Dihydroorotic Acid

Identification

Name
Dihydroorotic Acid
Accession Number
DB02129  (EXPT01249)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
4LPL64ZNA5
CAS number
155-54-4
Weight
Average: 158.1121
Monoisotopic: 158.03275669
Chemical Formula
C5H6N2O4
InChI Key
UFIVEPVSAGBUSI-REOHCLBHSA-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)/t2-/m0/s1
IUPAC Name
(4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid
SMILES
OC(=O)[C@@H]1CC(=O)NC(=O)N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydroorotaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Pyrimidine MetabolismMetabolic
Pyrimidine MetabolismMetabolic
UMP Synthase Deficiency (Orotic Aciduria)Disease
Dihydropyrimidinase DeficiencyDisease
beta-Ureidopropionase DeficiencyDisease
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Hiroshi Sugano, Ryuichi Ishida, Michio Yamamura, "Dihydroorotic acid derivative and processes for preparing the same." U.S. Patent US4665056, issued April, 1981.

US4665056
General References
Not Available
External Links
Human Metabolome Database
HMDB0003349
KEGG Compound
C00337
PubChem Compound
439216
PubChem Substance
46508825
ChemSpider
388355
ChEBI
17025
Therapeutic Targets Database
DNC000559
HET
DOR
PDB Entries
1xge / 2e68 / 2z24 / 2z25 / 2z26 / 2z27 / 2z28 / 2z29 / 2z2a / 3kvj
show 20 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.7 mg/mLALOGPS
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
Polarizability13.02 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.817
Blood Brain Barrier+0.6421
Caco-2 permeable-0.7705
P-glycoprotein substrateNon-substrate0.6016
P-glycoprotein inhibitor INon-inhibitor0.9661
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.956
CYP450 2C9 substrateNon-substrate0.7349
CYP450 2D6 substrateNon-substrate0.8267
CYP450 3A4 substrateNon-substrate0.7218
CYP450 1A2 substrateNon-inhibitor0.91
CYP450 2C9 inhibitorNon-inhibitor0.9748
CYP450 2D6 inhibitorNon-inhibitor0.9461
CYP450 2C19 inhibitorNon-inhibitor0.9678
CYP450 3A4 inhibitorNon-inhibitor0.9799
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity1.0
Ames testNon AMES toxic0.8824
CarcinogenicityNon-carcinogens0.9622
BiodegradationReady biodegradable0.907
Rat acute toxicity1.8022 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9913
hERG inhibition (predictor II)Non-inhibitor0.9846
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0zfs-1920000000-6e853bcb65fafce1f25e
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000j-1900000000-4c364adc386eb5db027b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0zfs-0930000000-373786ac89c19f0cbc6b
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0pb9-2951000000-9975cf569acb6854865d
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-005a-5938000000-6f622577780cd53385eb
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0zfs-1920000000-6e853bcb65fafce1f25e
GC-MS Spectrum - GC-MSGC-MSsplash10-0pb9-2951000000-9975cf569acb6854865d
GC-MS Spectrum - GC-MSGC-MSsplash10-005a-5938000000-6f622577780cd53385eb
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-059i-9700000000-681989bb70419ccf0e26
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00di-9000000000-c08746cfe4c476aff942
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-006x-9000000000-c59db6f9b23380c30e8c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , negativeLC-MS/MSsplash10-001i-2920000000-1c8b06ed77517a0e8606
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03k9-4900000000-5b6e94f06ce0c97ad751
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Pyrimidones / N-acyl ureas / Diazinanes / Dicarboximides / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
Alpha-amino acid or derivatives / N-acyl urea / Pyrimidone / Ureide / 1,3-diazinane / Pyrimidine / Dicarboximide / Urea / Carbonic acid derivative / Azacycle
show 12 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
dihydroorotic acid (CHEBI:17025)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
pyrC
Uniprot ID
P05020
Uniprot Name
Dihydroorotase
Molecular Weight
38827.045 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:12