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5988-19-2,MFCD00085339
Catalog No.:AA00IAJR

5988-19-2 | (4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid

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250mg
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$6.00   $4.00
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1g
95%
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$18.00   $13.00
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5g
95%
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$34.00   $24.00
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25g
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100g
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00IAJR
Chemical Name:
(4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid
CAS Number:
5988-19-2
Molecular Formula:
C5H6N2O4
Molecular Weight:
158.1121
MDL Number:
MFCD00085339
SMILES:
O=C1NC(=O)N[C@@H](C1)C(=O)O
Properties
Properties
 
BP:
283.16°C (rough estimate)  
Form:
Solid  
MP:
254-255 °C (dec.);(lit.);  
Refractive Index:
1.5090 (estimate)  
Storage:
Room Temperature;  

Computed Properties
 
Complexity:
225  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
1  
XLogP3:
-1.5  

Upstream Synthesis Route

[1]Biochem.biophys.Acta,1953,vol.12,p.223,227

[1]ChemicalandPharmaceuticalBulletin,1989,vol.37,#7,p.1764-1769

Downstream Synthesis Route

[1],1953,vol.12,p.223,227

74-89-5    5988-19-2   
(S)-N1,N4-Dimethyl-2-ureido-succinamide 

[1]ChemistryofHeterocyclicCompounds,1972,vol.8,p.1032-1036    KhimiyaGeterotsiklicheskikhSoedinenii,1972,vol.8,p.1141-1145

[1]ChemicalandPharmaceuticalBulletin,1989,vol.37,p.1764-1769

His-Pro-NH2*2HBr 
  5988-19-2   
(S)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylicacid(S)-2-((S)-2-carbamoyl-pyrrolidin-1-yl)-1-(1H-imidazol-2-ylmethyl)-2-oxo-ethyl-amide 

[1]JournalofMedicinalChemistry,1990,vol.33,p.2130-2137

[1]ChemicalandPharmaceuticalBulletin,1989,vol.37,p.1764-1769

Literature

Title: Miller (Genee-Wiedemann) syndrome represents a clinically and biochemically distinct subgroup of postaxial acrofacial dysostosis associated with partial deficiency of DHODH.

Journal: Human molecular genetics 20120915

Title: Biochemical and molecular characterization of the pyrimidine biosynthetic enzyme dihydroorotate dehydrogenase from Toxoplasma gondii.

Journal: Molecular and biochemical parasitology 20120801

Title: Stitching together multiple data dimensions reveals interacting metabolomic and transcriptomic networks that modulate cell regulation.

Journal: PLoS biology 20120401

Title: Site directed spin labeling studies of Escherichia coli dihydroorotate dehydrogenase N-terminal extension.

Journal: Biochemical and biophysical research communications 20111028

Title: Chemical rescue of malaria parasites lacking an apicoplast defines organelle function in blood-stage Plasmodium falciparum.

Journal: PLoS biology 20110801

Title: Substrate binding and reactivity are not linked: grafting a proton-transfer network into a Class 1A dihydroorotate dehydrogenase.

Journal: Biochemistry 20110412

Title: Path finding methods accounting for stoichiometry in metabolic networks.

Journal: Genome biology 20110101

Title: Kinetic mechanism and catalysis of Trypanosoma cruzi dihydroorotate dehydrogenase enzyme evaluated by isothermal titration calorimetry.

Journal: Analytical biochemistry 20100401

Title: Development and analysis of an in vivo-compatible metabolic network of Mycobacterium tuberculosis.

Journal: BMC systems biology 20100101

Title: [Development of anti-trypanosome drugs targeting nucleotides biosynthesis and red-ox regulatory pathway].

Journal: Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20090901

Title: Roles in binding and chemistry for conserved active site residues in the class 2 dihydroorotate dehydrogenase from Escherichia coli.

Journal: Biochemistry 20090804

Title: Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli.

Journal: Nature chemical biology 20090801

Title: Dihydroorotase from the hyperthermophile Aquifex aeolicus is activated by stoichiometric association with aspartate transcarbamoylase and forms a one-pot reactor for pyrimidine biosynthesis.

Journal: Biochemistry 20090203

Title: Structures of Trypanosoma cruzi dihydroorotate dehydrogenase complexed with substrates and products: atomic resolution insights into mechanisms of dihydroorotate oxidation and fumarate reduction.

Journal: Biochemistry 20081014

Title: Mutations of RNA polymerase II activate key genes of the nucleoside triphosphate biosynthetic pathways.

Journal: The EMBO journal 20080917

Title: The structures of human dihydroorotate dehydrogenase with and without inhibitor reveal conformational flexibility in the inhibitor and substrate binding sites.

Journal: Biochemistry 20080826

Title: Mutations in yhiT enable utilization of exogenous pyrimidine intermediates in Salmonella enterica serovar Typhimurium.

Journal: Microbiology (Reading, England) 20070801

Title: Mechanism of flavin reduction in class 2 dihydroorotate dehydrogenases.

Journal: Biochemistry 20061219

Title: Thermodynamic analysis of catalysis by the dihydroorotases from hamster and Bacillus caldolyticus, as compared with the uncatalyzed reaction.

Journal: Biochemistry 20060711

Title: Lys-D48 is required for charge stabilization, rapid flavin reduction, and internal electron transfer in the catalytic cycle of dihydroorotate dehydrogenase B of Lactococcus lactis.

Journal: The Journal of biological chemistry 20060630

Title: 13C and 15N isotope effects for conversion of L-dihydroorotate to N-carbamyl-L-aspartate using dihydroorotase from hamster and Bacillus caldolyticus.

Journal: Biochemistry 20060613

Title: Genetic diversity and kinetic properties of Trypanosoma cruzi dihydroorotate dehydrogenase isoforms.

Journal: Parasitology international 20060301

Title: Rate of promoter class turn-over in yeast evolution.

Journal: BMC evolutionary biology 20060101

Title: Immunotherapy for De Novo renal transplantation: what's in the pipeline?

Journal: Drugs 20060101

Title: Dihydroorotase from Escherichia coli: loop movement and cooperativity between subunits.

Journal: Journal of molecular biology 20050506

Title: Mechanism of the dihydroorotase reaction.

Journal: Biochemistry 20041228

Title: Thermodynamic basis of electron transfer in dihydroorotate dehydrogenase B from Lactococcus lactis: analysis by potentiometry, EPR spectroscopy, and ENDOR spectroscopy.

Journal: Biochemistry 20040601

Title: Thorpe-Ingold effects in cyclizations to five-membered and six-membered rings containing planar segments. The rearrangement of N(1)-alkyl-substituted dihydroorotic acids to hydantoinacetic acids in base.

Journal: Organic & biomolecular chemistry 20040407

Title: Inhibitor binding in a class 2 dihydroorotate dehydrogenase causes variations in the membrane-associated N-terminal domain.

Journal: Protein science : a publication of the Protein Society 20040401

Title: Lactococcus lactis dihydroorotate dehydrogenase A mutants reveal important facets of the enzymatic function.

Journal: The Journal of biological chemistry 20030801

Title: Anti-HIV-1 activity of leflunomide: a comparison with mycophenolic acid and hydroxyurea.

Journal: AIDS (London, England) 20030725

Title: Isolation of mitochondria from Plasmodium falciparum showing dihydroorotate dependent respiration.

Journal: Parasitology international 20011101

Title: Dihydrooxonate is a substrate of dihydroorotate dehydrogenase (DHOD) providing evidence for involvement of cysteine and serine residues in base catalysis.

Journal: Archives of biochemistry and biophysics 20010715

Title: Contribution of the bacterial endosymbiont to the biosynthesis of pyrimidine nucleotides in the deep-sea tube worm Riftia pachyptila.

Journal: The Journal of biological chemistry 20010629

Title: St. Louis, Missouri,et al. ENZYMATIC SYNTHESIS AND BREAKDOWN OF A PYRIMIDINE, OROTIC ACID.October 28, 1953.

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Tags:5988-19-2 Molecular Formula|5988-19-2 MDL|5988-19-2 SMILES|5988-19-2 (4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid