4,5-Dihydroorotic acid (ECMDB00528) (M2MDB000147)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (1083)
Record Information
Version2.0
Creation Date2012-05-31 10:27:15 -0600
Update Date2015-06-03 15:53:30 -0600
Secondary Accession Numbers
  • ECMDB00528
Identification
Name:4,5-Dihydroorotic acid
Description4,5-Dihydroorotic acid is a substrate of the enzyme orotate reductase [EC 1.3.1.14], which is part of the pyrimidine metabolism pathway. (KEGG) Dihydroorotate is oxidized by Dihydroorotate dehydrogenases (DHODs) to orotate. These dehydrogenases use their FMN (flavin mononucleotide) prosthetic group to abstract a hydride equivalent from C6 to deprotonate C5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
  • (+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
  • (S)-4,5-dihydroorotate
  • (S)-4,5-dihydroorotic acid
  • (S)-4-pyrimidinecarboxylic acid
  • (S)-di-H-orotate
  • (S)-hydroorotic acid
  • (R)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
  • (R)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
  • (S)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
  • (S)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
  • (S)-4,5-Dihydroorotate
  • (S)-4,5-dihydroorotic acid
  • (S)-4-pyrimidinecarboxylate
  • (S)-4-pyrimidinecarboxylic acid
  • (S)-di-H-orotate
  • (S)-di-H-orotic acid
  • (S)-Dihydroorotate
  • (S)-Dihydroorotic acid
  • (S)-hydroorotate
  • (S)-hydroorotic acid
  • 2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
  • 2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
  • 4,5-Dihydro-L-orotate
  • 4,5-Dihydro-L-orotic acid
  • 4,5-Dihydroorotate
  • 4,5-Dihydroorotic acid
  • 5,6-Dihydroorotate
  • 5,6-Dihydroorotic acid
  • Dihydro-L-orotate
  • Dihydro-L-orotic acid
  • L-4,5-Dihydroorotate
  • L-4,5-Dihydroorotic acid
  • L-Dihydroorotate
  • L-Dihydroorotic acid
  • L-Hydroorotate
  • L-Hydroorotic acid
  • R,S-Hydroorotate
  • R,S-Hydroorotic acid
Chemical Formula:C5H6N2O4
Weight:Average: 158.1121
Monoisotopic: 158.03275669
InChI Key:UFIVEPVSAGBUSI-UHFFFAOYSA-N
InChI: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)
CAS number:155-54-4
IUPAC Name:2,6-dioxo-1,3-diazinane-4-carboxylic acid
Traditional IUPAC Name:dihydroorotic acid
SMILES:OC(=O)C1CC(=O)NC(=O)N1
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
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Polarizability13.09 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
4,5-Dihydroorotic acid + Ubiquinone-8 > Orotic acid + Ubiquinol-8
4,5-Dihydroorotic acid + Menaquinone 8 > Menaquinol 8 + Orotic acid
4,5-Dihydroorotic acid + Water <> Ureidosuccinic acid + Hydrogen ion
4,5-Dihydroorotic acid + Fumaric acid <> Orotic acid + Succinic acid
4,5-Dihydroorotic acid + Water <> Ureidosuccinic acid
4,5-Dihydroorotic acid + a ubiquinone > Orotic acid + a ubiquinol
4,5-Dihydroorotic acid + a menaquinone > Orotic acid + a menaquinol
4,5-Dihydroorotic acid + Quinone <> Orotic acid + Hydroquinone
N-carbamoyl-L-aspartate + Hydrogen ion > Water + 4,5-Dihydroorotic acid + 4,5-Dihydroorotic acid
4,5-Dihydroorotic acid + Ubiquinone-1 + 4,5-Dihydroorotic acid > Ubiquinol-1 + Orotic acid
4 4,5-Dihydroorotic acid + Fumaric acid <> Orotic acid + Succinic acid
4 4,5-Dihydroorotic acid + Quinone <> Orotic acid + Hydroquinone
4 4,5-Dihydroorotic acid + Water <> Ureidosuccinic acid + Hydrogen ion
4 4,5-Dihydroorotic acid + Fumaric acid <> Orotic acid + Succinic acid
SMPDB Pathways:
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
12± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
5± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
4± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9400000000-248b8d6d703ba73c2058View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-3900000000-b0776f22820e6e570a09View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-059i-9700000000-c8ce0433c02db41880b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-56601203ef19b09212feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9000000000-b6342346ce51dd871eaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2ddb498acc970a567f6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-5900000000-4b73ae512e57466dd4e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-d6c31a36d6fe5c68d9e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-c84801951eaa1da750f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-4ae1d11ab20f903606c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-aec3a40befb20e60f21bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06r6-0900000000-86736ae769db7bc83c23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5900000000-f6e9e0cbdc2adf67aa89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-aac58a007ab745825d74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-b0c5e687f246809cdae9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-6900000000-cb60b796898e6ca4336dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-fccf5d7216b23cffed7aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
Synthesis Reference:Burger, Klaus; Neuhauser, Horst; Rudolph, Martin. A new, preparatively simple way to dihydroorotic acid, 1-methyl-4,5-dihydroorotic acid and their derivatives. Chemiker-Zeitung (1990), 114(7-8), 251-5.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID30865
HMDB IDHMDB00528
Pubchem Compound ID648
Kegg IDC00337
ChemSpider ID628
Wikipedia4,5-Dihydroorotic acid
BioCyc IDDI-H-OROTATE
EcoCyc IDDI-H-OROTATE

Enzymes

Protein Details
1. Dihydroorotase
General function:
Involved in hydrolase activity
Specific function:
(S)-dihydroorotate + H(2)O = N-carbamoyl-L- aspartate
Gene Name:
pyrC
Uniprot ID:
P05020
Molecular weight:
38827
Reactions
(S)-dihydroorotate + H(2)O = N-carbamoyl-L-aspartate.
Protein Details
2. Dihydroorotate dehydrogenase
General function:
Involved in catalytic activity
Specific function:
(S)-dihydroorotate + a quinone = orotate + a quinol
Gene Name:
pyrD
Uniprot ID:
P0A7E1
Molecular weight:
36774
Reactions
(S)-dihydroorotate + a quinone = orotate + a quinol.