Orotidine
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MedKoo CAT#: 112029

CAS#: 314-50-1

Description: Orotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a β-N1-glycosidic bond. It is found in bacteria, fungi and plants. It was first isolated in 1951. In humans, orotidine occurs as its 5'-phosphate (orotidylic acid), which is an intermediate in pyrimidine nucleotide biosynthesis (cytidine and uridine) that are found in nucleic acids..


Chemical Structure

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Orotidine
CAS# 314-50-1

Theoretical Analysis

MedKoo Cat#: 112029
Name: Orotidine
CAS#: 314-50-1
Chemical Formula: C10H12N2O8
Exact Mass: 288.0594
Molecular Weight: 288.21
Elemental Analysis: C, 41.67; H, 4.20; N, 9.72; O, 44.41

Price and Availability

Size Price Availability Quantity
1.0mg USD 290.0 2 Weeks
5.0mg USD 760.0 2 Weeks
10.0mg USD 1270.0 2 Weeks
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Synonym: Orotic Acid riboside; 6-carboxy Uridine; 6 carboxy Uridine

IUPAC/Chemical Name: 3-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

InChi Key: FKCRAVPPBFWEJD-XVFCMESISA-N

InChi Code: 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

SMILES Code: OC(C(N(C(N1)=O)[C@@]2(O[C@H](CO)[C@@H](O)[C@H]2O)[H])=CC1=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 50.0 173.48

Preparing Stock Solutions

The following data is based on the product molecular weight 288.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Cristobal JR, Brandão TAS, Reyes AC, Richard JP. Protein-Ribofuranosyl Interactions Activate Orotidine 5'-Monophosphate Decarboxylase for Catalysis. Biochemistry. 2021 Nov 16;60(45):3362-3373. doi: 10.1021/acs.biochem.1c00589. Epub 2021 Nov 2. PMID: 34726391; PMCID: PMC8650221.

2: Fujihashi M, Mnpotra JS, Mishra RK, Pai EF, Kotra LP. Orotidine Monophosphate Decarboxylase--A Fascinating Workhorse Enzyme with Therapeutic Potential. J Genet Genomics. 2015 May 20;42(5):221-34. doi: 10.1016/j.jgg.2015.04.005. Epub 2015 May 16. PMID: 26059770.

3: Brandão TAS, Richard JP. Orotidine 5'-Monophosphate Decarboxylase: The Operation of Active Site Chains Within and Across Protein Subunits. Biochemistry. 2020 Jun 2;59(21):2032-2040. doi: 10.1021/acs.biochem.0c00241. Epub 2020 May 19. PMID: 32374983; PMCID: PMC7476526.

4: Meza-Avina ME, Wei L, Buhendwa MG, Poduch E, Bello AM, Pai EF, Kotra LP. Inhibition of orotidine 5'-monophosphate decarboxylase and its therapeutic potential. Mini Rev Med Chem. 2008 Mar;8(3):239-47. doi: 10.2174/138955708783744065. PMID: 18336344.

5: Kim EK, Martin V, Krishnamurthy R. Orotidine-Containing RNA: Implications for the Hierarchical Selection (Systems Chemistry Emergence) of RNA. Chemistry. 2017 Sep 12;23(51):12668-12675. doi: 10.1002/chem.201702912. Epub 2017 Aug 11. PMID: 28708927; PMCID: PMC6311447.

6: Nyhan WL, Gangoiti JA. Hereditary Orotic Aciduria and the Excretion of Orotidine. Neuropediatrics. 2016 Dec;47(6):408-409. doi: 10.1055/s-0036-1587594. Epub 2016 Aug 30. PMID: 27574833.

7: Zhang L, Zheng X, Cairns TC, Zhang Z, Wang D, Zheng P, Sun J. Disruption or reduced expression of the orotidine-5'-decarboxylase gene pyrG increases citric acid production: a new discovery during recyclable genome editing in Aspergillus niger. Microb Cell Fact. 2020 Mar 24;19(1):76. doi: 10.1186/s12934-020-01334-z. PMID: 32209089; PMCID: PMC7092557.

8: Manhas A, Dubey S, Jha PC. A profound computational study to prioritize the natural compound inhibitors against the P. falciparum orotidine-5-monophosphate decarboxylase enzyme. J Biomol Struct Dyn. 2020 Jun;38(9):2704-2716. doi: 10.1080/07391102.2019.1644197. Epub 2019 Jul 22. PMID: 31304874.

9: Amyes TL, Ming SA, Goldman LM, Wood BM, Desai BJ, Gerlt JA, Richard JP. Orotidine 5'-monophosphate decarboxylase: transition state stabilization from remote protein-phosphodianion interactions. Biochemistry. 2012 Jun 12;51(23):4630-2. doi: 10.1021/bi300585e. Epub 2012 May 31. PMID: 22620855; PMCID: PMC3431445.

10: Kotra LP, Pai EF. Inhibition of orotidine-5'-monophosphate decarboxylase-- discoveries and lessons. Nucleic Acids Symp Ser (Oxf). 2008;(52):85-6. doi: 10.1093/nass/nrn043. PMID: 18776265.

11: Gao J. Catalysis by enzyme conformational change as illustrated by orotidine 5'-monophosphate decarboxylase. Curr Opin Struct Biol. 2003 Apr;13(2):184-92. doi: 10.1016/s0959-440x(03)00041-1. PMID: 12727511.

12: Reyes AC, Amyes TL, Richard JP. Enzyme Architecture: Erection of Active Orotidine 5'-Monophosphate Decarboxylase by Substrate-Induced Conformational Changes. J Am Chem Soc. 2017 Nov 15;139(45):16048-16051. doi: 10.1021/jacs.7b08897. Epub 2017 Nov 1. PMID: 29058891; PMCID: PMC5720041.

13: Begley TP, Appleby TC, Ealick SE. The structural basis for the remarkable catalytic proficiency of orotidine 5'-monophosphate decarboxylase. Curr Opin Struct Biol. 2000 Dec;10(6):711-8. doi: 10.1016/s0959-440x(00)00148-2. PMID: 11114509.

14: Paojinda P, Imprasittichai W, Krungkrai SR, Palacpac NMQ, Horii T, Krungkrai J. Bifunctional activity of fused Plasmodium falciparum orotate phosphoribosyltransferase and orotidine 5'-monophosphate decarboxylase. Parasitol Int. 2018 Feb;67(1):79-84. doi: 10.1016/j.parint.2017.04.003. Epub 2017 Apr 4. PMID: 28389349.

15: Purohit MK, Poduch E, Wei LW, Crandall IE, To T, Kain KC, Pai EF, Kotra LP. Novel cytidine-based orotidine-5'-monophosphate decarboxylase inhibitors with an unusual twist. J Med Chem. 2012 Nov 26;55(22):9988-97. doi: 10.1021/jm301176r. Epub 2012 Oct 18. PMID: 22991951.

16: Novak WRP, West KHJ, Kirkman LMD, Brandt GS. Re-refinement of Plasmodium falciparum orotidine 5'-monophosphate decarboxylase provides a clearer picture of an important malarial drug target. Acta Crystallogr F Struct Biol Commun. 2018 Oct 1;74(Pt 10):664-668. doi: 10.1107/S2053230X18010610. Epub 2018 Sep 21. PMID: 30279319; PMCID: PMC6168774.

17: Simmonds HA, Reiter S, Davies PM, Cameron JS. 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. Clin Sci (Lond). 1991 Mar;80(3):191-7. doi: 10.1042/cs0800191. PMID: 1850677.

18: Bello AM, Konforte D, Poduch E, Furlonger C, Wei L, Liu Y, Lewis M, Pai EF, Paige CJ, Kotra LP. Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents. J Med Chem. 2009 Mar 26;52(6):1648-58. doi: 10.1021/jm801224t. PMID: 19260677.

19: Goryanova B, Spong K, Amyes TL, Richard JP. Catalysis by orotidine 5'-monophosphate decarboxylase: effect of 5-fluoro and 4'-substituents on the decarboxylation of two-part substrates. Biochemistry. 2013 Jan 22;52(3):537-46. doi: 10.1021/bi301650d. Epub 2013 Jan 11. PMID: 23276261; PMCID: PMC3556479.