Dihydroorotic Acid

Identification

Generic Name
Dihydroorotic Acid
DrugBank Accession Number
DB02129
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 158.1121
Monoisotopic: 158.03275669
Chemical Formula
C5H6N2O4
Synonyms
Not Available

Pharmacology

Indication

Not Available

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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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Pyrimidine MetabolismMetabolic
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
beta-Ureidopropionase DeficiencyDisease
Dihydropyrimidinase DeficiencyDisease
UMP Synthase Deficiency (Orotic Aciduria)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
1,3-diazinane / Aliphatic heteromonocyclic compound / Alpha-amino acid or derivatives / Azacycle / Carbonic acid derivative / Carbonyl group / Carboxylic acid / Dicarboximide / Hydrocarbon derivative / Monocarboxylic acid or derivatives
show 12 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
dihydroorotic acid (CHEBI:17025)
Affected organisms
Not Available

Chemical Identifiers

UNII
4LPL64ZNA5
CAS number
155-54-4
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

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
Human Metabolome Database
HMDB0003349
KEGG Compound
C00337
PubChem Compound
439216
PubChem Substance
46508825
ChemSpider
388355
ChEBI
17025
ZINC
ZINC000003869850
Therapeutic Targets Database
DNC000559
PDBe Ligand
DOR
PDB Entries
1xge / 2e68 / 2z24 / 2z25 / 2z26 / 2z27 / 2z28 / 2z29 / 2z2a / 3kvj
show 24 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability12.96 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-MSsplash10-000f-9400000000-248b8d6d703ba73c2058
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
MS/MS Spectrum - , negativeLC-MS/MSsplash10-001i-2920000000-1c8b06ed77517a0e8606
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03k9-4900000000-5b6e94f06ce0c97ad751
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-0900000000-b25143f4e6ffdcf9f858
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-1900000000-9f1a2b21de36708e6185
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01bc-5900000000-4346058c963d7c21d579
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-9300000000-602da3008f097947f7a4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-0cc8352e4433db83f6f8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-9000000000-f07abd6bb779f646466d
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
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-132.530664
predicted
DarkChem Lite v0.1.0
[M-H]-132.604564
predicted
DarkChem Lite v0.1.0
[M-H]-132.471664
predicted
DarkChem Lite v0.1.0
[M-H]-125.917984
predicted
DeepCCS 1.0 (2019)
[M+H]+133.525264
predicted
DarkChem Lite v0.1.0
[M+H]+133.427964
predicted
DarkChem Lite v0.1.0
[M+H]+133.495764
predicted
DarkChem Lite v0.1.0
[M+H]+128.50063
predicted
DeepCCS 1.0 (2019)
[M+Na]+133.694064
predicted
DarkChem Lite v0.1.0
[M+Na]+133.512264
predicted
DarkChem Lite v0.1.0
[M+Na]+133.725364
predicted
DarkChem Lite v0.1.0
[M+Na]+137.00005
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52