neuroprotective agent (CHEBI:63726)
CDP-choline (CHEBI:16436) has role psychotropic drug (CHEBI:35471)
CDP-choline (CHEBI:16436) is a nucleotide-(amino alcohol)s (CHEBI:25604)
CDP-choline (CHEBI:16436) is a phosphocholines (CHEBI:36700)
CDP-choline (CHEBI:16436) is conjugate base of CDP-choline(1+) (CHEBI:49086)
Incoming CDP-choline(1+) (CHEBI:49086) is conjugate acid of CDP-choline (CHEBI:16436)
IUPAC Name
5'-O-[hydroxy({[2-(trimethylammonio)ethoxy]phosphinato}oxy)phosphoryl]cytidine
INNs Sources
citicolina ChemIDplus
citicolinum ChemIDplus
Synonyms Sources
[2-CYTIDYLATE-O'-PHOSPHONYLOXYL]-ETHYL-TRIMETHYL-AMMONIUM PDBeChem
CDP-colina ChemIDplus
Citicoline KEGG COMPOUND
citidin difosfato de colina ChemIDplus
cyticholine ChEBI
Cytidindiphosphocholin ChemIDplus
cytidine 5'-(choline diphosphate) ChemIDplus
cytidine 5'-(cholinyl pyrophosphate) ChemIDplus
Cytidine 5'-diphosphocholine KEGG COMPOUND
cytidine 5'-diphosphoric choline ChemIDplus
Manual Xrefs Databases
664 DrugCentral
C00007231 KNApSAcK
C00307 KEGG COMPOUND
CDC PDBeChem
Citicoline Wikipedia
D00057 KEGG DRUG
DB04290 DrugBank
HMDB0001413 HMDB
View more database links
Registry Numbers Types Sources
4170138 Reaxys Registry Number Reaxys
987-78-0 CAS Registry Number ChemIDplus
Citations Types Sources
10701532 PubMed citation Europe PMC
10796523 PubMed citation Europe PMC
36524681 PubMed citation Europe PMC
37196134 PubMed citation Europe PMC
37449595 PubMed citation Europe PMC
38478324 PubMed citation Europe PMC
38479101 PubMed citation Europe PMC
38484849 PubMed citation Europe PMC
38760804 PubMed citation Europe PMC
38776883 PubMed citation Europe PMC
8709678 PubMed citation Europe PMC
Last Modified
22 October 2024