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Identification
YMDB IDYMDB00396
NameL-Dihydroorotic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Dihydroorotic acid, also known as (S)-4,5-dihydroorotate or dihydro-L-orotate, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. L-Dihydroorotic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Dihydroorotic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • (S)-2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid
  • (S)-4,5-Dihydroorotate
  • (S)-Dihydroorotate
  • 2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid
  • 4,5-dihydro-L-orotate
  • 5-dihydroorotate
  • Dihydro-L-orotate
  • Dihydro-L-orotic acid
  • L-Dihydroorotate
  • L-Dihydroorotic acid
  • (S)-4,5-Dihydroorotic acid
  • 4,5-Dihydroorotic acid, (L)-isomer
  • 5,6-Dihydroorotate
  • 4,5-Dihydroorotic acid
  • 4,5-Dihydroorotic acid, (DL)-isomer
  • Dihydroorotate
  • Hydroorotic acid
  • 4,5-Dihydroorotic acid, (D)-isomer
CAS number5988-19-2
WeightAverage: 158.1121
Monoisotopic: 158.03275669
InChI KeyUFIVEPVSAGBUSI-REOHCLBHSA-N
InChIInChI=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
IUPAC Name(4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid
Traditional IUPAC NameL-dihydroorotic acid
Chemical FormulaC5H6N2O4
SMILES[H]OC(=O)[C@@]1([H])N([H])C(=O)N([H])C(=O)C1([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • N-acyl urea
  • Pyrimidone
  • Ureide
  • 1,3-diazinane
  • Pyrimidine
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility12.7 g/LALOGPS
logP-1.7ALOGPS
logP-1.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.58 m³·mol⁻¹ChemAxon
Polarizability12.96 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 ReactionsNot Available
KEGG Reactions
Ubiquinone-6 + L-Dihydroorotic acidUbiquinol-6 + Orotic acid
L-Dihydroorotic acid + oxygenOrotic acid + Hydrogen peroxide
water + L-Dihydroorotic acidUreidosuccinic acid + hydron
Fumaric acid + L-Dihydroorotic acidOrotic acid + Succinic acid
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
  • Guyonvarch, A., Nguyen-Juilleret, M., Hubert, J. C., Lacroute, F. (1988). "Structure of the Saccharomyces cerevisiae URA4 gene encoding dihydroorotase." Mol Gen Genet 212:134-141.2897615
  • Nagy, M., Lacroute, F., Thomas, D. (1992). "Divergent evolution of pyrimidine biosynthesis between anaerobic and aerobic yeasts." Proc Natl Acad Sci U S A 89:8966-8970.1409592
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17025
HMDB IDHMDB03349
Pubchem Compound ID439216
Kegg IDC00337
ChemSpider ID388355
FOODB IDFDB023149
Wikipedia4,5-Dihydroorotic_acid
BioCyc IDDI-H-OROTATE

Enzymes

General function:
Involved in dihydroorotase activity
Specific function:
(S)-dihydroorotate + H(2)O = N-carbamoyl-L- aspartate
Gene Name:
URA4
Uniprot ID:
P20051
Molecular weight:
40313.0
Reactions
(S)-dihydroorotate + H(2)O → N-carbamoyl-L-aspartate.
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