Orotidine (BioDeep_00000017895)

 

Secondary id: BioDeep_00000405365

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

化学式: C10H12N2O8 (288.0593632)
中文名称: 乳清苷, 乳清酸核苷
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.78%

Reviewed

Last reviewed on 2024-07-16.

Cite this Page

Orotidine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/orotidine (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000017895). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=C(N(C(=O)NC1=O)C2C(C(C(O2)CO)O)O)C(=O)O
InChI: InChI=1S/C10H12N2O8/c13-2-4-6(15)7(16)8(20-4)12-3(9(17)18)1-5(14)11-10(12)19/h1,4,6-8,13,15-16H,2H2,(H,17,18)(H,11,14,19)/t4-,6-,7-,8-/m1/s1

描述信息

Orotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a beta-N1-glycosidic bond. It is a water-soluble solid. Orotidine is found in bacteria, fungi, plants, and animals. In humans, orotidine occurs as its 5-phosphate (orotidylic acid), which is an intermediate in the biosynthesis of pyrimidine nucleosides (cytidine and uridine) that are found in nucleic acids (as the nucleotides containing the bases cytosine and uracil). Orotidine itself is not a component of nucleic acid. Orotidine monophosphate (OMP) is converted to uridine monophosphate by OMP decarboxylase, which is inhibited by mononucleotide precursors. Large amounts of orotidine are excreted in the urine of cancer patients treated with 6-azauridine, which is one such inhibitor, indicating that the subject has increased DNA synthesis due to cancer. Orotidine was first isolated from a mutant strain of the fungus Neurospora by A. Michael Michelson, William Drell, and Herschel K. Mitchell (PMID: 14853953).
Isolated from Phaseolus vulgaris (kidney bean)

Orotidine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=314-50-1 (retrieved 2024-07-16) (CAS RN: 314-50-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

8 个代谢物同义名

3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid; 3-Ribofuranosylorotic acid; Orotidine, ammonium salt; 3-Ribofuranosylorotate; Orotic acid riboside; 6-Carboxyuridine; SCHEMBL20895; Orotidine



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

8 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

  • Péter Monostori, Glynis Klinke, Jana Hauke, Sylvia Richter, Jörgen Bierau, Sven F Garbade, Georg F Hoffmann, Claus-Dieter Langhans, Dorothea Haas, Jürgen G Okun. Extended diagnosis of purine and pyrimidine disorders from urine: LC MS/MS assay development and clinical validation. PloS one. 2019; 14(2):e0212458. doi: 10.1371/journal.pone.0212458. [PMID: 30817767]
  • 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]
  • Dae Eun Choi, Kang Wook Lee, Young Tai Shin, Ki Ryang Na. Hyperammonemia in a patient with late-onset ornithine carbamoyltransferase deficiency. Journal of Korean medical science. 2012 May; 27(5):556-9. doi: 10.3346/jkms.2012.27.5.556. [PMID: 22563224]
  • Naimeh Taheri-Talesh, Yi Xiong, Berl R Oakley. The functions of myosin II and myosin V homologs in tip growth and septation in Aspergillus nidulans. PloS one. 2012; 7(2):e31218. doi: 10.1371/journal.pone.0031218. [PMID: 22359575]
  • Leena Pohjala, Age Utt, Margus Varjak, Aleksei Lulla, Andres Merits, Tero Ahola, Päivi Tammela. Inhibitors of alphavirus entry and replication identified with a stable Chikungunya replicon cell line and virus-based assays. PloS one. 2011; 6(12):e28923. doi: 10.1371/journal.pone.0028923. [PMID: 22205980]
  • C J Bailey. Orotic aciduria and uridine monophosphate synthase: a reappraisal. Journal of inherited metabolic disease. 2009 Dec; 32 Suppl 1(?):S227-33. doi: 10.1007/s10545-009-1176-y. [PMID: 19562503]
  • Michael J Lewis, Hugh R B Pelham. Inefficient quality control of thermosensitive proteins on the plasma membrane. PloS one. 2009; 4(4):e5038. doi: 10.1371/journal.pone.0005038. [PMID: 19337370]
  • Konrad Oexle. Biochemical data in ornithine transcarbamylase deficiency (OTCD) carrier risk estimation: logistic discrimination and combination with genetic information. Journal of human genetics. 2006; 51(3):204-208. doi: 10.1007/s10038-005-0345-6. [PMID: 16453063]
  • André B P van Kuilenburg, Henk van Lenthe, Monika Löffler, Albert H van Gennip. Analysis of pyrimidine synthesis "de novo" intermediates in urine and dried urine filter- paper strips with HPLC-electrospray tandem mass spectrometry. Clinical chemistry. 2004 Nov; 50(11):2117-24. doi: 10.1373/clinchem.2004.038869. [PMID: 15375016]
  • Ana M Pita, Angeles Fernandez-Bustos, Margarita Rodes, Jose A Arranz, Cesar Fisac, Nuria Virgili, Joan Soler, Yasuo Wakabayashi. Orotic aciduria and plasma urea cycle-related amino acid alterations in short bowel syndrome, evoked by an arginine-free diet. JPEN. Journal of parenteral and enteral nutrition. 2004 Sep; 28(5):315-23. doi: 10.1177/0148607104028005315. [PMID: 15449570]
  • S Grünewald, L Fairbanks, S Genet, T Cranston, J Hüsing, J V Leonard, M P Champion. How reliable is the allopurinol load in detecting carriers for ornithine transcarbamylase deficiency?. Journal of inherited metabolic disease. 2004; 27(2):179-86. doi: 10.1023/b:boli.0000028727.77454.bd. [PMID: 15159648]
  • Riko Katahira, Hiroshi Ashihara. Profiles of pyrimidine biosynthesis, salvage and degradation in disks of potato (Solanum tuberosum L.) tubers. Planta. 2002 Sep; 215(5):821-8. doi: 10.1007/s00425-002-0806-5. [PMID: 12244448]
  • David Friedecký, Tomás Adam, Petr Barták. Capillary electrophoresis for detection of inherited disorders of purine and pyrimidine metabolism: a selective approach. Electrophoresis. 2002 Feb; 23(4):565-71. doi: 10.1002/1522-2683(200202)23:4<565::aid-elps565>3.0.co;2-s. [PMID: 11870766]
  • H Nagasaka, T Yorifuji, H Egawa, H Kikuta, K Tanaka, K Kobayashi. Successful living-donor liver transplantation from an asymptomatic carrier mother in ornithine transcarbamylase deficiency. The Journal of pediatrics. 2001 Mar; 138(3):432-4. doi: 10.1067/mpd.2001.111318. [PMID: 11241058]
  • E Riudor, J A Arranz, M Rodés, V Rubio, M Sentís, A B Burlina. Influence of dose and age on the response of the allopurinol test for ornithine carbamoyltransferase deficiency in control infants. Journal of inherited metabolic disease. 2000 Nov; 23(7):662-8. doi: 10.1023/a:1005610325170. [PMID: 11117427]
  • J A Arranz, E Riudor, M Rodés, M Roig, C Climent, V Rubio, M Sentís, A Burlina. Optimization of allopurinol challenge: sample purification, protein intake control, and the use of orotidine response as a discriminative variable improve performance of the test for diagnosing ornithine carbamoyltransferase deficiency. Clinical chemistry. 1999 Jul; 45(7):995-1001. doi: 10.1093/clinchem/45.7.995. [PMID: 10388475]
  • J R Bonham, P Guthrie, M Downing, J C Allen, M S Tanner, M Sharrard, C Rittey, J M Land, A Fensom, D O'Neill, J A Duley, L D Fairbanks. The allopurinol load test lacks specificity for primary urea cycle defects but may indicate unrecognized mitochondrial disease. Journal of inherited metabolic disease. 1999 Apr; 22(2):174-84. doi: 10.1023/a:1005406205548. [PMID: 10234613]
  • A E Lund. Quick cancer test developed. Journal of the American Dental Association (1939). 1998 Aug; 129(8):1080, 1082. doi: 10.14219/jada.archive.1998.0371. [PMID: 9715008]
  • M A Carducci, M Choti, N E Maestri, S W Brusilow. Allopurinol-induced pyrimidinuria in cancer patients. In vivo (Athens, Greece). 1998 May; 12(3):271-4. doi: NULL. [PMID: 9706470]
  • T Yamamoto, Y Moriwaki, S Takahashi, Z Tsutsumi, J Yamakita, K Higashino. Effect of allopurinol and benzbromarone on the concentration of uridine in plasma. Metabolism: clinical and experimental. 1997 Dec; 46(12):1473-6. doi: 10.1016/s0026-0495(97)90151-7. [PMID: 9439546]
  • N Kobayashi, F Hariguchi, T Okamoto, Y Okada, T Hayashi, T Matsuno. Antagonistic effect of nucleic acid precursors on the anticoccidial activity of 6-azauracil. The Journal of veterinary medical science. 1996 Feb; 58(2):121-7. doi: 10.1292/jvms.58.121. [PMID: 8672581]
  • I Sebesta, L D Fairbanks, P M Davies, H A Simmonds, J V Leonard. The allopurinol loading test for identification of carriers for ornithine carbamoyl transferase deficiency: studies in a healthy control population and females at risk. Clinica chimica acta; international journal of clinical chemistry. 1994 Jan; 224(1):45-54. doi: 10.1016/0009-8981(94)90119-8. [PMID: 8174277]
  • I Sebesta, J Krijt, L D Fairbanks, H A Simmonds. The allopurinol loading test in detecting obligate heterozygotes for OCT deficiency. Journal of inherited metabolic disease. 1994; 17(1):133-4. doi: 10.1007/bf00735417. [PMID: 8051924]
  • D Daniewska-Michalska, T Motyl, R Gellert, W Kukulska, M Podgurniak, E Opechowska-Pacocha, K Ostrowski. Efficiency of hemodialysis of pyrimidine compounds in patients with chronic renal failure. Nephron. 1993; 64(2):193-7. doi: 10.1159/000187313. [PMID: 8321350]
  • A B Burlina, V Ferrari, C Dionisi-Vici, A Bordugo, F Zacchello, M Tuchman. Allopurinol challenge test in children. Journal of inherited metabolic disease. 1992; 15(5):707-12. doi: 10.1007/bf01800010. [PMID: 1434508]
  • H A Simmonds, S Reiter, P M Davies, J S Cameron. Orotidine accumulation in human erythrocytes during allopurinol therapy: association with high urinary oxypurinol-7-riboside concentrations in renal failure and in the Lesch-Nyhan syndrome. Clinical science (London, England : 1979). 1991 Mar; 80(3):191-7. doi: 10.1042/cs0800191. [PMID: 1850677]
  • K Kidouchi, C Nakamura, T Katoh, T Kibe, S Ohba, Y Wada. Automated quantitative analysis for orotidine and uridine/thymine in urine by high-performance liquid chromatography with column switching. Advances in experimental medicine and biology. 1991; 309B(?):31-4. doi: 10.1007/978-1-4615-7703-4_7. [PMID: 1781387]
  • M Tuchman. Allopurinol-induced orotidinuria. The New England journal of medicine. 1990 Nov; 323(19):1352-3. doi: NULL. [PMID: 2215627]
  • E R Hauser, J E Finkelstein, D Valle, S W Brusilow. Allopurinol-induced orotidinuria. A test for mutations at the ornithine carbamoyltransferase locus in women. The New England journal of medicine. 1990 Jun; 322(23):1641-5. doi: 10.1056/nejm199006073222305. [PMID: 2342523]
  • A L Horwich, W A Fenton. Precarious balance of nitrogen metabolism in women with a urea-cycle defect. The New England journal of medicine. 1990 Jun; 322(23):1668-70. doi: 10.1056/nejm199006073222310. [PMID: 2342527]
  • A E MacKenzie, H L MacLeod, H M Heick, R G Korneluk. False positive results from the alanine loading test for ornithine carbamoyltransferase deficiency heterozygosity. The Journal of pediatrics. 1989 Oct; 115(4):605-8. doi: 10.1016/s0022-3476(89)80294-x. [PMID: 2795358]
  • S W Brusilow, E Hauser. Simple method of measurement of orotic acid and orotidine in urine. Journal of chromatography. 1989 Sep; 493(2):388-91. doi: 10.1016/s0378-4347(00)82746-2. [PMID: 2584305]
  • T Kojima, T Nishina, M Kitamura, N Kamatani, K Nishioka. Liquid chromatography with multichannel ultraviolet detection used for studying disorders of purine metabolism. Clinical chemistry. 1987 Nov; 33(11):2052-6. doi: NULL. [PMID: 3677379]
  • S Reiter, W Löffler, W Gröbner, N Zöllner. Urinary oxipurinol-1-riboside excretion and allopurinol-induced oroticaciduria. Advances in experimental medicine and biology. 1986; 195 Pt A(?):453-60. doi: 10.1007/978-1-4684-5104-7_75. [PMID: 3728178]
  • H Miyazaki, Y Matsunaga, K Yoshida, S Arakawa, M Hashimoto. Simultaneous determination of plasma and urinary uric acid, xanthine, hypoxanthine, allopurinol, oxipurinol, orotic acid, orotidine and creatinine by high-performance liquid chromatography. Journal of chromatography. 1983 May; 274(?):75-85. doi: 10.1016/s0378-4347(00)84410-2. [PMID: 6874855]
  • M L Harris, V G Oberholzer. Conditions affecting the colorimetry of orotic acid and orotidine in urine. Clinical chemistry. 1980 Mar; 26(3):473-9. doi: NULL. [PMID: 7363468]
  • W J Tax, J H Veerkamp, E D Schretlen. The urinary excretion of orotic acid and orotidine, measured by an isotope dilution assay. Clinica chimica acta; international journal of clinical chemistry. 1978 Dec; 90(3):217-23. doi: 10.1016/0009-8981(78)90260-7. [PMID: 365397]
  • S WEISSMAN, V H BONO, M LEWIS. METABOLIC INERTNESS OF OROTIDINE IN MAN AND THE RAT. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1963 Dec; 114(?):682-5. doi: 10.3181/00379727-114-28769. [PMID: 14120323]
  • V HABERMANN. Elimination by the urine of orotic acid and orotidine in man after application of 6-azauracil. Biochimica et biophysica acta. 1960 Sep; 43(?):137-8. doi: 10.1016/0006-3002(60)90420-0. [PMID: 13710251]