Hydroorotic acid

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 597035

CAS#: 155-54-4

Description: Hydroorotic acid is a derivative of orotic acid which serves as an intermediate in pyrimidine biosynthesis.

Chemical Structure

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Hydroorotic acid
CAS# 155-54-4
Instruction

Theoretical Analysis

MedKoo Cat#: 597035
Name: Hydroorotic acid
CAS#: 155-54-4
Chemical Formula: C5H6N2O4
Exact Mass: 158.03
Molecular Weight: 158.110
Elemental Analysis: C, 37.98; H, 3.83; N, 17.72; O, 40.47

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Hydroorotic acid; Dihydroorotic acid;

IUPAC/Chemical Name: 2,6-dioxohexahydropyrimidine-4-carboxylic acid

InChi Key: UFIVEPVSAGBUSI-UHFFFAOYSA-N

InChi Code: InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)

SMILES Code: O=C(NC(C1)=O)NC1C(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: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 158.11 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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3: Alves CN, Silva JR, Roitberg AE. Insights into the mechanism of oxidation of dihydroorotate to orotate catalysed by human class 2 dihydroorotate dehydrogenase: a QM/MM free energy study. Phys Chem Chem Phys. 2015 Jul 21;17(27):17790-6. doi: 10.1039/c5cp02016f. Epub 2015 Jun 19. PubMed PMID: 26087682.

4: Peng WF, Huang CY. Allantoinase and dihydroorotase binding and inhibition by flavonols and the substrates of cyclic amidohydrolases. Biochimie. 2014 Jun;101:113-22. doi: 10.1016/j.biochi.2014.01.001. Epub 2014 Jan 10. PubMed PMID: 24418229.

5: Silva Nde F, Lameira J, Alves CN, Martí S. Computational study of the mechanism of half-reactions in class 1A dihydroorotate dehydrogenase from Trypanosoma cruzi. Phys Chem Chem Phys. 2013 Nov 21;15(43):18863-71. doi: 10.1039/c3cp52692e. PubMed PMID: 24084894.

6: Hegewald J, Gross U, Bohne W. Identification of dihydroorotate dehydrogenase as a relevant drug target for 1-hydroxyquinolones in Toxoplasma gondii. Mol Biochem Parasitol. 2013 Jul;190(1):6-15. doi: 10.1016/j.molbiopara.2013.05.008. Epub 2013 Jun 5. PubMed PMID: 23747278.

7: Leung K. (68)Ga-1,4,7-Triazacyclononane,1-glutaric acid-4,7-acetic acid-Cpa-cyclo(d-Cys-amino-Phe-hydroorotic acid-D-4-amino-Phe(carbamoyl)-Lys-Thr-Cys)-D-Tyr-NH(2) (JR11). 2012 Oct 5 [updated 2013 Jan 3]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK115433/ PubMed PMID: 23304757.

8: Leung K. (68)Ga-1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid-Cpa-cyclo(d-Cys-amino-Phe-hydroorotic acid-D-4-amino-Phe(carbamoyl)-Lys-Thr-Cys)-D-Tyr-NH(2) (JR11). 2012 Oct 7 [updated 2013 Jan 3]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK115431/ PubMed PMID: 23304755.

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10: Hortua Triana MA, Huynh MH, Garavito MF, Fox BA, Bzik DJ, Carruthers VB, Löffler M, Zimmermann BH. Biochemical and molecular characterization of the pyrimidine biosynthetic enzyme dihydroorotate dehydrogenase from Toxoplasma gondii. Mol Biochem Parasitol. 2012 Aug;184(2):71-81. doi: 10.1016/j.molbiopara.2012.04.009. Epub 2012 May 8. PubMed PMID: 22580100; PubMed Central PMCID: PMC3855825.

11: Couto SG, Cristina Nonato M, Costa-Filho AJ. Site directed spin labeling studies of Escherichia coli dihydroorotate dehydrogenase N-terminal extension. Biochem Biophys Res Commun. 2011 Oct 28;414(3):487-92. doi: 10.1016/j.bbrc.2011.09.092. Epub 2011 Oct 2. PubMed PMID: 21986535.

12: McDonald CA, Palfey BA. Substrate binding and reactivity are not linked: grafting a proton-transfer network into a Class 1A dihydroorotate dehydrogenase. Biochemistry. 2011 Apr 12;50(14):2714-6. doi: 10.1021/bi200258y. Epub 2011 Mar 21. PubMed PMID: 21401078; PubMed Central PMCID: PMC3077728.

13: Cheleski J, Wiggers HJ, Citadini AP, da Costa Filho AJ, Nonato MC, Montanari CA. Kinetic mechanism and catalysis of Trypanosoma cruzi dihydroorotate dehydrogenase enzyme evaluated by isothermal titration calorimetry. Anal Biochem. 2010 Apr 1;399(1):13-22. doi: 10.1016/j.ab.2009.11.018. Epub 2009 Nov 20. PubMed PMID: 19932077.

14: Kita K, Inaoka DK, Harada S. [Development of anti-trypanosome drugs targeting nucleotides biosynthesis and red-ox regulatory pathway]. Tanpakushitsu Kakusan Koso. 2009 Sep;54(12 Suppl):1676-83. Review. Japanese. PubMed PMID: 21089606.

15: Fagan RL, Palfey BA. Roles in binding and chemistry for conserved active site residues in the class 2 dihydroorotate dehydrogenase from Escherichia coli. Biochemistry. 2009 Aug 4;48(30):7169-78. doi: 10.1021/bi900370s. PubMed PMID: 19530672; PubMed Central PMCID: PMC2800825.

16: Zhang P, Martin PD, Purcarea C, Vaishnav A, Brunzelle JS, Fernando R, Guy-Evans HI, Evans DR, Edwards BF. Dihydroorotase from the hyperthermophile Aquifex aeolicus is activated by stoichiometric association with aspartate transcarbamoylase and forms a one-pot reactor for pyrimidine biosynthesis. Biochemistry. 2009 Feb 3;48(4):766-78. doi: 10.1021/bi801831r. PubMed PMID: 19128030; PubMed Central PMCID: PMC3863388.

17: Inaoka DK, Sakamoto K, Shimizu H, Shiba T, Kurisu G, Nara T, Aoki T, Kita K, Harada S. Structures of Trypanosoma cruzi dihydroorotate dehydrogenase complexed with substrates and products: atomic resolution insights into mechanisms of dihydroorotate oxidation and fumarate reduction. Biochemistry. 2008 Oct 14;47(41):10881-91. doi: 10.1021/bi800413r. Epub 2008 Sep 23. PubMed PMID: 18808149.

18: Walse B, Dufe VT, Svensson B, Fritzson I, Dahlberg L, Khairoullina A, Wellmar U, Al-Karadaghi S. The structures of human dihydroorotate dehydrogenase with and without inhibitor reveal conformational flexibility in the inhibitor and substrate binding sites. Biochemistry. 2008 Aug 26;47(34):8929-36. doi: 10.1021/bi8003318. Epub 2008 Aug 2. PubMed PMID: 18672895.

19: Zaharik ML, Lamb SS, Baker KE, Krogan NJ, Neuhard J, Kelln RA. Mutations in yhiT enable utilization of exogenous pyrimidine intermediates in Salmonella enterica serovar Typhimurium. Microbiology. 2007 Aug;153(Pt 8):2472-82. PubMed PMID: 17660412.

20: Fagan RL, Nelson MN, Pagano PM, Palfey BA. Mechanism of flavin reduction in class 2 dihydroorotate dehydrogenases. Biochemistry. 2006 Dec 19;45(50):14926-32. PubMed PMID: 17154530.