5,6-dihydrouracil (BioDeep_00000003090)

 

Secondary id: BioDeep_00000267406, BioDeep_00000863416

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


5,6-Dihydro-2,4(1H,3H)-pyrimidinedione

化学式: C4H6N2O2 (114.0429256)
中文名称: 二氢尿嘧啶
谱图信息: 最多检出来源 Homo sapiens(blood) 0.1%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

5,6-dihydrouracil. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/5,6-dihydrouracil (retrieved 2024-11-03) (BioDeep RN: BioDeep_00000003090). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1CNC(=O)NC1=O
InChI: InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)

描述信息

Dihydrouracil 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. Dihydrouracil is an intermediate breakdown product of uracil. Dihydrouracil exists in all living organisms, ranging from bacteria to plants to humans. Within humans, dihydrouracil participates in a number of enzymatic reactions. In particular, dihydrouracil can be biosynthesized from uracil; which is mediated by the enzyme dihydropyrimidine dehydrogenase [NADP(+)]. The breakdown of uracil is a multistep reaction that leads to the production of beta-alanine. The reaction process begins with the enzyme known as dihydropyrimidine dehydrogenase (DHP), which catalyzes the reduction of uracil into dihydrouracil. Then the enzyme known as dihydropyrimidinase hydrolyzes dihydrouracil into N-carbamyl-beta-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-beta-alanine into beta-alanine. There is at least one metabolic disorder that is associated with altered levels of dihydrouracil. In particular, dihydropyrimidinase deficiency is an inborn metabolic disorder that leads to highly increased concentrations of dihydrouracil and 5,6-dihydrothymine, and moderately increased concentrations of uracil and thymine in urine. Dihydropyrimidinase deficiency can cause neurological and gastrointestinal problems in some affected individuals (OMIM: 222748). In particular, patients with dihydropyrimidinase deficiency exhibit a number of neurological abnormalities including intellectual disability, seizures, weak muscle tone (hypotonia), an abnormally small head size (microcephaly), and autistic behaviours that affect communication and social interaction. Gastrointestinal problems that occur in dihydropyrimidinase deficiency include backflow of acidic stomach contents into the esophagus (gastroesophageal reflux) and recurrent episodes of vomiting.
3,4-dihydrouracil, also known as 2,4-dioxotetrahydropyrimidine or 5,6-dihydro-2,4-dihydroxypyrimidine, is a member of the class of 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. 3,4-dihydrouracil is soluble (in water) and a very weakly acidic compound (based on its pKa). 3,4-dihydrouracil can be found in a number of food items such as colorado pinyon, rocket salad (sspecies), wax gourd, and boysenberry, which makes 3,4-dihydrouracil a potential biomarker for the consumption of these food products. 3,4-dihydrouracil can be found primarily in blood, cerebrospinal fluid (CSF), saliva, and urine, as well as throughout most human tissues. 3,4-dihydrouracil exists in all living organisms, ranging from bacteria to humans. In humans, 3,4-dihydrouracil is involved in a couple of metabolic pathways, which include beta-alanine metabolism and pyrimidine metabolism. 3,4-dihydrouracil is also involved in several metabolic disorders, some of which include UMP synthase deficiency (orotic aciduria), dihydropyrimidinase deficiency, ureidopropionase deficiency, and carnosinuria, carnosinemia. Moreover, 3,4-dihydrouracil is found to be associated with dihydropyrimidine dehydrogenase deficiency and hypertension.
Acquisition and generation of the data is financially supported in part by CREST/JST.
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Dihydrouracil (5,6-Dihydrouracil), a metabolite of Uracil, can be used as a marker for identification of dihydropyrimidine dehydrogenase (DPD)-deficient[1][2].
Dihydrouracil (5,6-Dihydrouracil), a metabolite of Uracil, can be used as a marker for identification of dihydropyrimidine dehydrogenase (DPD)-deficient[1][2].

同义名列表

11 个代谢物同义名

5,6-Dihydro-2,4(1H,3H)-pyrimidinedione; 5,6-Dihydro-2,4-dihydroxypyrimidine; DIHYDROPYRIMIDINE-2,4(1H,3H)-dione; Dihydro-2,4(1H,3H)-pyrimidinedione; 2,4-Dioxotetrahydropyrimidine; Dihydro-pyrimidine-2,4-dione; 1,3-diazinane-2,4-dione; 5,6-Dihydrouracil; Dihydrouracile; dihydrouracil; Hydrouracil



数据库引用编号

25 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(3)

PlantCyc(0)

代谢反应

628 个相关的代谢反应过程信息。

Reactome(146)

BioCyc(21)

WikiPathways(2)

Plant Reactome(296)

INOH(3)

PlantCyc(127)

COVID-19 Disease Map(1)

PathBank(32)

PharmGKB(0)

9 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

  • 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]
  • 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]
  • Kathryn E Burns, Ottiniel Chavani, Soo Hee Jeong, John A Duley, David Porter, Michael Findlay, R Matthew Strother, Nuala A Helsby. Comparison of a thymine challenge test and endogenous uracil-dihydrouracil levels for assessment of fluoropyrimidine toxicity risk. Cancer chemotherapy and pharmacology. 2021 05; 87(5):711-716. doi: 10.1007/s00280-021-04240-2. [PMID: 33687515]
  • Nicolas Pallet, Salma Hamdane, Simon Garinet, Hélène Blons, Aziz Zaanan, Elena Paillaud, Julien Taieb, Olivier Laprevote, Marie-Anne Loriot, Céline Narjoz. A comprehensive population-based study comparing the phenotype and genotype in a pretherapeutic screen of dihydropyrimidine dehydrogenase deficiency. British journal of cancer. 2020 09; 123(5):811-818. doi: 10.1038/s41416-020-0962-z. [PMID: 32595208]
  • Clémence Marin, Anis Krache, Chloé Palmaro, Mathilde Lucas, Valentin Hilaire, Renée Ugdonne, Bénédicte De Victor, Sylvie Quaranta, Caroline Solas, Bruno Lacarelle, Joseph Ciccolini. A Simple and Rapid UPLC-UV Method for Detecting DPD Deficiency in Patients With Cancer. Clinical and translational science. 2020 07; 13(4):761-768. doi: 10.1111/cts.12762. [PMID: 32058656]
  • Xandra García-González, Bartosz Kaczmarczyk, Judith Abarca-Zabalía, Fabienne Thomas, Pilar García-Alfonso, Luis Robles, Vanessa Pachón, Ángeles Vaz, Sara Salvador-Martín, María Sanjurjo-Sáez, Luis A López-Fernández. New DPYD variants causing DPD deficiency in patients treated with fluoropyrimidine. Cancer chemotherapy and pharmacology. 2020 07; 86(1):45-54. doi: 10.1007/s00280-020-04093-1. [PMID: 32529295]
  • Tiphaine Robin, Franck Saint-Marcoux, Doriane Toinon, Naïma Tafzi, Pierre Marquet, Souleiman El Balkhi. Automatic quantification of uracil and dihydrouracil in plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Apr; 1142(?):122038. doi: 10.1016/j.jchromb.2020.122038. [PMID: 32169798]
  • Jihane Basbous, Antoine Aze, Laurent Chaloin, Rana Lebdy, Dana Hodroj, Cyril Ribeyre, Marion Larroque, Caitlin Shepard, Baek Kim, Alain Pruvost, Jérôme Moreaux, Domenico Maiorano, Marcel Mechali, Angelos Constantinou. Dihydropyrimidinase protects from DNA replication stress caused by cytotoxic metabolites. Nucleic acids research. 2020 02; 48(4):1886-1904. doi: 10.1093/nar/gkz1162. [PMID: 31853544]
  • Shinji Kobuchi, Mako Akutagawa, Yukako Ito, Toshiyuki Sakaeda. Association between the pharmacokinetics of capecitabine and the plasma dihydrouracil to uracil ratio in rat: A surrogate biomarker for dihydropyrimidine dehydrogenase activity. Biopharmaceutics & drug disposition. 2019 Jan; 40(1):44-48. doi: 10.1002/bdd.2168. [PMID: 30592773]
  • Linda M Henricks, Bart A W Jacobs, Didier Meulendijks, Dick Pluim, Daan van den Broek, Niels de Vries, Hilde Rosing, Jos H Beijnen, Alwin D R Huitema, Henk-Jan Guchelaar, Annemieke Cats, Jan H M Schellens. Food-effect study on uracil and dihydrouracil plasma levels as marker for dihydropyrimidine dehydrogenase activity in human volunteers. British journal of clinical pharmacology. 2018 12; 84(12):2761-2769. doi: 10.1111/bcp.13719. [PMID: 30047584]
  • Olavo Vicente Neto, Suziane Raymundo, Maria Alice Franzoi, Andiara do Carmo Artmann, Mariane Tegner, Victoria Vendramini Müller, Roberta Zilles Hahn, Gustavo Vasconcelos Alves, Gilberto Schwartsmann, Rafael Linden, Marina Venzon Antunes. DPD functional tests in plasma, fresh saliva and dried saliva samples as predictors of 5-fluorouracil exposure and occurrence of drug-related severe toxicity. Clinical biochemistry. 2018 Jun; 56(?):18-25. doi: 10.1016/j.clinbiochem.2018.04.001. [PMID: 29625079]
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  • Yoko Nakajima, Judith Meijer, Doreen Dobritzsch, Tetsuya Ito, Chunhua Zhang, Xu Wang, Yoriko Watanabe, Kyoko Tashiro, Rutger Meinsma, Jeroen Roelofsen, Lida Zoetekouw, André B P van Kuilenburg. Dihydropyrimidinase deficiency in four East Asian patients due to novel and rare DPYS mutations affecting protein structural integrity and catalytic activity. Molecular genetics and metabolism. 2017 12; 122(4):216-222. doi: 10.1016/j.ymgme.2017.10.003. [PMID: 29054612]
  • Wen Pan, Yuandong Li, Yan Feng, Fan Yang, Haizhou Liu. A new sample preparation and separation combination for the precise, accurate, and simultaneous determination of uracil and dihydrouracil in human plasma by reversed-phase HPLC. Journal of separation science. 2017 Oct; 40(19):3763-3770. doi: 10.1002/jssc.201700279. [PMID: 28726286]
  • Didier Meulendijks, Linda M Henricks, Bart A W Jacobs, Abidin Aliev, Maarten J Deenen, Niels de Vries, Hilde Rosing, Erik van Werkhoven, Anthonius de Boer, Jos H Beijnen, Caroline M P W Mandigers, Marcel Soesan, Annemieke Cats, Jan H M Schellens. Pretreatment serum uracil concentration as a predictor of severe and fatal fluoropyrimidine-associated toxicity. British journal of cancer. 2017 May; 116(11):1415-1424. doi: 10.1038/bjc.2017.94. [PMID: 28427087]
  • Andrés Fernando Andrade Galarza, Rafael Linden, Marina Venzon Antunes, Roberta Zilles Hahn, Suziane Raymundo, Anne Caroline Cezimbra da Silva, Rodrigo Staggemeier, Fernando Rosado Spilki, Gilberto Schwartsmann. Endogenous plasma and salivary uracil to dihydrouracil ratios and DPYD genotyping as predictors of severe fluoropyrimidine toxicity in patients with gastrointestinal malignancies. Clinical biochemistry. 2016 Nov; 49(16-17):1221-1226. doi: 10.1016/j.clinbiochem.2016.07.004. [PMID: 27399164]
  • Bart A W Jacobs, Maarten J Deenen, Dick Pluim, J G Coen van Hasselt, Martin D Krähenbühl, Robin M J M van Geel, Niels de Vries, Hilde Rosing, Didier Meulendijks, Artur M Burylo, Annemieke Cats, Jos H Beijnen, Alwin D R Huitema, Jan H M Schellens. Pronounced between-subject and circadian variability in thymidylate synthase and dihydropyrimidine dehydrogenase enzyme activity in human volunteers. British journal of clinical pharmacology. 2016 09; 82(3):706-16. doi: 10.1111/bcp.13007. [PMID: 27161955]
  • Bart A W Jacobs, Hilde Rosing, Niels de Vries, Didier Meulendijks, Linda M Henricks, Jan H M Schellens, Jos H Beijnen. Development and validation of a rapid and sensitive UPLC-MS/MS method for determination of uracil and dihydrouracil in human plasma. Journal of pharmaceutical and biomedical analysis. 2016 Jul; 126(?):75-82. doi: 10.1016/j.jpba.2016.04.039. [PMID: 27179185]
  • Maurice C van Staveren, Andre B P van Kuilenburg, Henk-Jan Guchelaar, Judith Meijer, Cornelis J A Punt, Robert S de Jong, Hans Gelderblom, Jan Gerard Maring. Evaluation of an oral uracil loading test to identify DPD-deficient patients using a limited sampling strategy. British journal of clinical pharmacology. 2016 Mar; 81(3):553-61. doi: 10.1111/bcp.12821. [PMID: 26551538]
  • F Thomas, I Hennebelle, C Delmas, I Lochon, C Dhelens, C Garnier Tixidre, A Bonadona, N Penel, A Goncalves, J P Delord, C Toulas, E Chatelut. Genotyping of a family with a novel deleterious DPYD mutation supports the pretherapeutic screening of DPD deficiency with dihydrouracil/uracil ratio. Clinical pharmacology and therapeutics. 2016 Feb; 99(2):235-42. doi: 10.1002/cpt.210. [PMID: 26265035]
  • Roberta Zilles Hahn, Andrés Fernando Andrade Galarza, Anelise Schneider, Marina Venzon Antunes, Gilberto Schwartsmann, Rafael Linden. Improved determination of uracil and dihydrouracil in plasma after a loading oral dose of uracil using high-performance liquid chromatography with photodiode array detection and porous graphitic carbon stationary phase. Clinical biochemistry. 2015 Sep; 48(13-14):915-8. doi: 10.1016/j.clinbiochem.2015.04.019. [PMID: 25940841]
  • Drupad K Trivedi, Ray K Iles. Shotgun metabolomic profiles in maternal urine identify potential mass spectral markers of abnormal fetal biochemistry - dihydrouracil and progesterone in the metabolism of Down syndrome. Biomedical chromatography : BMC. 2015 Aug; 29(8):1173-83. doi: 10.1002/bmc.3404. [PMID: 25545476]
  • Maurice C van Staveren, Frans Opdam, Henk-Jan Guchelaar, André B P van Kuilenburg, Jan Gerard Maring, Hans Gelderblom. Influence of metastatic disease on the usefulness of uracil pharmacokinetics as a screening tool for DPD activity in colorectal cancer patients. Cancer chemotherapy and pharmacology. 2015 Jul; 76(1):47-52. doi: 10.1007/s00280-015-2746-3. [PMID: 25957957]
  • Johanna Sistonen, Barbara Büchel, Tanja K Froehlich, Dominic Kummer, Stefano Fontana, Markus Joerger, André B P van Kuilenburg, Carlo R Largiadèr. Predicting 5-fluorouracil toxicity: DPD genotype and 5,6-dihydrouracil:uracil ratio. Pharmacogenomics. 2014 Sep; 15(13):1653-66. doi: 10.2217/pgs.14.126. [PMID: 25410891]
  • C F Saba, C W Schmiedt, K G Freeman, G L Edwards. Indirect assessment of dihydropyrimidine dehydrogenase activity in cats. Veterinary and comparative oncology. 2013 Dec; 11(4):265-71. doi: 10.1111/vco.12064. [PMID: 24007333]
  • Shinji Kobuchi, Shota Kuwano, Kazuki Imoto, Kae Okada, Asako Nishimura, Yukako Ito, Nobuhito Shibata, Kanji Takada. A predictive biomarker for altered 5-fluorouracil pharmacokinetics following repeated administration in a rat model of colorectal cancer. Biopharmaceutics & drug disposition. 2013 Oct; 34(7):365-76. doi: 10.1002/bdd.1851. [PMID: 23836081]
  • C W Yeung, M M Yau, C K Ma, T S Siu, Sidney Tam, C W Lam. Diagnosis of dihydropyrimidinase deficiency in a Chinese boy with dihydropyrimidinuria. Hong Kong medical journal = Xianggang yi xue za zhi. 2013 Jun; 19(3):272-5. doi: 10.12809/hkmj133598. [PMID: 23732435]
  • Shinji Kobuchi, Yukako Ito, Kae Okada, Kazuki Imoto, Shota Kuwano, Kanji Takada. Pharmacokinetic/pharmacodynamic modeling of 5-fluorouracil by using a biomarker to predict tumor growth in a rat model of colorectal cancer. Journal of pharmaceutical sciences. 2013 Jun; 102(6):2056-2067. doi: 10.1002/jps.23547. [PMID: 23592368]
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  • François Coudoré, Denis Roche, Sandrine Lefeuvre, Delphine Faussot, Eliane M Billaud, Marie-Anne Loriot, Philippe Beaune. Validation of an ultra-high performance liquid chromatography tandem mass spectrometric method for quantifying uracil and 5,6-dihydrouracil in human plasma. Journal of chromatographic science. 2012 Nov; 50(10):877-84. doi: 10.1093/chromsci/bms085. [PMID: 22689904]
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  • Yvonne Wettergren, Göran Carlsson, Elisabeth Odin, Bengt Gustavsson. Pretherapeutic uracil and dihydrouracil levels of colorectal cancer patients are associated with sex and toxic side effects during adjuvant 5-fluorouracil-based chemotherapy. Cancer. 2012 Jun; 118(11):2935-43. doi: 10.1002/cncr.26595. [PMID: 22020693]
  • André B P van Kuilenburg, Peter Häusler, Andreas Schalhorn, Michael W T Tanck, Johannes H Proost, Christoph Terborg, Detlev Behnke, Wolfgang Schwabe, Kati Jabschinsky, Jan Gerard Maring. Evaluation of 5-fluorouracil pharmacokinetics in cancer patients with a c.1905+1G>A mutation in DPYD by means of a Bayesian limited sampling strategy. Clinical pharmacokinetics. 2012 Mar; 51(3):163-74. doi: 10.1007/bf03257473. [PMID: 22339448]
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