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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:46 UTC
HMDB IDHMDB00528
Secondary Accession Numbers
  • HMDB11746
Metabolite Identification
Common Name4,5-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
Synonyms
  1. (+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
  2. (+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
  3. (R)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
  4. (R)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
  5. (S)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
  6. (S)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
  7. 2,6-Dioxo-hexahydro-pyrimidine-4-carboxylate
  8. 2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acid
  9. 4,5-Dihydroorotate
  10. 4,5-Dihydroorotic acid
  11. 5,6-Dihydroorotate
  12. L-Hydroorotate
  13. L-Hydroorotic acid
  14. R,S-Hydroorotate
Chemical FormulaC5H6N2O4
Average Molecular Weight158.1121
Monoisotopic Molecular Weight158.03275669
IUPAC Name2,6-dioxo-1,3-diazinane-4-carboxylic acid
Traditional Namedihydroorotic acid
CAS Registry Number155-54-4
SMILES
OC(=O)C1CC(=O)NC(=O)N1
InChI Identifier
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)
InChI KeyUFIVEPVSAGBUSI-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Heteromonocyclic Compounds
ClassDiazines
Sub ClassPyrimidines and Pyrimidine Derivatives
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Pyrimidines and Pyrimidine Derivatives
  • Ureides
  • dihydroorotic acid(ChEBI)
Substituents
  • Carboxamide Group
  • Carboxylic Acid
  • Carboxylic Acid Imide, N Unsubstituted
  • Urea
Direct ParentPyrimidones
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.7ALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.58 m3·mol-1ChemAxon
Polarizability13.05 Å3ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022096
KNApSAcK IDNot Available
Chemspider ID628
KEGG Compound IDC00337
BioCyc IDDI-H-OROTATE
BiGG IDNot Available
Wikipedia Link4,5-Dihydroorotic acid
NuGOwiki LinkHMDB00528
Metagene LinkHMDB00528
METLIN ID5513
PubChem Compound648
PDB IDNot Available
ChEBI ID30865
References
Synthesis ReferenceBurger, 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
General References
  1. 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

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name:
DHODH
Uniprot ID:
Q02127
Molecular weight:
42866.93
General function:
Involved in hydrolase activity
Specific function:
This protein is a "fusion" protein encoding four enzymatic activities of the pyrimidine pathway (GATase, CPSase, ATCase and DHOase).
Gene Name:
CAD
Uniprot ID:
P27708
Molecular weight:
242981.73