Hydroorotic acid, L- | CAS#5988-19-2 | precursor to the biological pyrimidines

Hydroorotic acid, L-
featured

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

MedKoo CAT#: 596552

CAS#: 5988-19-2

Description: Hydroorotic acid, L-is a precursor to the biological pyrimidines, such as thymine, uracil, cytosine and hydroxymethylcytosine. When employed in large amounts D-dihydroorotic acid is an antimetabolite of L-dihydroorotic acid in pyrimidine utilization. It has also been found to inhibit the orotic acid utilization of those organisms which have a requirement for it in order to grow. In general it may be said to inhibit bacterial growth.

Chemical Structure

Hydroorotic acid, L-

CAS# 5988-19-2

Instruction

Theoretical Analysis

MedKoo Cat#: 596552
Name: Hydroorotic acid, L-
CAS#: 5988-19-2
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

Size	Price	Availability
1g	USD 250	2 Weeks
5g	USD 450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Hydroorotic acid, L-; L-Dihydroorotate; L-Dihydroorotic acid; Hydroorotic acid L-form;

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

InChi Key: UFIVEPVSAGBUSI-REOHCLBHSA-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)/t2-/m0/s1

SMILES Code: O=C([C@H](CC(N1)=O)NC1=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:

Instruction:

View handling instruction

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.

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:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

1: Tiwari K, Kumar R, Dubey VK. Biochemical characterization of dihydroorotase of Leishmania donovani: Understanding pyrimidine metabolism through its inhibition. Biochimie. 2016 Dec;131:45-53. doi: 10.1016/j.biochi.2016.09.009. Epub 2016 Sep 17. PubMed PMID: 27650727.

2: 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.

3: 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.

4: 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.

5: Huang DT, Kaplan J, Menz RI, Katis VL, Wake RG, Zhao F, Wolfenden R, Christopherson RI. Thermodynamic analysis of catalysis by the dihydroorotases from hamster and Bacillus caldolyticus, as compared with the uncatalyzed reaction. Biochemistry. 2006 Jul 11;45(27):8275-83. PubMed PMID: 16819826.

6: Anderson MA, Cleland WW, Huang DT, Chan C, Shojaei M, Christopherson RI. 13C and 15N isotope effects for conversion of L-dihydroorotate to N-carbamyl-L-aspartate using dihydroorotase from hamster and Bacillus caldolyticus. Biochemistry. 2006 Jun 13;45(23):7132-9. PubMed PMID: 16752903.

7: Lee M, Chan CW, Mitchell Guss J, Christopherson RI, Maher MJ. Dihydroorotase from Escherichia coli: loop movement and cooperativity between subunits. J Mol Biol. 2005 May 6;348(3):523-33. PubMed PMID: 15826651.

8: Marcinkeviciene J, Jiang W, Locke G, Kopcho LM, Rogers MJ, Copeland RA. A second dihydroorotate dehydrogenase (Type A) of the human pathogen Enterococcus faecalis: expression, purification, and steady-state kinetic mechanism. Arch Biochem Biophys. 2000 May 1;377(1):178-86. PubMed PMID: 10775458.

9: Fairbanks LD, Carrey EA, Rückemann K, Swaminathan R, Kirschbaum B, Simmonds HA. Simultaneous separation by high-performance liquid chromatography of carbamoyl aspartate, carbamoyl phosphate and dihydroorotic acid. J Chromatogr B Biomed Sci Appl. 1999 Sep 24;732(2):487-93. PubMed PMID: 10517371.

10: Cleaveland ES, Zaharevitz DW, Kelley JA, Paull K, Cooney DA, Ford H Jr. Identification of a novel inhibitor (NSC 665564) of dihydroorotate dehydrogenase with a potency equivalent to brequinar. Biochem Biophys Res Commun. 1996 Jun 25;223(3):654-9. PubMed PMID: 8687451.

11: Suzuki M, Sugano H, Matsumoto K, Yamamura M, Ishida R. Synthesis and central nervous system actions of thyrotropin-releasing hormone analogues containing a dihydroorotic acid moiety. J Med Chem. 1990 Aug;33(8):2130-7. PubMed PMID: 2115588.

12: Krungkrai J, Cerami A, Henderson GB. Pyrimidine biosynthesis in parasitic protozoa: purification of a monofunctional dihydroorotase from Plasmodium berghei and Crithidia fasciculata. Biochemistry. 1990 Jul 3;29(26):6270-5. PubMed PMID: 1976382.

13: Lee MH, Cowling RA, Sander EG, Pettigrew DW. Bovine liver dihydropyrimidine amidohydrolase: pH dependencies of inactivation by chelators and steady-state kinetic properties. Arch Biochem Biophys. 1986 Jul;248(1):368-78. PubMed PMID: 3089167.

14: Pettigrew DW, Mehta BJ, Bidigare RR, Choudhury RR, Scheffler JE, Sander EG. Enzyme elements involved in the interconversion of L-carbamylaspartate and L-dihydroorotate by dihydroorotase from Clostridium oroticum. Arch Biochem Biophys. 1985 Dec;243(2):447-53. PubMed PMID: 2867744.

15: Kensler TW, Cooney DA, Jayaram HN, Schaeffer C, Choie DD. A facile tritium release assay for mammalian L-dihydroorotate dehydrogenase. Anal Biochem. 1981 Nov 1;117(2):315-9. PubMed PMID: 6275738.

16: Kensler TW, Han N, Cooney DA. A straightforward method for the simultaneous preparation of radiolabeled L-dihydroörotic and N-carbamyl-L-aspartic acids. Anal Biochem. 1981 Feb;111(1):49-53. PubMed PMID: 7235240.

17: Christopherson RI, Jones ME. The overall synthesis of L-5,6-dihydroorotate by multienzymatic protein pyr1-3 from hamster cells. Kinetic studies, substrate channeling, and the effects of inhibitors. J Biol Chem. 1980 Dec 10;255(23):11381-95. PubMed PMID: 6108323.

18: Durschlag RP, Robinson JL. Orotic acid-induced metabolic changes in the rat. J Nutr. 1980 Apr;110(4):816-21. PubMed PMID: 7365548.

19: TAYLOR WH, TAYLOR ML. ENZYMES OF THE PYRIMIDINE PATHWAY IN ESCHERICHIA COLI. II. INTRACELLULAR LOCALIZATION AND PROPERTIES OF DIHYDROOROTIC DEHYDROGENASE. J Bacteriol. 1964 Jul;88:105-10. PubMed PMID: 14197872; PubMed Central PMCID: PMC277264.

Your view history

Hydroorotic acid, L- featured