Basic information
- CAS
987-78-0- Standard SMILES
C[N+](C)(C)CCOP(=O)([O-])OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1O- InChIKey
RZZPDXZPRHQOCG-OJAKKHQRSA-N- Molecular formula
- C14H26N4O11P2
- Average molar mass
- 488.32 g/mol
- Monoisotopic mass
- 488.10733165
Overview
CDP-choline is 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. It has a role as a psychotropic drug, a neuroprotective agent, a mouse metabolite, a Saccharomyces cerevisiae metabolite and a human metabolite. It is a member of nucleotide-(amino alcohol)s and a member of phosphocholines. It is functionally related to a CDP. It is a conjugate base of a CDP-choline(1+).
Names & identifiers
- Preferred name
- Citicoline
- IUPAC
- [[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] 2-(trimethylazaniumyl)ethyl phosphate
- English name
- Cytidine 5'-Diphosphocholine
- Molecular formula
- C14H26N4O11P2
- Molecular weight
- 488.33
Names & synonyms
citicolinecytidine 5'-diphosphocholine987-78-0CDP-cholineciticholineCiticolinaCiticolinumcytidine diphosphate cholineNicholinCDP-colinaCytidindiphosphocholinCytidine 5'-diphosphoric choline
Show more names
ReaginsomazinaCiticoline CDP cholineAudescerebRexort
Cytidine 5'-(choline diphosphate)Cytidine 5'-(cholinyl pyrophosphate)cidifoscitidin difosfato de colinaCDP-cholinCytidine 5-diphosphocholineCytidine 5'-diphosphate cholineCDP choline
Database identifiers
- CAS
987-78-0- PubChem CID
- 13804
- DTXSID
DTXSID9048431- ChEMBL
CHEMBL1231700- ChEBI
CHEBI:16436- EC Number
- 213-580-7
- Nikkaji
- J55.713G
Properties
Computed structural properties
- XLogP
- -4
- Topological polar surface area
- 214 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 10
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 821
Experimental & physicochemical properties
Collision Cross Section
197.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
208.98 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
210.2 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
Physicochemical properties
- Melting point
- 185 °C · >185°C (dec.)
- alpha
- 25 · D25 +19.0° (c = 0.86 in H2O)
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- solubility
- Water (Sparingly)
- pka
- 4.4 · 4.4(at 25℃)
- form
- Solid
- color
- White
- Stability
- Moisture Sensitive
- InChIKey
- RZZPDXZPRHQOCG-APGYLPRWNA-N
- SMILES
- O[C@@H]1[C@@H]([C@@H](COP(O)(=O)OP([O-])(=O)OCC[N+](C)(C)C)O[C@H]1N1C=CC(N)=NC1=O)O |&1:1,2,3,21,r|
- LogP
- -7.07 · -7.070 (est)
- CAS DataBase Reference
- 987 · 987-78-0(CAS DataBase Reference)
- FDA UNII
- 536 BQ2JVC7 · 536BQ2JVC7
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 335 · H335-H315-H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
- Toxicity
- 50 in · LD50 in mice, rats (mg/kg): 4600 ±335, 4150 ±370 i.v.; both species 8 g/kg orally (Grau)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationRegulation (EC) No 258/1997
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
citicoline
DILI Negative
DOI:10.1016/j.drudis.2019.09.022
Safety data
- Toxicity
- LD50 in mice, rats (mg/kg): 4600 ±335, 4150 ±370 i.v.; both species 8 g/kg orally (Grau)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H335-H315-H319
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
MeSH Pharmacological ClassificationDrugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms.
Applications
DescriptionCiticoline whose chemical name choline cytosine nucleoside-5'-diphosphate monosodium salt, is a precursor for lecithin biosynthesis, and when brain function declines, the content of lecithin in brain tissue is significantly reduced.
UsesCytidine 5'-Diphosphocholine is used as antidepressant, 5HT uptake inhibitor.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
山东天微医药科技有限公司+86-18653895227 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
Syntechem Co.,Ltd[email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海钰康生物科技有限公司+86-18930848214 +86-021-56762820 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
杭州东帆化学有限公司86-0571-85151182
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
新乡市翌诚生物科技有限公司0373-5799336 18937330588 · [email protected]
Beckmann-Kenko GmbH+49 4241 9308 88 · [email protected]
Wuhan Demeikai Biotechnology Co., Ltd+8618942921723 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
南京诺利斯医药科技有限公司13901585132 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
苏州麦轮生物科技有限公司13771927830 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
Xunteng International Trading Co.,Limited—
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
湖南华腾制药有限公司400-8592883 15367835770 · [email protected]
上海创赛科技有限公司400-6087598 15021221957 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
上海乾劲化工科技有限公司021-20900665 17321230821 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
上海兴鲁化工科技有限公司02120970332 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
西安康诺化工有限公司029-86107037 15829389671 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
杭州六可生物科技有限公司+86-571-86912261 19975279805 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
芜湖诺威化学技术有限公司0553-8233716 18055326116 · [email protected]
杭州鼎燕化工有限公司0571-87157530-8003 18049756717 · [email protected]
南京派琪生物科技有限公司13342904611 13342904611 · [email protected]
Additional notes
DefinitionChEBI: CDP-choline is a member of the class of phosphocholines that is the chloine ester of CDP. It is an intermediate obtained in the biosynthetic pathway of structural phospholipids in cell membranes. It has a role as a human metabolite, a psychotropic drug, a neuroprotective agent, a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is a member of phosphocholines and a member of nucleotide-(amino alcohol)s. It is functionally related to a CDP. It is a conjugate base of a CDP-choline(1+).
Related reactions
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Compound notes
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