Orotic acid (BioDeep_00000400255)

Main id: BioDeep_00000001401

Secondary id: BioDeep_00000400026

natural product PANOMIX_OTCML-2023 BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


Orotic acid ,Anhydrous

化学式: C5H4N2O4 (156.0171064)
中文名称: 乙氧代妥尔油脂肪酸, 乳清酸, 乳清酸 一水合物
谱图信息: 最多检出来源 Homo sapiens(blood) 1.26%

分子结构信息

SMILES: C1=C(NC(=O)NC1=O)C(=O)O
InChI: InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)

描述信息

A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.
Orotic acid (6-Carboxyuracil), a precursor in biosynthesis of pyrimidine nucleotides and RNA, is released from the mitochondrial dihydroorotate dehydrogenase (DHODH) for conversion to UMP by the cytoplasmic UMP synthase enzyme. Orotic acid is a marker for measurement in routine newborn screening for urea cycle disorders. Orotic acid can induce hepatic steatosis and hepatomegaly in rats[1][2][3].

同义名列表

7 个代谢物同义名

POE (12) TALL OIL; Orotic acid; Orotic acid ,Anhydrous; 6-Carboxyuracil; Vitamin B13; Orotate; Orotic acid



数据库引用编号

79 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(1)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

13 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

  • Lukas Babylon, Julia Meißner, Gunter P Eckert. Combination of Secondary Plant Metabolites and Micronutrients Improves Mitochondrial Function in a Cell Model of Early Alzheimer's Disease. International journal of molecular sciences. 2023 Jun; 24(12):. doi: 10.3390/ijms241210029. [PMID: 37373177]
  • Fabrice A Müller, Marianna Stamou, Felix H Englert, Ole Frenzel, Sabine Diedrich, Laura Suter-Dick, John F Wambaugh, Shana J Sturla. In vitro to in vivo extrapolation and high-content imaging for simultaneous characterization of chemically induced liver steatosis and markers of hepatotoxicity. Archives of toxicology. 2023 Apr; ?(?):. doi: 10.1007/s00204-023-03490-8. [PMID: 37046073]
  • Xiaoyue Li, Beibei Zeng, Lu Wen, Yingcai Zhao, Zhaojie Li, Changhu Xue, Tiantian Zhang, Yuming Wang. Sea Cucumber Saponins Derivatives Alleviate Hepatic Lipid Accumulation Effectively in Fatty Acids-Induced HepG2 Cells and Orotic Acid-Induced Rats. Marine drugs. 2022 Nov; 20(11):. doi: 10.3390/md20110703. [PMID: 36355027]
  • Austin Clyde, Stephanie Galanie, Daniel W Kneller, Heng Ma, Yadu Babuji, Ben Blaiszik, Alexander Brace, Thomas Brettin, Kyle Chard, Ryan Chard, Leighton Coates, Ian Foster, Darin Hauner, Vilmos Kertesz, Neeraj Kumar, Hyungro Lee, Zhuozhao Li, Andre Merzky, Jurgen G Schmidt, Li Tan, Mikhail Titov, Anda Trifan, Matteo Turilli, Hubertus Van Dam, Srinivas C Chennubhotla, Shantenu Jha, Andrey Kovalevsky, Arvind Ramanathan, Martha S Head, Rick Stevens. High-Throughput Virtual Screening and Validation of a SARS-CoV-2 Main Protease Noncovalent Inhibitor. Journal of chemical information and modeling. 2022 01; 62(1):116-128. doi: 10.1021/acs.jcim.1c00851. [PMID: 34793155]
  • Daniel W Kneller, Hui Li, Stephanie Galanie, Gwyndalyn Phillips, Audrey Labbé, Kevin L Weiss, Qiu Zhang, Mark A Arnould, Austin Clyde, Heng Ma, Arvind Ramanathan, Colleen B Jonsson, Martha S Head, Leighton Coates, John M Louis, Peter V Bonnesen, Andrey Kovalevsky. Structural, Electronic, and Electrostatic Determinants for Inhibitor Binding to Subsites S1 and S2 in SARS-CoV-2 Main Protease. Journal of medicinal chemistry. 2021 12; 64(23):17366-17383. doi: 10.1021/acs.jmedchem.1c01475. [PMID: 34705466]
  • 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]
  • Mihaela Zabulica, Raghuraman C Srinivasan, Pinar Akcakaya, Gabriella Allegri, Burcu Bestas, Mike Firth, Christina Hammarstedt, Tomas Jakobsson, Towe Jakobsson, Ewa Ellis, Carl Jorns, Georgios Makris, Tanja Scherer, Nicole Rimann, Natalie R van Zuydam, Roberto Gramignoli, Anna Forslöw, Susanna Engberg, Marcello Maresca, Olav Rooyackers, Beat Thöny, Johannes Häberle, Barry Rosen, Stephen C Strom. Correction of a urea cycle defect after ex vivo gene editing of human hepatocytes. Molecular therapy : the journal of the American Society of Gene Therapy. 2021 05; 29(5):1903-1917. doi: 10.1016/j.ymthe.2021.01.024. [PMID: 33484963]
  • Go Sugahara, Chihiro Yamasaki, Ami Yanagi, Suzue Furukawa, Yuko Ogawa, Akinari Fukuda, Shin Enosawa, Akihiro Umezawa, Yuji Ishida, Chise Tateno. Humanized liver mouse model with transplanted human hepatocytes from patients with ornithine transcarbamylase deficiency. Journal of inherited metabolic disease. 2021 05; 44(3):618-628. doi: 10.1002/jimd.12347. [PMID: 33336822]
  • Hitesh Verma, Rajeev Garg. Development, optimization and characterization of chewable tablet containing synergistic combination of magnesium orotate dihydrate with cholecalciferol and menaquinone-7 for management of hyperglycemia and its pharmacokinetic study. Magnesium research. 2021 05; 34(2):43-63. doi: 10.1684/mrh.2021.0487. [PMID: 34463282]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Brian J Koos, Jeffrey A Gornbein. Early pregnancy metabolites predict gestational diabetes mellitus: implications for fetal programming. American journal of obstetrics and gynecology. 2021 02; 224(2):215.e1-215.e7. doi: 10.1016/j.ajog.2020.07.050. [PMID: 32739399]
  • Chie Yokouchi, Yukari Nishimura, Hirohiko Goto, Makoto Sato, Yuya Hidoh, Kenji Takeuchi, Yuji Ishii. Reduction of fatty liver in rats by nicotinamide via the regeneration of the methionine cycle and the inhibition of aldehyde oxidase. The Journal of toxicological sciences. 2021; 46(1):31-42. doi: 10.2131/jts.46.31. [PMID: 33408299]
  • Usman A Tahir, Daniel H Katz, Tianyi Zhao, Debby Ngo, Daniel E Cruz, Jeremy M Robbins, Zsu-Zsu Chen, Bennet Peterson, Mark D Benson, Xu Shi, Lucas Dailey, Charlotte Andersson, Ramachandran S Vasan, Yan Gao, Changyu Shen, Adolfo Correa, Michael E Hall, Thomas J Wang, Clary B Clish, James G Wilson, Robert E Gerszten. Metabolomic Profiles and Heart Failure Risk in Black Adults: Insights From the Jackson Heart Study. Circulation. Heart failure. 2021 01; 14(1):e007275. doi: 10.1161/circheartfailure.120.007275. [PMID: 33464957]
  • Lozan Todorov, Maria Traykova, Luciano Saso, Irena Kostova. In Vitro Interaction of 5-Aminoorotic Acid and Its Gallium(III) Complex with Superoxide Radical, Generated by Two Model Systems. International journal of molecular sciences. 2020 Nov; 21(22):. doi: 10.3390/ijms21228862. [PMID: 33238535]
  • Yucheng Hu, Jingqi Xu, Qian Chen, Mengyang Liu, Sijian Wang, Haiyang Yu, Yi Zhang, Tao Wang. Regulation effects of total flavonoids in Morus alba L. on hepatic cholesterol disorders in orotic acid induced NAFLD rats. BMC complementary medicine and therapies. 2020 Aug; 20(1):257. doi: 10.1186/s12906-020-03052-w. [PMID: 32807146]
  • Johanna Matilainen, Anne-Mari Mustonen, Kirsi Rilla, Reijo Käkelä, Sanna P Sihvo, Petteri Nieminen. Orotic acid-treated hepatocellular carcinoma cells resist steatosis by modification of fatty acid metabolism. Lipids in health and disease. 2020 Apr; 19(1):70. doi: 10.1186/s12944-020-01243-5. [PMID: 32284043]
  • Dionysius Subali, Mi Hye Kwon, Won Seok Bang, Hee Eun Kang. The pharmacokinetics of mycophenolic acid in rats with orotic acid induced nonalcoholic fatty liver disease. Canadian journal of physiology and pharmacology. 2020 Mar; 98(3):169-176. doi: 10.1139/cjpp-2019-0383. [PMID: 31652406]
  • Si-Jian Wang, Qian Chen, Meng-Yang Liu, Hai-Yang Yu, Jing-Qi Xu, Jia-Qi Wu, Yi Zhang, Tao Wang. Regulation effects of rosemary (Rosmarinus officinalis Linn.) on hepatic lipid metabolism in OA induced NAFLD rats. Food & function. 2019 Nov; 10(11):7356-7365. doi: 10.1039/c9fo01677e. [PMID: 31650134]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Gillian O Bruni, Keili Zhong, Soo Chan Lee, Ping Wang. CRISPR-Cas9 induces point mutation in the mucormycosis fungus Rhizopus delemar. Fungal genetics and biology : FG & B. 2019 03; 124(?):1-7. doi: 10.1016/j.fgb.2018.12.002. [PMID: 30562583]
  • Naoyoshi Kumakura, Akiko Ueno, Ken Shirasu. Establishment of a selection marker recycling system for sequential transformation of the plant-pathogenic fungus Colletotrichum orbiculare. Molecular plant pathology. 2019 03; 20(3):447-459. doi: 10.1111/mpp.12766. [PMID: 30390402]
  • Abdelkader Hassani, Siti Aslina Hussain, Norhafizah Abdullah, Suryani Kamarudin, Rozita Rosli. Antioxidant Potential and Angiotensin-Converting Enzyme (ACE) Inhibitory Activity of Orotic Acid-Loaded Gum Arabic Nanoparticles. AAPS PharmSciTech. 2019 Jan; 20(2):53. doi: 10.1208/s12249-018-1238-2. [PMID: 30617521]
  • Won Seok Bang, Ye Ran Hwang, Zhengri Li, Inchul Lee, Hee Eun Kang. Effects of Orotic Acid-Induced Non-Alcoholic Fatty Liver on the Pharmacokinetics of Metoprolol and its Metabolites in Rats. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2019; 22(1):98-111. doi: 10.18433/jpps30268. [PMID: 30786957]
  • Orhan Destanoğlu, Damla Zeydanlı, Mehmet Şerif Cansever, Gülçin Gümüş Yılmaz. Ion chromatographic method for the determination of orotic acid in urine. Analytical biochemistry. 2018 12; 563(?):9-14. doi: 10.1016/j.ab.2018.09.016. [PMID: 30267708]
  • Yong Tan, Cheng Lu, Miao Jiang, Ning Zhao, Li Li, Shanshan Shen, Fulan Guan, Bing He, Cheng Xiao, Aiping L, Shiping Cheng, Xianpeng Zu, Weidong Zhang, Xinru Liu. Exploring pathogenesis in subjects with subjective Tinnitus having kidney deficiency pattern in terms of Traditional Chinese Medicine based on serum metabolic profiles. Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan. 2018 10; 38(5):773-780. doi: . [PMID: 32185996]
  • Mengru Chang, Tiantian Zhang, Xiuqing Han, Qingjuan Tang, Teruyoshi Yanagita, Jie Xu, Changhu Xue, Yuming Wang. Comparative Analysis of EPA/DHA-PL Forage and Liposomes in Orotic Acid-Induced Nonalcoholic Fatty Liver Rats and Their Related Mechanisms. Journal of agricultural and food chemistry. 2018 Feb; 66(6):1408-1418. doi: 10.1021/acs.jafc.7b05173. [PMID: 29345914]
  • Saskia B Wortmann, Margaret A Chen, Roberto Colombo, Alessandro Pontoglio, Bader Alhaddad, Lorenzo D Botto, Tatiana Yuzyuk, Curtis R Coughlin, Maria Descartes, Stephanie Grűnewald, Bruno Maranda, Philippa B Mills, James Pitt, Catherine Potente, Richard Rodenburg, Leo A J Kluijtmans, Srirangan Sampath, Emil F Pai, Ron A Wevers, George E Tiller. Mild orotic aciduria in UMPS heterozygotes: a metabolic finding without clinical consequences. Journal of inherited metabolic disease. 2017 05; 40(3):423-431. doi: 10.1007/s10545-017-0015-9. [PMID: 28205048]
  • Yanjun Liu, Di Shi, Yingying Tian, Yuntao Liu, Qiping Zhan, Jie Xu, Jingfeng Wang, Changhu Xue. Eicosapentaenoic Acid-Enriched Phosphatidylcholine Attenuated Hepatic Steatosis Through Regulation of Cholesterol Metabolism in Rats with Nonalcoholic Fatty Liver Disease. Lipids. 2017 02; 52(2):119-127. doi: 10.1007/s11745-016-4222-1. [PMID: 28012135]
  • Yu Kyong Kim, Mun Ju Choi, Tae Young Oh, Kyung-Sang Yu, SeungHwan Lee. A comparative pharmacokinetic and tolerability analysis of the novel orotic acid salt form of tenofovir disoproxil and the fumaric acid salt form in healthy subjects. Drug design, development and therapy. 2017; 11(?):3171-3177. doi: 10.2147/dddt.s149125. [PMID: 29158663]
  • William L Nyhan, Jon A Gangoiti. Hereditary Orotic Aciduria and the Excretion of Orotidine. Neuropediatrics. 2016 Dec; 47(6):408-409. doi: 10.1055/s-0036-1587594. [PMID: 27574833]
  • M Löffler, E A Carrey, E Zameitat. Orotate (orotic acid): An essential and versatile molecule. Nucleosides, nucleotides & nucleic acids. 2016 Dec; 35(10-12):566-577. doi: 10.1080/15257770.2016.1147580. [PMID: 27906623]
  • John A Duley, Michael G Henman, Kevin H Carpenter, Michael J Bamshad, George A Marshall, Chee Y Ooi, Bridget Wilcken, Jason R Pinner. Elevated plasma dihydroorotate in Miller syndrome: Biochemical, diagnostic and clinical implications, and treatment with uridine. Molecular genetics and metabolism. 2016 09; 119(1-2):83-90. doi: 10.1016/j.ymgme.2016.06.008. [PMID: 27370710]
  • Takehito Nakazawa, Masami Tsuzuki, Toshikazu Irie, Masahiro Sakamoto, Yoichi Honda. Marker recycling via 5-fluoroorotic acid and 5-fluorocytosine counter-selection in the white-rot agaricomycete Pleurotus ostreatus. Fungal biology. 2016 09; 120(9):1146-55. doi: 10.1016/j.funbio.2016.06.011. [PMID: 27567720]
  • NULL. In brief: Uridine triacetate (Xuriden) for hereditary orotic aciduria. The Medical letter on drugs and therapeutics. 2016 Mar; 58(1491):e49. doi: NULL. [PMID: 27027693]
  • Xiuqing Han, Chunhua Liu, Yong Xue, Jingfeng Wang, Changhu Xue, Teruyoshi Yanagita, Xiang Gao, Yuming Wang. Long-term fatty liver-induced insulin resistance in orotic acid-induced nonalcoholic fatty liver rats. Bioscience, biotechnology, and biochemistry. 2016; 80(4):735-43. doi: 10.1080/09168451.2015.1123608. [PMID: 26775542]
  • Asher Mullard. FDA approves ultra-orphan drug on a 4-patient trial. Nature reviews. Drug discovery. 2015 Oct; 14(10):669. doi: 10.1038/nrd4756. [PMID: 26424352]
  • Sheng Yin, Shpend Dragusha, Valon Ejupi, Takayuki Shibata, Tsutomu Kabashima, Masaaki Kai. Sensitive and Selective Determination of Orotic Acid in Biological Specimens Using a Novel Fluorogenic Reaction. Journal of fluorescence. 2015 Jul; 25(4):1005-11. doi: 10.1007/s10895-015-1584-3. [PMID: 26026930]
  • Wenjia Tong, Danqun Jin, Jingmin Sun. [Report of a case with late-onset ornithine transcarbamylase deficiency with gas chromatography-mass spectrometry and DNA sequencing confirmation and literatures review]. Zhonghua er ke za zhi = Chinese journal of pediatrics. 2015 May; 53(5):366-9. doi: NULL. [PMID: 26080667]
  • You-Jin Choi, Yujin Yoon, Kang-Yo Lee, Yun-Pyo Kang, Dong Kyu Lim, Sung Won Kwon, Keon-Wook Kang, Seung-Mi Lee, Byung-Hoon Lee. Orotic acid induces hypertension associated with impaired endothelial nitric oxide synthesis. Toxicological sciences : an official journal of the Society of Toxicology. 2015 Apr; 144(2):307-17. doi: 10.1093/toxsci/kfv003. [PMID: 25601987]
  • Kenji Takeuchi, Hirohiko Goto, Yuko Ito, Makoto Sato, Satoshi Matsumoto, Tadashi Senba, Hideyuki Yamada, Ken Umehara. Dehydroepiandrosterone sulfate and cytochrome P450 inducers alleviate fatty liver in male rats fed an orotic acid-supplemented diet. The Journal of toxicological sciences. 2015 Apr; 40(2):181-91. doi: 10.2131/jts.40.181. [PMID: 25786523]
  • Tatyana N Tarasenko, Odrick R Rosas, Larry N Singh, Kara Kristaponis, Hilary Vernon, Peter J McGuire. A new mouse model of mild ornithine transcarbamylase deficiency (spf-j) displays cerebral amino acid perturbations at baseline and upon systemic immune activation. PloS one. 2015; 10(2):e0116594. doi: 10.1371/journal.pone.0116594. [PMID: 25647322]
  • Katsumi Shibata, Nobuya Morita, Tomoyo Kawamura, Ai Tsuji, Tsutomu Fukuwatari. Effects of Fatty Liver Induced by Excess Orotic Acid on B-Group Vitamin Concentrations of Liver, Blood, and Urine in Rats. Journal of nutritional science and vitaminology. 2015; 61(5):355-61. doi: 10.3177/jnsv.61.355. [PMID: 26639842]
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  • Eun-Jeong Jung, Kang-Yo Lee, Byung-Hoon Lee. Proliferating effect of orotic acid through mTORC1 activation mediated by negative regulation of AMPK in SK-Hep1 hepatocellular carcinoma cells. The Journal of toxicological sciences. 2012; 37(4):813-21. doi: 10.2131/jts.37.813. [PMID: 22863860]
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