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Identification
YMDB IDYMDB00405
NameOrotic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionOrotic acid, also known as orotate or orotsaeure, belongs to the class of organic compounds known as pyrimidinecarboxylic acids. These are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring. Orotic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Orotic acid exists in all living species, ranging from bacteria to humans. Within yeast, orotic acid participates in a number of enzymatic reactions. In particular, orotic acid and phosphoribosyl pyrophosphate can be converted into orotidylic acid through the action of the enzyme orotate phosphoribosyltransferase. In addition, ubiquinol-1 and orotic acid can be biosynthesized from 4,5-dihydroorotic acid and ubiquinone-1 through the action of the enzyme dihydroorotate dehydrogenase, type 2. In yeast, orotic acid is involved in the metabolic pathway called the pyrimidine metabolism pathway. Orotic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidecarboxylic acid
  • 2,6-dihydroxy-4-pyrimidinecarboxylic acid
  • 2,6-Dihydroxypyrimidine-4-carboxylic acid
  • 2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid
  • 6-Carboxy-2,4-dihydroxypyrimidine
  • 6-Carboxyuracil
  • 6-Uracilcarboxylic acid
  • Animal galactose factor
  • Lactinium
  • ORO
  • Orodin
  • Oropur
  • Orotate
  • Orotic acid
  • Orotonin
  • Orotonsan
  • Oroturic
  • Orotyl
  • uracil-6-carboxylate
  • Uracil-6-carboxylic acid
  • Vitamin B13
  • Whey factor
  • Orotsaeure
  • 1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
  • 1,2,3,6-Tetrahydro-2,6-dioxopyrimidin-4-carbonsaeure
  • 2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
  • Acide orotique
  • Acido orotico
  • Acidum oroticum
  • Molkensaeure
  • Orotsaure
  • Uracil-6-carbosaeure
  • Zinc orotate
  • Orotate, zinc
  • Acid, orotic
  • Orotate, potassium
  • Potassium orotate
  • Orotate, sodium
  • Sodium orotate
CAS number65-86-1
WeightAverage: 156.0963
Monoisotopic: 156.017106626
InChI KeyPXQPEWDEAKTCGB-UHFFFAOYSA-N
InChIInChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
IUPAC Name2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Traditional IUPAC Nameorotic acid
Chemical FormulaC5H4N2O4
SMILES[H]OC(=O)C1=C([H])C(=O)N([H])C(=O)N1[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidinecarboxylic acids. These are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidinecarboxylic acids
Alternative Parents
Substituents
  • Pyrimidine-6-carboxylic acid
  • Hydropyrimidine carboxylic acid derivative
  • Pyrimidone
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Urea
  • Lactam
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point345.5 °C
Experimental Properties
PropertyValueReference
Water Solubility1.82 mg/mL at 18 oC [YALKOWSKY,SH & HE,Y (2003)]PhysProp
LogP-0.83 [SANGSTER (1994)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.51 g/LALOGPS
logP-0.89ALOGPS
logP-1.2ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.83ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.27 m³·mol⁻¹ChemAxon
Polarizability12.46 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pyrimidine metabolismec00240 Map00240
SMPDB Reactions
Orotic acid + Phosphoribosyl pyrophosphatePyrophosphate + Orotidylic acid
4,5-Dihydroorotic acid + Ubiquinone Q1QH(2) + Orotic acid
KEGG Reactions
Ubiquinone-6 + L-Dihydroorotic acidUbiquinol-6 + Orotic acid
L-Dihydroorotic acid + oxygenOrotic acid + Hydrogen peroxide
Fumaric acid + L-Dihydroorotic acidOrotic acid + Succinic acid
Pyrophosphate + Orotidylic acidOrotic acid + Phosphoribosyl pyrophosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
Synthesis Reference:Mitchell, Herschel K.; Nyc, Joseph F. Intermediates in the synthesis of orotic acid from oxalacetic ester and urea. Journal of the American Chemical Society (1947), 69 674-7.
External Links:
ResourceLink
CHEBI ID16742
HMDB IDHMDB00226
Pubchem Compound ID967
Kegg IDC00295
ChemSpider ID942
FOODB IDFDB012327
WikipediaOrotic_acid
BioCyc IDOROTATE

Enzymes

General function:
Involved in orotate phosphoribosyltransferase activity
Specific function:
Catalyzes the transfer of a ribosyl phosphate group from 5-phosphoribose 1-diphosphate to orotate, leading to the formation of orotidine monophosphate (OMP)
Gene Name:
URA5
Uniprot ID:
P13298
Molecular weight:
24664.19922
Reactions
Orotidine 5'-phosphate + diphosphate → orotate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in orotate phosphoribosyltransferase activity
Specific function:
Catalyzes the transfer of a ribosyl phosphate group from 5-phosphoribose 1-diphosphate to orotate, leading to the formation of orotidine monophosphate (OMP)
Gene Name:
URA10
Uniprot ID:
P30402
Molecular weight:
24810.30078
Reactions
Orotidine 5'-phosphate + diphosphate → orotate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in catalytic activity
Specific function:
In the de novo pyrimidine biosynthesic pathway, catalyzes the stereospecific oxidation of (S)-dihydroorotate to orotate and the reduction of fumarate to succinate. Does not use oxaloacetate and NAD or NADP as electron acceptors
Gene Name:
URA1
Uniprot ID:
P28272
Molecular weight:
34800.60156
Reactions
(S)-dihydroorotate + O(2) → orotate + H(2)O(2).
(S)-dihydroorotate + a quinone → orotate + a quinol