Citicoline

Details

• Internal ID: b074200e-d2bc-435e-8a82-c43c31969102
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine ribonucleotides > Pyrimidine ribonucleoside diphosphates
• IUPAC Name: [[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] 2-(trimethylazaniumyl)ethyl phosphate
• SMILES (Canonical): C[N+](C)(C)CCOP(=O)([O-])OP(=O)(O)OCC1C(C(C(O1)N2C=CC(=NC2=O)N)O)O
• SMILES (Isomeric): C[N+](C)(C)CCOP(=O)([O-])OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)N)O)O
• 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
• InChI Key: RZZPDXZPRHQOCG-OJAKKHQRSA-N
• Popularity: 1,644 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₆N₄O₁₁P₂
• Molecular Weight: 488.32 g/mol
• Exact Mass: 488.10733165 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -4.00
• Atomic LogP (AlogP): -2.23
• H-Bond Acceptor: 13
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

• cytidine 5'-diphosphocholine
• CDP-choline
• 987-78-0
• citicholine
• cytidine diphosphate choline
• Citidoline
• Cytidoline
• Difosfocin
• Cyscholin
• Citicolinum
• Citicolina
• CDP-colina
• cyticholine
• Cytidine 5'-diphosphoric choline
• Haocolin
• Nicholin
• Niticolin
• Recofnan
• Recognan
• Somazina
• Suncholin
• Colite
• Ensign
• Cytidindiphosphocholin
• Cytidine 5'-(choline diphosphate)
• Cytidine 5'-(cholinyl pyrophosphate)
• Cytidine diphosphocholine
• Cytidine diphosphorylcholine
• Choline cytidine diphosphate
• Cytidine choline diphosphate
• citidin difosfato de colina
• Emicholin
• Meibis
• Choline 5'-cytidine diphosphate
• CDP-cholin
• Cereb
• Cytidine 5'-diphosphate choline
• Cytidine diphosphate choline ester
• Cytidinediphosphoric choline
• [2-CYTIDYLATE-O'-PHOSPHONYLOXYL]-ETHYL-TRIMETHYL-AMMONIUM
• Cytidine 5'-(trihydrogen diphosphate), P'-(2-(trimethylammonio)ethyl) ester, inner salt
• IP 302
• IP-302
• Choline cytidine 5'-pyrophosphate ester
• Choline, ester with cytidine 5'-pyrophosphate
• CDP-cholin [German]
• CDP-colina [Spanish]
• Startonyl
• Ubelin
• Citicoline [INN:JAN]
• Citicolinum [INN-Latin]
• Citicolina [INN-Spanish]
• 536BQ2JVC7
• CHEBI:16436
• {2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]ethyl}trimethylazanium
• 2-(((((((2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)oxidophosphoryl)oxy)-N,N,N-trimethylethanaminium
• Cytidindiphosphocholin [German]
• Cytidine diphosphate cholin ester
• EINECS 213-580-7
• Citidin difosfato de colina [Spanish]
• Cytidine 5-diphosphocholine
• NSC 122002
• BRN 4170138
• UNII-536BQ2JVC7
• Cytidine, 5'-pyrophosphate, ester with choline
• Cytidine 5'-(trihydrogen diphosphate), P'-[2-(trimethylammonio)ethyl] ester, inner salt
• Nicholin (TN)
• Citicoline (JP17/INN)
• cytidine diphosphate-choline
• CDP-choline (neutral charge)
• SCHEMBL221081
• DTXSID9048431
• RZZPDXZPRHQOCG-OJAKKHQRSA-N
• MFCD00868097
• AKOS025312525
• CCG-269597
• DB04290
• DB12153
• Choline, hydroxide, 5'-ester with cytidine 5'-(trihydrogen pyrophosphate), inner salt
• Cytidine 5'-(trihydrogen diphosphate), mono(2-(trimethylammonio)ethyl) ester, hydroxide, inner salt
• C3438
• C00307
• D00057
• D81851
• EN300-7398882
• A847982
• W-100063
• Q28529682
• Cytidine diphosphate-choline;CDP-Choline;Cytidine 5'-diphosphocholine
• 5'-O-[(S)-hydroxy({[2-(trimethylammonio)ethoxy]phosphinato}oxy)phosphoryl]cytidine
• 5'-O-[hydroxy({[2-(trimethylammonio)ethoxy]phosphinato}oxy)phosphoryl]cytidine
• Cytidine 5'-(trihydrogen diphosphate), P'-[2-(trimethylammonio)ethyl]ester, inner salt

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6941	69.41%
Caco-2	-	0.8800	88.00%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.3902	39.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9356	93.56%
OATP1B3 inhibitior	+	0.9346	93.46%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9269	92.69%
P-glycoprotein inhibitior	-	0.5853	58.53%
P-glycoprotein substrate	-	0.7365	73.65%
CYP3A4 substrate	+	0.6109	61.09%
CYP2C9 substrate	-	0.7978	79.78%
CYP2D6 substrate	-	0.8547	85.47%
CYP3A4 inhibition	-	0.8877	88.77%
CYP2C9 inhibition	-	0.8439	84.39%
CYP2C19 inhibition	-	0.8009	80.09%
CYP2D6 inhibition	-	0.8274	82.74%
CYP1A2 inhibition	-	0.8289	82.89%
CYP2C8 inhibition	-	0.6829	68.29%
CYP inhibitory promiscuity	-	0.9675	96.75%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.5401	54.01%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.9613	96.13%
Skin irritation	-	0.7668	76.68%
Skin corrosion	-	0.9196	91.96%
Ames mutagenesis	-	0.8628	86.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.6553	65.53%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.9500	95.00%
skin sensitisation	-	0.8352	83.52%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.5593	55.93%
Acute Oral Toxicity (c)	IV	0.4967	49.67%
Estrogen receptor binding	+	0.6513	65.13%
Androgen receptor binding	+	0.8750	87.50%
Thyroid receptor binding	+	0.5653	56.53%
Glucocorticoid receptor binding	-	0.8662	86.62%
Aromatase binding	+	0.6276	62.76%
PPAR gamma	+	0.6398	63.98%
Honey bee toxicity	-	0.8196	81.96%
Biodegradation	+	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.4451	44.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.53%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	98.40%	95.93%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	96.05%	80.33%
CHEMBL2581	P07339	Cathepsin D	89.75%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.74%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.49%	94.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	87.32%	93.10%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	86.25%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.22%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.75%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.99%	99.23%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.07%	96.90%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 13804
• LOTUS: LTS0000263
• wikiData: Q28529682