2'-Deoxyuridine 5'-monophosphate disodium salt (BioDeep_00000001602)
Secondary id: BioDeep_00000400397, BioDeep_00000406128
natural product human metabolite PANOMIX_OTCML-2023 Endogenous BioNovoGene_Lab2019
代谢物信息卡片
化学式: C9H13N2O8P (308.0409508)
中文名称: 2-脱氧胸苷-5-三磷酸三钠二水, 2-脱氧尿嘧啶核苷-5'-单磷酸, 脱氧尿苷酸, 2'-脱氧尿苷-5'-单磷酸(DUMP)
谱图信息:
最多检出来源 Homo sapiens(plant) 12.66%
Last reviewed on 2024-09-14.
Cite this Page
2'-Deoxyuridine 5'-monophosphate disodium salt. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/2_-deoxyuridine_5_-monophosphate_disodium_salt (retrieved
2024-12-04) (BioDeep RN: BioDeep_00000001602). 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(=O)NC2=O)COP(=O)(O)O)O
InChI: InChI=1S/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
描述信息
Deoxyuridine monophosphate (dUMP), also known as deoxyuridylic acid or deoxyuridylate in its conjugate acid and conjugate base forms, respectively, is a deoxynucleotide. It 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. dUMP exists in all living species, ranging from bacteria to humans. Within humans, dUMP participates in a number of enzymatic reactions. In particular, dUMP can be biosynthesized from dCMP through its interaction with the enzyme deoxycytidylate deaminase. In addition, dUMP can be biosynthesized from deoxyuridine; which is mediated by the enzyme thymidine kinase, cytosolic. In humans, dUMP is involved in pyrimidine metabolism. A pyrimidine 2-deoxyribonucleoside 5-monophosphate having uracil as the nucleobase. Outside of the human body, dUMP has been detected, but not quantified in several different foods, such as breadnut tree seeds, sea-buckthornberries, sour cherries, black walnuts, and common oregano.
dUMP is formed by the reduction of ribonucleotides to deoxyribonucleotides by ribonucleoside diphosphate reductase [EC 1.17.4.1]. dUMP by the action of by thymidylate synthetase [EC 2.1.1.45] produces dTMP (5,10-Methylene-5,6,7,8-tetrahydrofolate is a cofactor for the reaction). The nuclear form of uracil-DNA glycosylase (UNG2), that its major role is to remove misincorporated dUMP residues (cells deficient in removal of misincorporated dUMP accumulate uracil residues). (PMID 11554311) [HMDB]. dUMP is found in many foods, some of which are ginger, evergreen huckleberry, vanilla, and common walnut.
dUMP. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=964-26-1 (retrieved 2024-07-15) (CAS RN: 964-26-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
同义名列表
27 个代谢物同义名
{[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid; 2-Deoxyuridine-5-monophosphate disodium salt; 2-Deoxyuridine 5-monophosphate (dUMP); 2-Deoxyuridine 5-monophosphoric acid; 2-Deoxyuridylic acid, disodium salt; Deoxyuridine monophosphate (dUMP); 2-Deoxyuridine 5-phosphoric acid; Deoxyuridine monophosphoric acid; 2-Deoxyuridine-5-monophosphate; Deoxyuridine 5-phosphoric acid; 2-Deoxyuridine 5-monophosphate; Deoxyuridine 5-monophosphate; 2-Deoxyuridine 5-phosphate; Deoxyuridine monophosphate; Deoxyuridine 5-phosphate; 2-Deoxy-5-uridylic acid; 2-Deoxyuridylic acid; 2-Deoxy-5-uridylate; Deoxyuridylic acid; 2-Deoxyuridylate; SCHEMBL21941035; Deoxyuridylate; Deoxy-UMP; dUMP; 2'-Deoxyuridine 5'-phosphate(dUMP); dUMP; 2'-Deoxyuridine 5'-monophosphate
数据库引用编号
34 个数据库交叉引用编号
- ChEBI: CHEBI:17622
- KEGG: C00365
- PubChem: 65063
- PubChem: 688
- HMDB: HMDB0001409
- Metlin: METLIN3440
- Metlin: METLIN4140
- DrugBank: DB03800
- ChEMBL: CHEMBL211312
- Wikipedia: Deoxyuridine_monophosphate
- MetaCyc: DUMP
- KNApSAcK: C00019282
- foodb: FDB022604
- chemspider: 58574
- CAS: 964-26-1
- MoNA: PS015104
- MoNA: PS015103
- MoNA: PS015107
- MoNA: PS015102
- MoNA: PR100526
- MoNA: PS015108
- MoNA: PS015105
- MoNA: PS015101
- MoNA: PS015109
- MoNA: PS015106
- PMhub: MS000000838
- PDB-CCD: DU
- PDB-CCD: UMP
- 3DMET: B01231
- NIKKAJI: J298.569A
- RefMet: dUMP
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-232
- PubChem: 3656
- KNApSAcK: 17622
分类词条
相关代谢途径
Reactome(0)
BioCyc(4)
PlantCyc(0)
代谢反应
53 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(11)
- folate metabolism:
H+ + ser + tetrahydrofolate ⟶ 5,10-methylene-THF + H2O + gly
- pyrimidine deoxyribonucleotides de novo biosynthesis I:
H2O + dCTP ⟶ ammonia + dUTP
- salvage pathways of pyrimidine deoxyribonucleotides:
H2O + deoxycytidine ⟶ ammonia + deoxyuridine
- purine and pyrimidine metabolism:
adenosine + phosphate ⟶ α-D-ribose-1-phosphate + adenine
- pyrimidine deoxyribonucleotides de novo biosynthesis I:
H2O + dCTP ⟶ ammonia + dUTP
- formylTHF biosynthesis II:
H+ + NAD+ + gly + tetrahydrofolate ⟶ 5,10-methylenetetrahydrofolate + CO2 + NADH + ammonia
- formylTHF biosynthesis I:
H+ + NAD+ + gly + tetrahydrofolate ⟶ 5,10-methylenetetrahydrofolate + CO2 + NADH + ammonia
- salvage pathways of pyrimidine deoxyribonucleotides:
ATP + deoxyuridine ⟶ ADP + H+ + dUMP
- folate transformations II:
L-serine + a tetrahydrofolate ⟶ H2O + a 5,10-methylenetetrahydrofolate + glycine
- salvage pathways of pyrimidine deoxyribonucleotides:
H2O + deoxycytidine ⟶ ammonia + deoxyuridine
- pyrimidine deoxyribonucleotides de novo biosynthesis:
H2O + dCTP ⟶ ammonia + dUTP
WikiPathways(3)
- One-carbon metabolism:
dUMP ⟶ dTMP
- Fluoropyrimidine activity:
Capecitabine ⟶ 5-dFCR
- Fluoropyrimidine activity:
Capecitabine ⟶ 5-dFCR
Plant Reactome(0)
INOH(3)
- ATP + dUMP = ADP + dUDP ( Pyrimidine Nucleotides and Nucleosides metabolism ):
ADP + dUDP ⟶ ATP + dUMP
- Pyrimidine Nucleotides and Nucleosides metabolism ( Pyrimidine Nucleotides and Nucleosides metabolism ):
Deoxy-cytidine + H2O ⟶ Deoxy-uridine + NH3
- Folate metabolism ( Folate metabolism ):
6-Pyruvoyl-5,6,7,8-tetrahydro-pterin + NADPH ⟶ 5,6,7,8-Tetrahydro-biopterin + NADP+
PlantCyc(0)
PathBank(26)
- MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Pyrimidine Metabolism:
Hydrogen Ion + N-carbamoyl-L-aspartate ⟶ 4,5-Dihydroorotic acid + Water
- One Carbon Pool by Folate:
S-Aminomethyldihydrolipoylprotein; + Tetrahydrofolic acid ⟶ 5,10-Methylene-THF + Ammonia + dihydrolipoylprotein
- Salvage Pathways of Pyrimidine Deoxyribonucleotides:
Deoxycytidine + Hydrogen Ion + Water ⟶ Ammonium + Deoxyuridine
- One Carbon Pool by Folate I:
S-Aminomethyldihydrolipoylprotein; + Tetrahydrofolic acid ⟶ 5,10-Methylene-THF + Ammonia + dihydrolipoylprotein
- Pyrimidine Metabolism:
Hydrogen Ion + N-carbamoyl-L-aspartate ⟶ 4,5-Dihydroorotic acid + Water
- 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
- UMP Synthase Deficiency (Orotic Aciduria):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- beta-Ureidopropionase Deficiency:
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
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Dihydropyrimidinase 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:
Hydrogen Ion + N-carbamoyl-L-aspartate ⟶ 4,5-Dihydroorotic acid + Water
- One Carbon Pool by Folate:
S-Aminomethyldihydrolipoylprotein; + Tetrahydrofolic acid ⟶ 5,10-Methylene-THF + Ammonia + dihydrolipoylprotein
- beta-Ureidopropionase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
PharmGKB(0)
2 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
- Lv Gang, Li Jun, Li Yexin, Wang Ting, Liu Yazhuo, Fu Xinyang. Preferential flow characteristics of reclaimed mine soils in a surface coal mine dump.
Environmental monitoring and assessment.
2017 Jun; 189(6):266. doi:
10.1007/s10661-017-5977-4
. [PMID: 28497296] - Anamika Kushwaha, Radha Rani, Sanjay Kumar, Tarence Thomas, Arun Alfred David, Meraz Ahmed. A new insight to adsorption and accumulation of high lead concentration by exopolymer and whole cells of lead-resistant bacterium Acinetobacter junii L. Pb1 isolated from coal mine dump.
Environmental science and pollution research international.
2017 Apr; 24(11):10652-10661. doi:
10.1007/s11356-017-8752-8
. [PMID: 28283975] - Lucia Grumetto, Giovanni Ortosecco, Giacomo Russo, Maurizio Guida, Pasquale Ferranti, Antonella Nasi, Francesco Barbato. Dioxin-like PCB levels in maternal and umbilical cord sera of people living near dump sites in southern Italy: a pilot study of biomonitoring.
Environmental monitoring and assessment.
2015 Mar; 187(3):88. doi:
10.1007/s10661-015-4267-2
. [PMID: 25663396] - Glenn Tisman, April Garcia. Control of prostate cancer associated with withdrawal of a supplement containing folic acid, L-methyltetrahydrofolate and vitamin B12: a case report.
Journal of medical case reports.
2011 Aug; 5(?):413. doi:
10.1186/1752-1947-5-413
. [PMID: 21867542] - Emeline Dubois, Dolores Córdoba-Cañero, Sophie Massot, Nicolas Siaud, Bertrand Gakière, Séverine Domenichini, Florence Guérard, Teresa Roldan-Arjona, Marie-Pascale Doutriaux. Homologous recombination is stimulated by a decrease in dUTPase in Arabidopsis.
PloS one.
2011 Apr; 6(4):e18658. doi:
10.1371/journal.pone.0018658
. [PMID: 21541310] - Vikki Ho, Thomas E Massey, Will D King. Influence of thymidylate synthase gene polymorphisms on total plasma homocysteine concentrations.
Molecular genetics and metabolism.
2010 Sep; 101(1):18-24. doi:
10.1016/j.ymgme.2010.05.010
. [PMID: 20580582] - Fabio Coppedè. One-carbon metabolism and Alzheimer's disease: focus on epigenetics.
Current genomics.
2010 Jun; 11(4):246-60. doi:
10.2174/138920210791233090
. [PMID: 21119889] - Bunzo Nakata, Ryosuke Amano, Shigetomi Nakao, Tatsuro Tamura, Osamu Shinto, Toshiki Hirakawa, Yoshihiro Okita, Nobuya Yamada, Kosei Hirakawa. Plasma pharmacokinetics after combined therapy of gemcitabine and oral S-1 for unresectable pancreatic cancer.
Journal of experimental & clinical cancer research : CR.
2010 Feb; 29(?):15. doi:
10.1186/1756-9966-29-15
. [PMID: 20181235] - Golo Kronenberg, Christoph Harms, Robert W Sobol, Fernando Cardozo-Pelaez, Heinz Linhart, Benjamin Winter, Mustafa Balkaya, Karen Gertz, Shanna B Gay, David Cox, Sarah Eckart, Michael Ahmadi, Georg Juckel, Gerd Kempermann, Rainer Hellweg, Reinhard Sohr, Heide Hörtnagl, Samuel H Wilson, Rudolf Jaenisch, Matthias Endres. Folate deficiency induces neurodegeneration and brain dysfunction in mice lacking uracil DNA glycosylase.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2008 Jul; 28(28):7219-30. doi:
10.1523/jneurosci.0940-08.2008
. [PMID: 18614692] - Janee Gelineau-van Waes, Joyce R Maddox, Lynette M Smith, Michael van Waes, Justin Wilberding, James D Eudy, Linda K Bauer, Richard H Finnell. Microarray analysis of E9.5 reduced folate carrier (RFC1; Slc19a1) knockout embryos reveals altered expression of genes in the cubilin-megalin multiligand endocytic receptor complex.
BMC genomics.
2008 Apr; 9(?):156. doi:
10.1186/1471-2164-9-156
. [PMID: 18400109] - 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] - Simon Itou, Yasuyuki Goto, Takaaki Kondo, Kazuko Nishio, Sayo Kawai, Yoshiko Ishida, Mariko Naito, Nobuyuki Hamajima. No associations of Helicobacter pylori infection and gastric atrophy with plasma total homocysteine in Japanese.
International journal of medical sciences.
2007 Mar; 4(2):98-104. doi:
10.7150/ijms.4.98
. [PMID: 17396161] - R Sharma, L Rivory, P Beale, S Ong, L Horvath, S J Clarke. A phase II study of fixed-dose capecitabine and assessment of predictors of toxicity in patients with advanced/metastatic colorectal cancer.
British journal of cancer.
2006 Apr; 94(7):964-8. doi:
10.1038/sj.bjc.6603049
. [PMID: 16552436] - Priyanka Sharma, R D Senthilkumar, Vani Brahmachari, Elayanambi Sundaramoorthy, Anubha Mahajan, Amitabh Sharma, Shantanu Sengupta. Mining literature for a comprehensive pathway analysis: a case study for retrieval of homocysteine related genes for genetic and epigenetic studies.
Lipids in health and disease.
2006 Jan; 5(?):1. doi:
10.1186/1476-511x-5-1
. [PMID: 16430779] - Wen Tan, Xiaoping Miao, Li Wang, Chunyuan Yu, Ping Xiong, Gang Liang, Tong Sun, Yifeng Zhou, Xuemei Zhang, Hui Li, Dongxin Lin. Significant increase in risk of gastroesophageal cancer is associated with interaction between promoter polymorphisms in thymidylate synthase and serum folate status.
Carcinogenesis.
2005 Aug; 26(8):1430-5. doi:
10.1093/carcin/bgi090
. [PMID: 15817609] - Susan Pratt, Robert L Shepard, Ramani A Kandasamy, Paul A Johnston, William Perry, Anne H Dantzig. The multidrug resistance protein 5 (ABCC5) confers resistance to 5-fluorouracil and transports its monophosphorylated metabolites.
Molecular cancer therapeutics.
2005 May; 4(5):855-63. doi:
10.1158/1535-7163.mct-04-0291
. [PMID: 15897250] - Binh N Trinh, Choon-Nam Ong, Gerhard A Coetzee, Mimi C Yu, Peter W Laird. Thymidylate synthase: a novel genetic determinant of plasma homocysteine and folate levels.
Human genetics.
2002 Sep; 111(3):299-302. doi:
10.1007/s00439-002-0779-2
. [PMID: 12215845] - L M Iyer, L Aravind, P Bork, K Hofmann, A R Mushegian, I B Zhulin, E V Koonin. Quod erat demonstrandum? The mystery of experimental validation of apparently erroneous computational analyses of protein sequences.
Genome biology.
2001; 2(12):RESEARCH0051. doi:
10.1186/gb-2001-2-12-research0051
. [PMID: 11790254] - C Rampazzo, L Gallinaro, E Milanesi, E Frigimelica, P Reichard, V Bianchi. A deoxyribonucleotidase in mitochondria: involvement in regulation of dNTP pools and possible link to genetic disease.
Proceedings of the National Academy of Sciences of the United States of America.
2000 Jul; 97(15):8239-44. doi:
10.1073/pnas.97.15.8239
. [PMID: 10899995] - E G Pardo, P Hernández, C Gutiérrez. The incorporation of deoxyuridine monophosphate into DNA increases the sister-chromatid exchange yield.
Experimental cell research.
1987 Feb; 168(2):507-17. doi:
10.1016/0014-4827(87)90023-1
. [PMID: 2948827] - R G Richards, O E Brown, W D Sedwick. Misincorporation of deoxyuridine in human cells: consequences of antifolate exposure.
Basic life sciences.
1985; 31(?):149-62. doi:
10.1007/978-1-4613-2449-2_9
. [PMID: 3873237] - A L Sheffer, D T Fearon, K F Austen. Methyltestosterone therapy in hereditary angioedema.
Annals of internal medicine.
1977 Mar; 86(3):306-8. doi:
10.7326/0003-4819-86-3-306
. [PMID: 320930] - S Husted, T Hjort. Sperm antibodies in serum and seminal plasma.
International journal of fertility.
1975; 20(2):97-105. doi:
NULL
. [PMID: 3485]