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Orotic acid

CAS No.:
65-86-1
Catalog Number:
AG0035FO
Molecular Formula:
C5H4N2O4
Molecular Weight:
156.0963
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5g
98%
In Stock USA
United States
$13
- +
25g
98%
In Stock USA
United States
$25
- +
100g
98%
In Stock USA
United States
$63
- +
500g
98%
In Stock USA
United States
$188
- +
Product Description
Catalog Number:
AG0035FO
Chemical Name:
Orotic acid
CAS Number:
65-86-1
Molecular Formula:
C5H4N2O4
Molecular Weight:
156.0963
MDL Number:
MFCD00149398
IUPAC Name:
2,4-dioxo-1H-pyrimidine-6-carboxylic acid
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)
InChI Key:
PXQPEWDEAKTCGB-UHFFFAOYSA-N
SMILES:
O=c1[nH]c(=O)[nH]c(c1)C(=O)O
EC Number:
200-619-8
UNII:
61H4T033E5
Properties
Complexity:
268  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
156.017g/mol
Formal Charge:
0
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
156.097g/mol
Monoisotopic Mass:
156.017g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
95.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.4  
Literature
Title Journal
Orotic acid induces hypertension associated with impaired endothelial nitric oxide synthesis. Toxicological sciences : an official journal of the Society of Toxicology 20150401
Dehydroepiandrosterone sulfate and cytochrome P450 inducers alleviate fatty liver in male rats fed an orotic acid-supplemented diet. The Journal of toxicological sciences 20150401
Benzoic acid and specific 2-oxo acids activate hepatic efflux of glutamate at OAT2. Biochimica et biophysica acta 20130201
Solid state simulation of tetramer form of 5-aminoorotic acid: the vibrational spectra and molecular structure study by using MP2 and DFT calculations. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20121101
EDTA disodium zinc has superior bioavailability compared to common inorganic or chelated zinc compounds in rats fed a high phytic acid diet. Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS) 20121001
Selenium and zinc internalized by Lactobacillus buchneri Lb26 (DSM 16341) and Bifidobacterium lactis Bb1 (DSM 17850): improved bioavailability using a new biological approach. Journal of clinical gastroenterology 20121001
Miller (Genee-Wiedemann) syndrome represents a clinically and biochemically distinct subgroup of postaxial acrofacial dysostosis associated with partial deficiency of DHODH. Human molecular genetics 20120915
Ion-exclusion chromatography determination of organic acid in uridine 5'-monophosphate fermentation broth. Journal of chromatographic science 20120901
D282, a non-nucleoside inhibitor of influenza virus infection that interferes with de novo pyrimidine biosynthesis. Antiviral chemistry & chemotherapy 20120821
Crystal structure of dihydroorotate dehydrogenase from Leishmania major. Biochimie 20120801
Biochemical and molecular characterization of the pyrimidine biosynthetic enzyme dihydroorotate dehydrogenase from Toxoplasma gondii. Molecular and biochemical parasitology 20120801
Pyrimidin-2(1H)-ones based inhibitors of Mycobacterium tuberculosis orotate phosphoribosyltransferase. European journal of medicinal chemistry 20120801
Enhanced uridine 5'-monophosphate production by whole cell of Saccharomyces cerevisiae through rational redistribution of metabolic flux. Bioprocess and biosystems engineering 20120601
Secondary processes in atmospheric pressure chemical ionization-ion trap mass spectrometry: a case study of orotic acid. Journal of mass spectrometry : JMS 20120601
Hyperammonemia in a patient with late-onset ornithine carbamoyltransferase deficiency. Journal of Korean medical science 20120501
Genetic dissection of pyrimidine biosynthesis and salvage in Leishmania donovani. The Journal of biological chemistry 20120413
Improvement of the energy supply and contractile function in normal and ischemic rat hearts by dietary orotic acid. Life sciences 20120409
Sustained correction of OTC deficiency in spf( ash) mice using optimized self-complementary AAV2/8 vectors. Gene therapy 20120401
Current advances in detection and treatment of babesiosis. Current medicinal chemistry 20120401
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Cytochrome b mutation Y268S conferring atovaquone resistance phenotype in malaria parasite results in reduced parasite bc1 catalytic turnover and protein expression. The Journal of biological chemistry 20120323
Preparation and chromatographic evaluation of a cysteine-bonded zwitterionic hydrophilic interaction liquid chromatography stationary phase. Journal of chromatography. A 20120309
Path-integral calculations of heavy atom kinetic isotope effects in condensed phase reactions using higher-order Trotter factorizations. Journal of computational chemistry 20120205
Reference intervals for orotic acid in urine, plasma and dried blood spot using hydrophilic interaction liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120201
Growth and exopolysaccharide yield of Lactobacillus delbrueckii ssp. bulgaricus DSM 20081 in batch and continuous bioreactor experiments at constant pH. Journal of bioscience and bioengineering 20120201
Molecular, kinetic and thermodynamic characterization of Mycobacterium tuberculosis orotate phosphoribosyltransferase. Molecular bioSystems 20120201
Preclinical evaluation of a clinical candidate AAV8 vector for ornithine transcarbamylase (OTC) deficiency reveals functional enzyme from each persisting vector genome. Molecular genetics and metabolism 20120201
Crystallization and preliminary X-ray diffraction analysis of orotate phosphoribosyltransferase from the human malaria parasite Plasmodium falciparum. Acta crystallographica. Section F, Structural biology and crystallization communications 20120201
Conformational studies of hydantoin-5-acetic acid and orotic acid. Acta crystallographica. Section C, Crystal structure communications 20120201
[The ileocoecal valve changes in chronic constipation in children]. Klinichna khirurhiia 20120201
Mitochondria-ros crosstalk in the control of cell death and aging. Journal of signal transduction 20120101
Functional Relationships between Lipid Metabolism and Liver Regeneration. International journal of hepatology 20120101
Reconstruction and analysis of a genome-scale metabolic model for Scheffersomyces stipitis. Microbial cell factories 20120101
Sex-specific mouse liver gene expression: genome-wide analysis of developmental changes from pre-pubertal period to young adulthood. Biology of sex differences 20120101
Dietary sea cucumber cerebroside alleviates orotic acid-induced excess hepatic adipopexis in rats. Lipids in health and disease 20120101
Cholesterol-lowering probiotics as potential biotherapeutics for metabolic diseases. Experimental diabetes research 20120101
[Correction of a connective tissue dysplasia in the treatment of postoperative abdominal hernias]. Klinichna khirurhiia 20120101
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The association of dietary intake of purine-rich vegetables, sugar-sweetened beverages and dairy with plasma urate, in a cross-sectional study. PloS one 20120101
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 20120101
Carboxyamidotriazole-orotate inhibits the growth of imatinib-resistant chronic myeloid leukaemia cells and modulates exosomes-stimulated angiogenesis. PloS one 20120101
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The major roles of DNA polymerases epsilon and delta at the eukaryotic replication fork are evolutionarily conserved. PLoS genetics 20111201
Site directed spin labeling studies of Escherichia coli dihydroorotate dehydrogenase N-terminal extension. Biochemical and biophysical research communications 20111028
Crystallographic snapshots of tyrosine phenol-lyase show that substrate strain plays a role in C-C bond cleavage. Journal of the American Chemical Society 20111019
Mechanism of the orotidine 5'-monophosphate decarboxylase-catalyzed reaction: importance of residues in the orotate binding site. Biochemistry 20111004
Megaloblastic anemia--a rare cause. Indian journal of pediatrics 20111001
Acute treatment of hyperammonemia by continuous renal replacement therapy in a newborn patient with ornithine transcarbamylase deficiency. Korean journal of pediatrics 20111001
Type II Toxoplasma gondii KU80 knockout strains enable functional analysis of genes required for cyst development and latent infection. Eukaryotic cell 20110901
The function of oxalic acid in the human metabolism. Clinical chemistry and laboratory medicine 20110901
Role of the AMPK/SREBP-1 pathway in the development of orotic acid-induced fatty liver. Journal of lipid research 20110901
Anti-tumor activity of liposome encapsulated fluoroorotic acid as a single agent and in combination with liposome irinotecan. Journal of controlled release : official journal of the Controlled Release Society 20110810
Perinatal gene transfer to the liver. Current pharmaceutical design 20110801
Plastid uridine salvage activity is required for photoassimilate allocation and partitioning in Arabidopsis. The Plant cell 20110801
Development of pyrF-based gene knockout systems for genome-wide manipulation of the archaea Haloferax mediterranei and Haloarcula hispanica. Journal of genetics and genomics = Yi chuan xue bao 20110620
A GC/MS-based metabolomic approach for diagnosing citrin deficiency. Analytical and bioanalytical chemistry 20110601
OAT2 catalyses efflux of glutamate and uptake of orotic acid. The Biochemical journal 20110601
Study on possible mechanism of orotic acid-induced fatty liver in rats. Nutrition (Burbank, Los Angeles County, Calif.) 20110501
Human urate transporter 1 (hURAT1) mediates the transport of orotate. The journal of physiological sciences : JPS 20110501
Identification of the UMP synthase gene by establishment of uracil auxotrophic mutants and the phenotypic complementation system in the marine diatom Phaeodactylum tricornutum. Plant physiology 20110501
Induction and prevention of severe hyperammonemia in the spfash mouse model of ornithine transcarbamylase deficiency using shRNA and rAAV-mediated gene delivery. Molecular therapy : the journal of the American Society of Gene Therapy 20110501
Analysis of the efficacy, safety, and regulatory status of novel forms of creatine. Amino acids 20110501
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Substrate binding and reactivity are not linked: grafting a proton-transfer network into a Class 1A dihydroorotate dehydrogenase. Biochemistry 20110412
A common telomeric gene silencing assay is affected by nucleotide metabolism. Molecular cell 20110408
Molecular recognition of melamine by vesicles spontaneously formed from orotic acid derived bolaamphiphiles. The journal of physical chemistry. B 20110303
Quinolones: from antibiotics to autoinducers. FEMS microbiology reviews 20110301
New insights into galactose metabolism by Schizosaccharomyces pombe: isolation and characterization of a galactose-assimilating mutant. Journal of bioscience and bioengineering 20110201
Structure of the putative dihydroorotate dehydrogenase from Streptococcus mutans. Acta crystallographica. Section F, Structural biology and crystallization communications 20110201
Sirt3 promotes the urea cycle and fatty acid oxidation during dietary restriction. Molecular cell 20110121
Brassinolide-improved development of Brassica napus microspore-derived embryos is associated with increased activities of purine and pyrimidine salvage pathways. Planta 20110101
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3D-QSAR studies on a series of dihydroorotate dehydrogenase inhibitors: analogues of the active metabolite of leflunomide. International journal of molecular sciences 20110101
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A Caenorhabditis elegans model of orotic aciduria reveals enlarged lysosome-related organelles in embryos lacking umps-1 function. The FEBS journal 20100301
Orotic acid quantification in dried blood spots and biological fluids by hydrophilic interaction liquid chromatography tandem mass spectrometry. Journal of separation science 20100301
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