Uracil (BioDeep_00000002133)

 

Secondary id: BioDeep_00000400033, BioDeep_00000860824

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Chemicals and Drugs Antitumor activity BioNovoGene_Lab2019


代谢物信息卡片


1,2,3,4-tetrahydropyrimidine-2,4-dione

化学式: C4H4N2O2 (112.0273)
中文名称: 尿嘧啶
谱图信息: 最多检出来源 Homo sapiens(plant) 12.04%

Reviewed

Last reviewed on 2024-07-01.

Cite this Page

Uracil. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/uracil (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000002133). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CNC(=O)NC1=O
InChI: InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)

描述信息

Uracil, also known as U, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Uracil is a common naturally occurring pyrimidine found in RNA. It base pairs with adenine and is replaced by thymine in DNA. Uracil is one of the four nucleobases in RNA that are represented by the letters A, G, C and U. Methylation of uracil produces thymine. The name "uracil" was coined in 1885 by the German chemist Robert Behrend, who was attempting to synthesize derivatives of uric acid. Originally discovered in 1900, uracil was isolated by hydrolysis of yeast nuclein that was found in bovine thymus and spleen, herring sperm, and wheat germ. Uracil exists in all living species, ranging from bacteria to plants to humans. Uracils use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as an allosteric regulator and a coenzyme for many important biochemical reactions. Uracil (via the nucleoside uridine) can be phosphorylated by various kinases to produce UMP, UDP and UTP. UDP and UTP regulate carbamoyl phosphate synthetase II (CPSase II) activity in animals. Uracil is also involved in the biosynthesis of polysaccharides and in the transport of sugars containing aldehydes. Within humans, uracil participates in a number of enzymatic reactions. In particular, uracil and ribose 1-phosphate can be biosynthesized from uridine; which is mediated by the enzyme uridine phosphorylase 2. In addition, uracil can be converted into dihydrouracil through the action of the enzyme dihydropyrimidine dehydrogenase [NADP(+)]. Uracil is rarely found in DNA, and this may have been an evolutionary change to increase genetic stability. This is because cytosine can deaminate spontaneously to produce uracil through hydrolytic deamination. Therefore, if there were an organism that used uracil in its DNA, the deamination of cytosine (which undergoes base pairing with guanine) would lead to formation of uracil (which would base pair with adenine) during DNA synthesis. Uracil can be used for drug delivery and as a pharmaceutical. When elemental fluorine reacts with uracil, it produces 5-fluorouracil. 5-Fluorouracil is an anticancer drug (antimetabolite) that mimics uracil during the nucleic acid (i.e. RNA) synthesis and transcription process. Because 5-fluorouracil is similar in shape to, but does not undergo the same chemistry as, uracil, the drug inhibits RNA replication enzymes, thereby blocking RNA synthesis and stopping the growth of cancerous cells.
Uracil is a common and naturally occurring pyrimidine derivative. Originally discovered in 1900, it was isolated by hydrolysis of yeast nuclein that was found in bovine thymus and spleen, herring sperm, and wheat germ. It is a planar, unsaturated compound that has the ability to absorb light.

Uracil. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=66-22-8 (retrieved 2024-07-01) (CAS RN: 66-22-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA.
Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA.
Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA.

同义名列表

17 个代谢物同义名

1,2,3,4-tetrahydropyrimidine-2,4-dione; 2,4(1H,3H)-Pyrimidinedione; 2,4-Dihydroxypyrimidine; 2,4-Pyrimidinedione; 2,4-Dioxopyrimidine; 2,4-Pyrimidinediol; Uracil-5-d; Hybar X; Urazil; Uracil; Pirod; Pyrod; Ura; u; Uracil; Uracil; Uracil



数据库引用编号

35 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(6)

BioCyc(20)

PlantCyc(3)

代谢反应

1341 个相关的代谢反应过程信息。

Reactome(183)

BioCyc(227)

WikiPathways(4)

Plant Reactome(4)

INOH(4)

PlantCyc(880)

COVID-19 Disease Map(1)

PathBank(38)

PharmGKB(0)

86 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。

亚细胞结构定位 关联基因列表
Cytoplasm 7 APOB, APOBEC3G, DPYD, PMP2, POLB, PSMA1, TP53
Endosome membrane 1 APOB
Endoplasmic reticulum membrane 1 APOB
Nucleus 13 APOBEC3G, DUT, LIG4, MBD4, MSH2, MSH6, PCNA, PMP2, POLB, PSMA1, SMUG1, TDG, TP53
cytosol 12 APOB, APOBEC3G, CDA, DPYD, MSH6, MTHFR, PMP2, PSMA1, SMUG1, TP53, TYMP, UPP1
nuclear body 1 PCNA
centrosome 3 PCNA, PSMA1, TP53
nucleoplasm 12 DUT, LIG4, MBD4, MSH2, MSH6, PCNA, POLB, PSMA1, SMUG1, TDG, TP53, UPP1
Golgi apparatus 1 MSH6
mitochondrial inner membrane 1 OTC
neuronal cell body 1 APOB
smooth endoplasmic reticulum 1 APOB
plasma membrane 2 APOB, TDG
Membrane 2 MSH2, TP53
extracellular exosome 5 APOB, DUT, PCNA, PMP2, PSMA1
endoplasmic reticulum 1 TP53
extracellular space 1 APOB
lysosomal lumen 1 APOB
mitochondrion 3 DUT, OTC, TP53
protein-containing complex 2 POLB, TP53
intracellular membrane-bounded organelle 3 APOB, LIG4, MSH6
Secreted 1 APOB
extracellular region 2 APOB, CDA
Mitochondrion matrix 2 OTC, TP53
mitochondrial matrix 2 OTC, TP53
transcription regulator complex 1 TP53
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
chylomicron 1 APOB
low-density lipoprotein particle 1 APOB
very-low-density lipoprotein particle 1 APOB
nucleolus 2 SMUG1, TP53
Cytoplasm, P-body 1 APOBEC3G
P-body 1 APOBEC3G
Early endosome 1 APOB
Cytoplasm, cytoskeleton 1 TP53
microtubule 1 POLB
Nucleus, PML body 1 TP53
PML body 2 TDG, TP53
nuclear speck 1 MBD4
apolipoprotein B mRNA editing enzyme complex 1 APOBEC3G
chromatin 3 MSH6, PCNA, TP53
Chromosome 2 MSH2, MSH6
nuclear replication fork 1 PCNA
chromosome, telomeric region 3 LIG4, MSH2, PCNA
site of double-strand break 1 TP53
fibrillar center 1 SMUG1
endosome lumen 1 APOB
Lipid droplet 1 APOB
germ cell nucleus 1 TP53
replication fork 2 PCNA, TP53
myelin sheath 1 PMP2
ficolin-1-rich granule lumen 1 CDA
proteasome complex 1 PSMA1
secretory granule lumen 1 CDA
endoplasmic reticulum lumen 1 APOB
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
male germ cell nucleus 1 PCNA
tertiary granule lumen 1 CDA
endoplasmic reticulum exit site 1 APOB
proteasome core complex 1 PSMA1
proteasome core complex, alpha-subunit complex 1 PSMA1
nuclear lamina 1 PCNA
clathrin-coated endocytic vesicle membrane 1 APOB
ribonucleoprotein complex 1 APOBEC3G
[Isoform 2]: Nucleus 1 DUT
[Isoform 1]: Nucleus 1 TP53
spindle microtubule 1 POLB
condensed chromosome 1 LIG4
[Isoform 3]: Mitochondrion 1 DUT
cyclin-dependent protein kinase holoenzyme complex 1 PCNA
endocytic vesicle lumen 1 APOB
chylomicron remnant 1 APOB
intermediate-density lipoprotein particle 1 APOB
mature chylomicron 1 APOB
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
DNA-dependent protein kinase-DNA ligase 4 complex 1 LIG4
nonhomologous end joining complex 1 LIG4
MutSbeta complex 1 MSH2
MutSalpha complex 2 MSH2, MSH6
DNA ligase IV complex 1 LIG4


文献列表

  • Yaning Wu, Hongwei Zhang, Jianguang Zhu, Zhenling Zhang, Songbo Ma, Yongqi Zhao, Yiming Wang, Jun Yuan, Xing Guo, Yajing Li, Shuai Zhang. The Effect of Fermentation on the Chemical Constituents of Gastrodia Tuber Hallimasch Powder (GTHP) Estimated by UHPLC-Q-Orbitrap HRMS and HPLC. Molecules (Basel, Switzerland). 2024 Apr; 29(7):. doi: 10.3390/molecules29071663. [PMID: 38611942]
  • Di-Zao Li, Zhao-Di Fu, Hong-Yan Liu, Xian-Dao Pan. Facile synthesis and cytotoxicity of substituted uracil-1'(N)-acetic acid and 4-pyridone-1'(N)-acetic acid esters of 20(S)-camptothecins. Journal of Asian natural products research. 2024 Feb; 26(2):259-268. doi: 10.1080/10286020.2023.2300374. [PMID: 38347748]
  • Huan Zhou, Qing X Li, Lei Zeng, Congwang Cao, Tuotuo Zhang, Yuan Zhou, Hongwu He. Uracil hydrazones: design, synthesis, antimicrobial activities, and putative mode of action. Pest management science. 2023 Sep; ?(?):. doi: 10.1002/ps.7771. [PMID: 37708309]
  • Kevin Xiao, Homa Ghalei, Sohail Khoshnevis. RNA structural probing of guanine and uracil nucleotides in yeast. PloS one. 2023; 18(7):e0288070. doi: 10.1371/journal.pone.0288070. [PMID: 37418367]
  • Alexey A Chistov, Stepan P Chumakov, Igor E Mikhnovets, Timofei D Nikitin, Nikita A Slesarchuk, Victoria I Uvarova, Anna A Rubekina, Yulia V Nikolaeva, Eugene V Radchenko, Evgeny V Khvatov, Alexey A Orlov, Vasilisa S Frolenko, Maksim V Sukhorukov, Ekaterina S Kolpakova, Elena Y Shustova, Anastasiya V Galochkina, Philipp P Streshnev, Eugene M Osipov, Ksenia A Sapozhnikova, Andrey V Moiseenko, Vladimir A Brylev, Gleb V Proskurin, Yuri S Dokukin, Sergey V Kutyakov, Andrey V Aralov, Vladimir A Korshun, Sergei V Strelkov, Vladimir A Palyulin, Aydar A Ishmukhametov, Evgeny A Shirshin, Dmitry I Osolodkin, Anna A Shtro, Liubov I Kozlovskaya, Vera A Alferova, Alexey V Ustinov. 5-(Perylen-3-ylethynyl)uracil as an antiviral scaffold: Potent suppression of enveloped virus reproduction by 3-methyl derivatives in vitro. Antiviral research. 2023 01; 209(?):105508. doi: 10.1016/j.antiviral.2022.105508. [PMID: 36581049]
  • Lai Wong, Alina Sami, Linda Chelico. Competition for DNA binding between the genome protector replication protein A and the genome modifying APOBEC3 single-stranded DNA deaminases. Nucleic acids research. 2022 11; 50(21):12039-12057. doi: 10.1093/nar/gkac1121. [PMID: 36444883]
  • Tahmineh Peirouvi, Mazdak Razi. Molecular mechanism behind methamphetamine-induced damages in testicular tissue: Evidences for oxidative stress, autophagy, and apoptosis. Andrologia. 2022 Nov; 54(10):e14534. doi: 10.1111/and.14534. [PMID: 35801363]
  • Chenchen Ma, Peng Liu, Siyuan Cui, Chang Gao, Xing Tan, Zhaopeng Liu, Ruirong Xu. The Identification of APOBEC3G as a Potential Prognostic Biomarker in Acute Myeloid Leukemia and a Possible Drug Target for Crotonoside. Molecules (Basel, Switzerland). 2022 Sep; 27(18):. doi: 10.3390/molecules27185804. [PMID: 36144542]
  • Hae Jin Kim, In Kyung Jeong, Kyu Yeon Hur, Soo-Kyung Kim, Jung Hyun Noh, Sung Wan Chun, Eun Seok Kang, Eun-Jung Rhee, Sung Hee Choi. Comparison of Efficacy of Glimepiride, Alogliptin, and Alogliptin-Pioglitazone as the Initial Periods of Therapy in Patients with Poorly Controlled Type 2 Diabetes Mellitus: An Open-Label, Multicenter, Randomized, Controlled Study. Diabetes & metabolism journal. 2022 09; 46(5):689-700. doi: 10.4093/dmj.2021.0183. [PMID: 35295073]
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  • Xenia Bacinschi, Gabriel Cristian Popescu, Anca Zgura, Laurentia Gales, Anghel Rodica, Adriana Mercan, Dragos Serban, Bogdan Haineala, Letitia Toma, Laura Iliescu. A Real-World Study to Compare the Safety and Efficacy of Paritaprevir/Ombitasvir/Ritonavir and Dasabuvir, with or without Ribavirin, in 587 Patients with Chronic Hepatitis C at the Fundeni Clinical Institute, Bucharest, Romania. Medical science monitor : international medical journal of experimental and clinical research. 2022 Jul; 28(?):e936706. doi: 10.12659/msm.936706. [PMID: 35787600]
  • Mirjam de With, Jonathan Knikman, Femke M de Man, Carin A T C Lunenburg, Linda M Henricks, André B P van Kuilenburg, Jan G Maring, Maurice C van Staveren, Niels de Vries, Hilde Rosing, Jos H Beijnen, Dick Pluim, Anil Modak, Alex L T Imholz, Ron H N van Schaik, Jan H M Schellens, Hans Gelderblom, Annemieke Cats, Henk-Jan Guchelaar, Ron H J Mathijssen, Jesse J Swen, Didier Meulendijks. Dihydropyrimidine Dehydrogenase Phenotyping Using Pretreatment Uracil: A Note of Caution Based on a Large Prospective Clinical Study. Clinical pharmacology and therapeutics. 2022 07; 112(1):62-68. doi: 10.1002/cpt.2608. [PMID: 35397172]
  • Beatrice Campanella, Tommaso Lomonaco, Edoardo Benedetti, Massimo Onor, Riccardo Nieri, Federica Marmorino, Chiara Cremolini, Emilia Bramanti. Fast, Direct Dihydrouracil Quantitation in Human Saliva: Method Development, Validation, and Application. International journal of environmental research and public health. 2022 05; 19(10):. doi: 10.3390/ijerph19106033. [PMID: 35627569]
  • Xenia Bacinschi, Adriana Mercan-Stanciu, Letitia Toma, Anca Zgura, Nicolae Bacalbasa, Chen-Peng Ifrim, Camelia Diaconu, Laura Iliescu, Radu Valeriu Toma. Glycemic Control in Patients Undergoing Treatment With Paritaprevir/Ombitasvir/Ritonavir and Dasabuvir for Chronic Hepatitis C Infection. In vivo (Athens, Greece). 2022 May; 36(3):1438-1443. doi: 10.21873/invivo.12849. [PMID: 35478152]
  • Hikari Araki, Toru Takenaka, Koichi Takahashi, Fumiaki Yamashita, Kazuaki Matsuoka, Kunihiro Yoshisue, Ichiro Ieiri. A semimechanistic population pharmacokinetic and pharmacodynamic model incorporating autoinduction for the dose justification of TAS-114. CPT: pharmacometrics & systems pharmacology. 2022 05; 11(5):604-615. doi: 10.1002/psp4.12747. [PMID: 34951129]
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  • Sara Capiau, Anniek Van Landschoot, Tim Reyns, Hedwig Stepman. Pre-analytical considerations for the analysis of uracil and 5,6-dihydrouracil in heparin plasma. Clinical chemistry and laboratory medicine. 2022 04; 60(5):e112-e115. doi: 10.1515/cclm-2021-0921. [PMID: 35073467]
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  • Deep Dutta, Ritin Mohindra, Vineet Surana, Meha Sharma. Safety and efficacy of once weekly dipeptidyl-peptidase-4 inhibitor trelagliptin in type-2 diabetes: A meta-analysis. Diabetes & metabolic syndrome. 2022 Apr; 16(4):102469. doi: 10.1016/j.dsx.2022.102469. [PMID: 35344848]
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  • Beatriz Chamorro, Iwona E Głowacka, Joanna Gotkowska, Rafał Gulej, Dimitra Hadjipavlou-Litina, Francisco López-Muñoz, José Marco-Contelles, Dorota G Piotrowska, María Jesús Oset-Gasque. Nucleobase-Derived Nitrones: Synthesis and Antioxidant and Neuroprotective Activities in an In Vitro Model of Ischemia-Reperfusion. International journal of molecular sciences. 2022 Mar; 23(6):. doi: 10.3390/ijms23063411. [PMID: 35328832]
  • Marcel Schneider, Marina F Grossi, Darshak Gadara, Zdeněk Spáčil, Pavel Babica, Luděk Bláha. Treatment of cylindrospermopsin by hydroxyl and sulfate radicals: Does degradation equal detoxification?. Journal of hazardous materials. 2022 02; 424(Pt B):127447. doi: 10.1016/j.jhazmat.2021.127447. [PMID: 34688008]
  • Ke Feng, Wenjie Dai, Ling Liu, Shengming Li, Yi Gou, Zhongwei Chen, Guodong Chen, Xufeng Fu. Identification of biomarkers and the mechanisms of multiple trauma complicated with sepsis using metabolomics. Frontiers in public health. 2022; 10(?):923170. doi: 10.3389/fpubh.2022.923170. [PMID: 35991069]
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  • Yikelamu Alimu, Yoko Kusuya, Takako Yamamoto, Kana Arita, Naofumi Shigemune, Hiroki Takahashi, Takashi Yaguchi. Mechanism of Polyhexamethylene Biguanide Resistance in Purpureocillium lilacinum Strains. Biocontrol science. 2022; 27(3):117-130. doi: 10.4265/bio.27.117. [PMID: 36216563]
  • Tsuyoshi Hayashi, Kosuke Murakami, Junki Hirano, Yoshiki Fujii, Yoko Yamaoka, Hirofumi Ohashi, Koichi Watashi, Mary K Estes, Masamichi Muramatsu. Dasabuvir Inhibits Human Norovirus Infection in Human Intestinal Enteroids. mSphere. 2021 12; 6(6):e0062321. doi: 10.1128/msphere.00623-21. [PMID: 34730374]
  • Li-Qing Xu, Li-Jie Yao, Dan Jiang, Li-Juan Zhou, Min Chen, Wen-Zhong Liao, Wei-Hao Zou, Hong-Juan Peng. A uracil auxotroph Toxoplasma gondii exerting immunomodulation to inhibit breast cancer growth and metastasis. Parasites & vectors. 2021 Dec; 14(1):601. doi: 10.1186/s13071-021-05032-6. [PMID: 34895326]
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  • Clotilde Gaible, Céline Narjoz, Marie-Anne Loriot, Stéphane Roueff, Nicolas Pallet. Pretherapeutic screening for Dihydropyrimidine deshydrogenase deficiency in measuring uracilemia in dialysis patients leads to a high rate of falsely positive results. Cancer chemotherapy and pharmacology. 2021 12; 88(6):1049-1053. doi: 10.1007/s00280-021-04354-7. [PMID: 34515833]
  • Fabrizio Fabrizi, Cristina Alonso, Ana Palazzo, Margarita Anders, Maria Virginia Reggiardo, Hugo Cheinquer, Maria Grazia Videla Zuain, Sebastian Figueroa, Manuel Mendizabal, Marcelo Silva, Ezequiel Ridruejo. 'Real-life' experience with direct-acting antiviral agents for HCV after kidney transplant. Annals of hepatology. 2021 Nov; 25(?):100337. doi: 10.1016/j.aohep.2021.100337. [PMID: 33684523]
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  • Alisha Wehdnesday Bernardo Reyes, Heejin Kim, Tran Xuan Ngoc Huy, Son Hai Vu, Trang Thi Nguyen, Chang Keun Kang, Wongi Min, Hu Jang Lee, John Hwa Lee, Suk Kim. Immune-metabolic receptor GPR84 surrogate and endogenous agonists, 6-OAU and lauric acid, alter Brucella abortus 544 infection in both in vitro and in vivo systems. Microbial pathogenesis. 2021 Sep; 158(?):105079. doi: 10.1016/j.micpath.2021.105079. [PMID: 34245824]
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  • Vivian Rodriguez-Cruz, Marilyn E Morris. γ-Hydroxybutyric Acid-Ethanol Drug-Drug Interaction: Reversal of Toxicity with Monocarboxylate Transporter 1 Inhibitors. The Journal of pharmacology and experimental therapeutics. 2021 07; 378(1):42-50. doi: 10.1124/jpet.121.000566. [PMID: 33963018]
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