2'-Deoxycytidine-5'-monophosphoric acid (BioDeep_00000001207)
Secondary id: BioDeep_00000398600, BioDeep_00001868602
human metabolite PANOMIX_OTCML-2023 Endogenous Antitumor activity BioNovoGene_Lab2019
代谢物信息卡片
化学式: C9H14N3O7P (307.0569)
中文名称: 2-脱氧胞苷-5-单磷酸, 2'-脱氧胞苷-5'-单磷酸, 脱氧胞苷酸, 2'-脱氧胞苷 5'-单磷酸
谱图信息:
最多检出来源 Homo sapiens(blood) 15.27%
Last reviewed on 2024-09-14.
Cite this Page
2'-Deoxycytidine-5'-monophosphoric acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/2_-deoxycytidine-5_-monophosphoric_acid (retrieved
2024-12-22) (BioDeep RN: BioDeep_00000001207). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: C1C(C(OC1N2C=CC(=NC2=O)N)COP(=O)(O)O)O
InChI: InChI=1S/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
描述信息
Deoxycytidine monophosphate (dCMP), also known as deoxycytidylic acid or deoxycytidylate in its conjugate acid and conjugate base forms, respectively, is a deoxynucleotide, and one of the four monomers that make up DNA. In a DNA double helix, it will base pair with deoxyguanosine monophosphate. dCMP belongs to the class of organic compounds known as pyrimidine 2-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. Deficiency of the enzyme deoxycytidine kinase (EC2.7.1.74) is associated with resistance to antiviral and anticancer chemotherapeutic agents, whereas increased enzyme activity is associated with increased activation of these compounds to cytotoxic nucleoside triphosphate derivatives. dCMP exists in all living species, ranging from bacteria to humans. Within humans, dCMP participates in a number of enzymatic reactions. In particular, dCMP can be converted to dCDP by the enzyme UMP-CMP kinase 2. In addition, dCMP can be converted into deoxycytidine, which is catalyzed by the enzyme cytosolic purine 5-nucleotidase. In humans, dCMP is involved in the metabolic disorder called ump synthase deficiency (orotic aciduria). Outside of the human body, dCMP has been detected, but not quantified in several different foods, such as turnips, garlics, agaves, garden onions, and italian sweet red peppers. dCMP is a deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2-,3- or 5- positions.
Deoxycytidine (dihydrogen phosphate). A deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2-,3- or 5- positions.
2'-Deoxycytidine-5'-monophosphoric acid is an endogenous metabolite.
2'-Deoxycytidine-5'-monophosphoric acid is an endogenous metabolite.
同义名列表
26 个代谢物同义名
{[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid; [(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate; 2-Deoxycytidine-5-monophosphoric acid; 2-Deoxycytosine 5-monophosphoric acid; 2-Deoxycytidine 5-monophosphoric acid; 2-Deoxycytidine-5-monophosphorate; Deoxycytidine monophosphoric acid; Cytidine 5-(dihydrogen phosphate); 2-Deoxycytidine 5-monophosphate; 2-DEOXYCYTIDINE-5-monophosphATE; 2-Deoxycytosine 5-monophosphate; 2-DEOXYCYTIDINE-3-MONOPHOSPHATE; Deoxycytidine 5-monophosphate; monoPhosphate, deoxycytidine; 2-Deoxycytidine-5-phosphate; Deoxycytidine monophosphate; Deoxycytidine-phosphate; Acids, deoxycytidylic; Deoxycytidylic acids; Acid, deoxycytidylic; Deoxycytidylic acid; Deoxycytidylate; dCMP; 2'-Deoxycytidine 5'-monophosphate(dCMP); 2'-Deoxycytidine-5'-monophosphoric acid; dCMP
数据库引用编号
24 个数据库交叉引用编号
- ChEBI: CHEBI:15918
- KEGG: C00239
- PubChem: 13945
- HMDB: HMDB0001202
- Metlin: METLIN3439
- DrugBank: DB03798
- ChEMBL: CHEMBL374699
- Wikipedia: DCMP
- MeSH: Deoxycytidine Monophosphate
- MetaCyc: DCMP
- foodb: FDB022488
- chemspider: 13343
- CAS: 1032-65-1
- PMhub: MS000000122
- PDB-CCD: DC
- PDB-CCD: DCM
- PDB-CCD: DNR
- 3DMET: B01198
- NIKKAJI: J14.407J
- RefMet: dCMP
- medchemexpress: HY-W009216
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-66
- PubChem: 3538
- KNApSAcK: 15918
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
32 个相关的代谢反应过程信息。
Reactome(9)
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Nucleotide metabolism:
H2O + XTP ⟶ PPi + XMP
- Interconversion of nucleotide di- and triphosphates:
AMP + ATP ⟶ ADP
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Nucleotide metabolism:
H2O + XTP ⟶ PPi + XMP
- Interconversion of nucleotide di- and triphosphates:
AMP + ATP ⟶ ADP
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Nucleotide metabolism:
H2O + XTP ⟶ PPi + XMP
- Interconversion of nucleotide di- and triphosphates:
AMP + ATP ⟶ ADP
BioCyc(1)
- salvage pathways of pyrimidine deoxyribonucleotides:
H2O + deoxycytidine ⟶ ammonia + deoxyuridine
Plant Reactome(0)
INOH(2)
- Pyrimidine Nucleotides and Nucleosides metabolism ( Pyrimidine Nucleotides and Nucleosides metabolism ):
Deoxy-cytidine + H2O ⟶ Deoxy-uridine + NH3
- ATP + dCMP = ADP + dCDP ( Pyrimidine Nucleotides and Nucleosides metabolism ):
ADP + dCDP ⟶ ATP + dCMP
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(19)
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- beta-Ureidopropionase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- UMP Synthase Deficiency (Orotic Aciduria):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Dihydropyrimidinase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Pyrimidine Deoxyribonucleosides Salvage:
Deoxycytidine + Hydrogen Ion + Water ⟶ Ammonium + Deoxyuridine
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- beta-Ureidopropionase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Dihydropyrimidinase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- UMP Synthase Deficiency (Orotic Aciduria):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- beta-Ureidopropionase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Dihydropyrimidinase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- UMP Synthase Deficiency (Orotic Aciduria):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
PharmGKB(0)
8 个相关的物种来源信息
- 7461 - Apis cerana: 10.1371/JOURNAL.PONE.0175573
- 3702 - Arabidopsis thaliana: 10.1074/JBC.RA118.003351
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
- 5665 - Leishmania mexicana: 10.1016/J.IJPDDR.2019.05.003
- 28901 - Salmonella enterica: 10.1039/C3MB25598K
- 714518 - Ziziphus jujuba var. spinosa: 10.1016/J.CHROMA.2013.05.074
- 569774 - 金线莲: -
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
- Cheng-Hung Lee, Chia-I Tsai, Yi-Chang Su, Shih-Yi Lin, I-Te Lee, Tsai-Chung Li. Traditional Chinese medicine body constitution predicts new-onset diabetic albuminuria in patients with type 2 diabetes: Taichung diabetic body constitution prospective cohort study.
Medicine.
2022 Dec; 101(50):e32342. doi:
10.1097/md.0000000000032342
. [PMID: 36550881] - Cheng-Chieh Lin, May Jingchee Niu, Chia-Ing Li, Chiu-Shong Liu, Chih-Hsueh Lin, Shing-Yu Yang, Tsai-Chung Li. Development and validation of a risk prediction model for chronic kidney disease among individuals with type 2 diabetes.
Scientific reports.
2022 03; 12(1):4794. doi:
10.1038/s41598-022-08284-z
. [PMID: 35314714] - Akifumi Onishi, Hitoshi Sugiyama, Masashi Kitagawa, Toshio Yamanari, Keiko Tanaka, Ayu Ogawa-Akiyama, Yuzuki Kano, Koki Mise, Katsuyuki Tanabe, Hiroshi Morinaga, Masaru Kinomura, Haruhito A Uchida, Jun Wada. Urine 5MedC, a Marker of DNA Methylation, in the Progression of Chronic Kidney Disease.
Disease markers.
2019; 2019(?):5432453. doi:
10.1155/2019/5432453
. [PMID: 31354889] - Lei Han, Yongping Zhu, Min Liu, Ye Zhou, Guangyuan Lu, Lan Lan, Xianping Wang, Yongfang Zhao, Xuejun C Zhang. Molecular mechanism of substrate recognition and transport by the AtSWEET13 sugar transporter.
Proceedings of the National Academy of Sciences of the United States of America.
2017 09; 114(38):10089-10094. doi:
10.1073/pnas.1709241114
. [PMID: 28878024] - Shuo Liu, Thomas L Dunwell, Gerd P Pfeifer, Jim M Dunwell, Ihsan Ullah, Yinsheng Wang. Detection of oxidation products of 5-methyl-2'-deoxycytidine in Arabidopsis DNA.
PloS one.
2013; 8(12):e84620. doi:
10.1371/journal.pone.0084620
. [PMID: 24391970] - Jan Gerard Maring, Floris M Wachters, Monique Slijfer, J Marina Maurer, H Marike Boezen, Donald R A Uges, Elisabeth G E de Vries, Harry J M Groen. Pharmacokinetics of gemcitabine in non-small-cell lung cancer patients: impact of the 79A>C cytidine deaminase polymorphism.
European journal of clinical pharmacology.
2010 Jun; 66(6):611-7. doi:
10.1007/s00228-010-0799-0
. [PMID: 20213492] - Yukihiro Hiraoka, Hiroaki Ueda, Yukihiro Sugimoto. Molecular responses of Lotus japonicus to parasitism by the compatible species Orobanche aegyptiaca and the incompatible species Striga hermonthica.
Journal of experimental botany.
2009; 60(2):641-50. doi:
10.1093/jxb/ern316
. [PMID: 19088337] - K M Li, L P Rivory, S J Clarke. Pemetrexed pharmacokinetics and pharmacodynamics in a phase I/II study of doublet chemotherapy with vinorelbine: implications for further optimisation of pemetrexed schedules.
British journal of cancer.
2007 Oct; 97(8):1071-6. doi:
10.1038/sj.bjc.6603995
. [PMID: 17912246] - M Serova, C M Galmarini, A Ghoul, K Benhadji, S R Green, J Chiao, S Faivre, E Cvitkovic, C Le Tourneau, F Calvo, E Raymond. Antiproliferative effects of sapacitabine (CYC682), a novel 2'-deoxycytidine-derivative, in human cancer cells.
British journal of cancer.
2007 Sep; 97(5):628-36. doi:
10.1038/sj.bjc.6603896
. [PMID: 17637678] - Jian-Hong Xu, Joachim Messing. Maize haplotype with a helitron-amplified cytidine deaminase gene copy.
BMC genetics.
2006 Nov; 7(?):52. doi:
10.1186/1471-2156-7-52
. [PMID: 17094807] - C L Chen, T K Venkatachalam, Z H Zhu, F M Uckun. In vivo pharmacokinetics and metabolism of anti-human immunodeficiency virus agent D4T-5'-[p-bromophenyl methoxyalaninyl phosphate] (SAMPIDINE) in mice.
Drug metabolism and disposition: the biological fate of chemicals.
2001 Jul; 29(7):1035-41. doi:
NULL
. [PMID: 11408371] - M Tan, J Xu, Z Li, H Lei, J Zuo. [Study on GMA-DNA adducts in vivo].
Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae.
1999 Dec; 21(6):444-9. doi:
NULL
. [PMID: 12567491] - M Moriya. Single-stranded shuttle phagemid for mutagenesis studies in mammalian cells: 8-oxoguanine in DNA induces targeted G.C-->T.A transversions in simian kidney cells.
Proceedings of the National Academy of Sciences of the United States of America.
1993 Feb; 90(3):1122-6. doi:
10.1073/pnas.90.3.1122
. [PMID: 8430083] - G F Casperson, E W Voss. Specificity of anti-DNA antibodies in SLE-I. Definition and gross specificity of antibody populations in human SLE plasma.
Molecular immunology.
1983 Jun; 20(6):573-80. doi:
10.1016/0161-5890(83)90001-9
. [PMID: 6603571] - H Bannwarth, N Ikehara, H G Schweiger. Deoxycytidine monophosphate deaminase in Acetabularia: properties and regulation in the early generative phase.
European journal of cell biology.
1982 Jun; 27(2):200-5. doi:
"
. [PMID: 7117267] - W C Leung, D R Dubbs, D Trkula, S Kit. Mitochondrial and herpesvirus-specific deoxypyrimidine kinases.
Journal of virology.
1975 Sep; 16(3):486-97. doi:
10.1128/jvi.16.3.486-497.1975
. [PMID: 169387] - H A Rolton, H M Keir. Deoxycytidylate deaminase evidence for a new enzyme in cells infected by the virus of herpes simplex.
The Biochemical journal.
1974 Nov; 143(2):403-9. doi:
10.1042/bj1430403
. [PMID: 4376945] - G M Cooper. Phosphorylation of 5-bromodeoxycytidine in cells infected with herpes simplex virus.
Proceedings of the National Academy of Sciences of the United States of America.
1973 Dec; 70(12):3788-92. doi:
10.1073/pnas.70.12.3788
. [PMID: 4359489]