Citicoline (BioDeep_00000859284)
Secondary id: BioDeep_00000000744
human metabolite Endogenous Chemicals and Drugs
代谢物信息卡片
{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[2-(trimethylazaniumyl)ethoxy]phosphoryl}oxy)phosphinic acid
化学式: C14H27N4O11P2+ (489.11515119999996)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 0.09%
分子结构信息
SMILES: C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OCC1C(C(C(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
描述信息
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) [HMDB]. Citicoline is found in many foods, some of which are chives, black walnut, kohlrabi, and abiyuch.
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).
N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics
D002491 - Central Nervous System Agents > D018697 - Nootropic Agents
同义名列表
31 个代谢物同义名
{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[2-(trimethylazaniumyl)ethoxy]phosphoryl}oxy)phosphinic acid; Cytidine 5-(trihydrogen diphosphoric acid), mono(2-(trimethylammonio)ethyl) ester; Cytidine 5-(trihydrogen diphosphate), mono(2-(trimethylammonio)ethyl) ester; Cytidine 5’-(cholinyl pyrophosphate); Cytidine 5-(cholinyl pyrophosphate); Cytidine diphosphate choline ester; Cytidine 5’-(choline diphosphate); Cytidine 5-(choline diphosphate); Cytidine 5’-diphosphate choline; Choline 5’-cytidine diphosphate; Choline 5-cytidine diphosphate; Cytidine 5-diphosphate choline; Choline, Cytidine Diphosphate; Diphosphate Choline, Cytidine; Choline cytidine diphosphate; cytidine diphosphate choline; Cytidine choline diphosphate; Cytidine diphosphorylcholine; 5-Diphosphocholine, Cytidine; Cytidine 5’-diphosphocholine; Cytidine 5 Diphosphocholine; cytidine 5-diphosphocholine; Cytidine diphosphocholine; cdp-choline(1+); Choline, CDP; citicholine; cyticholine; CDP-choline; CDP Choline; Citicoline; Cidifos
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:49086
- PubChem: 13805
- HMDB: HMDB0001413
- Wikipedia: Citicoline
- MeSH: Cytidine Diphosphate Choline
- MetaCyc: CDP-CHOLINE
- KNApSAcK: C00007231
- foodb: FDB022608
- chemspider: 13208
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
2 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(2)
- Acetylcholine synthesis:
Acetate ⟶ Acetyl-CoA - Glycerophospholipid biosynthetic pathway:
Glycerol ⟶ sn-glycerol-3-phosphate (glycerol-3-P)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Zhenhua Wang, Meng Yang, Yufan Yang, Yonglin He, Hongwu Qian. Structural basis for catalysis of human choline/ethanolamine phosphotransferase 1.
Nature communications.
2023 May; 14(1):2529. doi:
10.1038/s41467-023-38290-2. [PMID: 37137909] - Qin Zhang, Hong Zhang, Chun-Mei Yang, Bo Wang, Chen-Yang Li, Qi Li. [Mechanism of active ingredients in Periploca forrestii compound against rheumatoid arthritis based on integrative metabolomics and network pharmacology].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2023 Jan; 48(2):507-516. doi:
10.19540/j.cnki.cjcmm.20220913.702. [PMID: 36725240] - Cheng Zheng, Mingjin Qu, Yingmiao Liu, Junzhi Wang, Hanjie Ying. Design and optimizing a new CDP-choline in vitro multienzyme producing process starts from d-ribose.
Biotechnology and applied biochemistry.
2022 Jun; 69(3):1029-1035. doi:
10.1002/bab.2173. [PMID: 33885187] - Hussein M Eid, Adel A Ali, Ahmed M Abdelhaleem Ali, Essam M Eissa, Randa M Hassan, Fatma I Abo El-Ela, Amira H Hassan. Potential Use of Tailored Citicoline Chitosan-Coated Liposomes for Effective Wound Healing in Diabetic Rat Model.
International journal of nanomedicine.
2022; 17(?):555-575. doi:
10.2147/ijn.s342504. [PMID: 35153481] - Amin Osman Elzupir. Molecular Docking and Dynamics Investigations for Identifying Potential Inhibitors of the 3-Chymotrypsin-like Protease of SARS-CoV-2: Repurposing of Approved Pyrimidonic Pharmaceuticals for COVID-19 Treatment.
Molecules (Basel, Switzerland).
2021 Dec; 26(24):. doi:
10.3390/molecules26247458. [PMID: 34946540] - Meric Kocaturk, Zeki Yilmaz, Mehmet Cansev, Yesim Ozarda, Jose Joaquin Ceron, Ali Buturak, Ismail H Ulus. Choline or CDP-choline restores hypotension and improves myocardial and respiratory functions in dogs with experimentally - Induced endotoxic shock.
Research in veterinary science.
2021 Dec; 141(?):116-128. doi:
10.1016/j.rvsc.2021.10.010. [PMID: 34715589] - Hyeonseok Jeong, Sujung Yoon, Young-Hoon Sung, Jungyoon Kim, In Kyoon Lyoo, Deborah A Yurgelun-Todd, Perry F Renshaw. Effects of cytidine-5'-diphosphate choline on gray matter volumes in methamphetamine-dependent patients: A randomized, double-blind, placebo-controlled study.
Journal of psychiatric research.
2021 11; 143(?):215-221. doi:
10.1016/j.jpsychires.2021.09.006. [PMID: 34507102] - Cheng Zheng, Rongxin Miao, Yingmiao Liu, Yang Cao, Dong Liu, Junzhi Wang, Hanjie Ying. A Procedure to Design One-Pot Multi-enzyme System for Industrial CDP-Choline Production.
Applied biochemistry and biotechnology.
2021 Sep; 193(9):2769-2780. doi:
10.1007/s12010-021-03564-2. [PMID: 34117628] - Lucia E Rosas, Lauren M Doolittle, Lisa M Joseph, Hasan El-Musa, Michael V Novotny, Judy M Hickman-Davis, R Duncan Hite, Ian C Davis. Postexposure Liponucleotide Prophylaxis and Treatment Attenuates Acute Respiratory Distress Syndrome in Influenza-infected Mice.
American journal of respiratory cell and molecular biology.
2021 06; 64(6):677-686. doi:
10.1165/rcmb.2020-0465oc. [PMID: 33606602] - Abeer Salamah, Mostafa Mehrez, Amany Faheem, Doaa El Amrousy. Efficacy of Citicoline as a Neuroprotector in children with post cardiac arrest: a randomized controlled clinical trial.
European journal of pediatrics.
2021 Apr; 180(4):1249-1255. doi:
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Environmental science and pollution research international.
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Talanta.
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International journal of biological macromolecules.
2020 May; 150(?):380-388. doi:
10.1016/j.ijbiomac.2020.02.102. [PMID: 32057876] - Azadeh Aminzadeh, Ayda Salarinejad. Citicoline protects against lead-induced oxidative injury in neuronal PC12 cells.
Biochemistry and cell biology = Biochimie et biologie cellulaire.
2019 12; 97(6):715-721. doi:
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Medical hypotheses.
2019 Aug; 129(?):109245. doi:
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Nutrients.
2019 Jul; 11(7):. doi:
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Molecules (Basel, Switzerland).
2019 May; 24(9):. doi:
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Clinical rehabilitation.
2019 Apr; 33(4):642-652. doi:
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Journal of the College of Physicians and Surgeons--Pakistan : JCPSP.
2019 Apr; 29(4):324-327. doi:
10.29271/jcpsp.2019.04.324. [PMID: 30925953] - Su Myat Phyu, Chih-Chung Tseng, Tim Andrew Davies Smith. CDP-choline accumulation in breast and colorectal cancer cells treated with a GSK-3-targeting inhibitor.
Magma (New York, N.Y.).
2019 Apr; 32(2):227-235. doi:
10.1007/s10334-018-0719-3. [PMID: 30446846] - Cheng Zheng, Zhenjian Li, Haifeng Yang, Tianyi Zhang, Huanqing Niu, Dong Liu, Junzhi Wang, Hanjie Ying. Computation-aided rational design of a halophilic choline kinase for cytidine diphosphate choline production in high-salt condition.
Journal of biotechnology.
2019 Jan; 290(?):59-66. doi:
10.1016/j.jbiotec.2018.11.008. [PMID: 30445133] - Cecilia Zazueta, Mabel Buelna-Chontal, Arturo Macías-López, Nadia G Román-Anguiano, Héctor González-Pacheco, Natalia Pavón, Rashidi Springall, Alberto Aranda-Frausto, Rafael Bojalil, Alejandro Silva-Palacios, Rodrigo Velázquez-Espejel, Sonia Galvan Arzate, Francisco Correa. Cytidine-5'-Diphosphocholine Protects the Liver From Ischemia/Reperfusion Injury Preserving Mitochondrial Function and Reducing Oxidative Stress.
Liver transplantation : official publication of the American Association for the Study of Liver Diseases and the International Liver Transplantation Society.
2018 08; 24(8):1070-1083. doi:
10.1002/lt.25179. [PMID: 29679463] - M Castro-Gago, D Dacruz, C Gomez-Lado, J Eiris-Punal. [Treatment of choline kinase beta deficiency with citicoline].
Revista de neurologia.
2018 07; 67(1):40. doi:
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Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova.
2018 ; 118(1):18-22. doi:
10.17116/jnevro20181181118-22. [PMID: 29460900] - Yixiong Chen, Bing Li, Kai Cen, Yuzhen Lu, Siwei Zhang, Chengshu Wang. Diverse effect of phosphatidylcholine biosynthetic genes on phospholipid homeostasis, cell autophagy and fungal developments in Metarhizium robertsii.
Environmental microbiology.
2018 01; 20(1):293-304. doi:
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Journal of neuroendocrinology.
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Drug and chemical toxicology.
2018 Jan; 41(1):62-71. doi:
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Cell biology international.
2017 Dec; 41(12):1356-1366. doi:
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Toxicology and industrial health.
2017 Apr; 33(4):308-317. doi:
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2017 Feb; 101(4):1409-1417. doi:
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Shock (Augusta, Ga.).
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Irish journal of medical science.
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The FEBS journal.
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Biochimica et biophysica acta.
2013 Mar; 1831(3):523-32. doi:
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CNS & neurological disorders drug targets.
2013 Feb; 12(1):94-103. doi:
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Clinical interventions in aging.
2013; 8(?):131-7. doi:
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Journal of affective disorders.
2012 Dec; 143(1-3):257-60. doi:
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Journal of pharmaceutical and biomedical analysis.
2012 Dec; 71(?):144-7. doi:
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Neurological research.
2012 Sep; 34(7):649-56. doi:
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Vestnik oftalmologii.
2012 Jul; 128(4):27-31. doi:
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BMC genomics.
2012 Mar; 13(?):84. doi:
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Brain research bulletin.
2012 Feb; 87(2-3):286-94. doi:
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Neurochemistry international.
2012 Jan; 60(1):31-8. doi:
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Indian journal of pharmacology.
2012 Jan; 44(1):118-21. doi:
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International journal of molecular sciences.
2012; 13(3):3176-3188. doi:
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Evidence-based complementary and alternative medicine : eCAM.
2012; 2012(?):426215. doi:
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Biochemistry research international.
2012; 2012(?):738471. doi:
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PloS one.
2012; 7(5):e37293. doi:
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PloS one.
2012; 7(2):e31342. doi:
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Genome biology.
2011 Dec; 12(12):R123. doi:
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PLoS neglected tropical diseases.
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Biochimica et biophysica acta.
2011 Dec; 1811(12):1177-85. doi:
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Journal of inflammation (London, England).
2011 Jul; 8(?):17. doi:
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PLoS genetics.
2011 Jul; 7(7):e1002201. doi:
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Biochimica et biophysica acta.
2011 Jun; 1811(6):377-85. doi:
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Life sciences.
2011 Mar; 88(11-12):473-9. doi:
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Journal of addiction medicine.
2011 Mar; 5(1):57-64. doi:
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Journal of lipid research.
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American journal of physiology. Endocrinology and metabolism.
2011 Feb; 300(2):E402-9. doi:
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Neuroscience.
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Molecular systems biology.
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Omics : a journal of integrative biology.
2010 Oct; 14(5):563-74. doi:
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The Journal of biological chemistry.
2010 Jul; 285(30):22957-65. doi:
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Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis.
2010 Jun; 21(4):339-48. doi:
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Nutrition & metabolism.
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Breast cancer research and treatment.
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Biochimica et biophysica acta.
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The Journal of pharmacy and pharmacology.
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PLoS computational biology.
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Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2010 Apr; 35(5):1165-73. doi:
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Lipids in health and disease.
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BMC genomics.
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BMC neuroscience.
2010 Jan; 11(?):10. doi:
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Turkish neurosurgery.
2010 Jan; 20(1):57-62. doi:
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Neurologia medico-chirurgica.
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The Journal of biological chemistry.
2009 Nov; 284(48):33535-48. doi:
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Journal of lipid research.
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