Identification

Name
Orotic Acid
Accession Number
DB02262  (EXPT02447)
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
61H4T033E5
CAS number
65-86-1
Weight
Average: 156.0963
Monoisotopic: 156.017106626
Chemical Formula
C5H4N2O4
InChI Key
PXQPEWDEAKTCGB-UHFFFAOYSA-N
InChI
InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
IUPAC Name
2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
SMILES
OC(=O)C1=CC(=O)NC(=O)N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydroorotate dehydrogenase A (fumarate)Not AvailableLactococcus lactis subsp. cremoris
UOrotate phosphoribosyltransferaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
UDihydroorotate dehydrogenase (quinone), mitochondrialNot AvailableHuman
UDihydroorotate dehydrogenase (quinone)Not AvailableEscherichia coli (strain K12)
UDihydroorotase
inhibitor
Escherichia 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
Dihydropyrimidinase DeficiencyDisease
beta-Ureidopropionase DeficiencyDisease
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
Pyrimidine MetabolismMetabolic
Pyrimidine MetabolismMetabolic
UMP Synthase Deficiency (Orotic Aciduria)Disease
Pyrimidine Metabolism Metabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Paul Rambacher, Siegfried Make, "Process for preparing orotic acid." U.S. Patent US4062847, issued November, 1960.

US4062847
General References
Not Available
External Links
Human Metabolome Database
HMDB0000226
KEGG Drug
D00055
KEGG Compound
C00295
PubChem Compound
967
PubChem Substance
46508903
ChemSpider
942
ChEBI
16742
ChEMBL
CHEMBL1235017
Therapeutic Targets Database
DNC001065
HET
ORO
PDB Entries
1d3g / 1d3h / 1ep2 / 1f76 / 1j79 / 1jqv / 1jqx / 1jrb / 1jrc / 1lh0
show 85 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2RecruitingPreventionViral sepsis / Viruria1
Not AvailableCompletedDiagnosticSeasonal Allergic Rhinitis (SAR)1

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)345.5 °CPhysProp
water solubility1820 mg/L (at 18 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.83SANGSTER (1994)
logS-1.93ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility4.51 mg/mLALOGPS
logP-0.89ALOGPS
logP-1.2ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.83ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.27 m3·mol-1ChemAxon
Polarizability12.46 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5451
Blood Brain Barrier+0.8092
Caco-2 permeable-0.8368
P-glycoprotein substrateNon-substrate0.7138
P-glycoprotein inhibitor INon-inhibitor0.9897
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9671
CYP450 2C9 substrateNon-substrate0.7072
CYP450 2D6 substrateNon-substrate0.8144
CYP450 3A4 substrateNon-substrate0.7887
CYP450 1A2 substrateNon-inhibitor0.5857
CYP450 2C9 inhibitorNon-inhibitor0.9709
CYP450 2D6 inhibitorNon-inhibitor0.94
CYP450 2C19 inhibitorNon-inhibitor0.9604
CYP450 3A4 inhibitorNon-inhibitor0.9457
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity1.0
Ames testNon AMES toxic0.9385
CarcinogenicityNon-carcinogens0.9437
BiodegradationReady biodegradable0.8393
Rat acute toxicity1.6077 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9864
hERG inhibition (predictor II)Non-inhibitor0.979
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-MSsplash10-0udi-1982000000-b20f2ec9a2f1acc84ae1
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0zfr-2693000000-07bf11b5177412647d9b
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-1982000000-b20f2ec9a2f1acc84ae1
GC-MS Spectrum - GC-MSGC-MSsplash10-0zfr-2693000000-07bf11b5177412647d9b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-1972000000-c04fb7381d3ca07c9b0a
Mass Spectrum (Electron Ionization)MSsplash10-066r-9300000000-e5c3ef3304f93a38628c
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-03di-0900000000-81d73aed73c250fff3ae
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0006-9300000000-ecb08d1854a2789480d1
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0006-9100000000-15748a4c13636c42f4f9
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-02ti-4900000000-6fd6312d81f94faaaf11
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-03di-0900000000-1b7abf52e4a01cb85541
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-0900000000-1ad59feda583f2247b21
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-2900000000-0d0d27215e9f39a2a15b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-918a38777f5d4e049697
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-d7bbee7f2dc7bb0c6a83
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-7900000000-303fe3e06e98f518a2ee
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-b2c02975bbba65c2f1c6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-0900000000-1ad59feda583f2247b21
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-2900000000-0d0d27215e9f39a2a15b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-918a38777f5d4e049697
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-d7bbee7f2dc7bb0c6a83
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-7900000000-303fe3e06e98f518a2ee
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-b2c02975bbba65c2f1c6
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03di-0900000000-1b7abf52e4a01cb85541
MS/MS Spectrum - , negativeLC-MS/MSsplash10-03di-0900000000-3dff3caa5c10aff8ce46
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-02ti-4900000000-6fd6312d81f94faaaf11
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyrimidinecarboxylic acids. These are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Pyrimidinecarboxylic acids
Alternative Parents
Hydropyrimidine carboxylic acids and derivatives / Pyrimidones / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Hydropyrimidine carboxylic acid derivative / Pyrimidine-6-carboxylic acid / Pyrimidone / Hydropyrimidine / Vinylogous amide / Heteroaromatic compound / Lactam / Urea / Carboxylic acid derivative / Monocarboxylic acid or derivatives
show 10 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidinemonocarboxylic acid (CHEBI:16742)

Targets

Kind
Protein
Organism
Lactococcus lactis subsp. cremoris
Pharmacological action
Unknown
General Function
Dihydroorotate dehydrogenase (fumarate) activity
Specific Function
Catalyzes the conversion of dihydroorotate to orotate with fumarate as the electron acceptor.
Gene Name
pyrDA
Uniprot ID
Q53ZE5
Uniprot Name
Dihydroorotate dehydrogenase A (fumarate)
Molecular Weight
34209.99 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]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Orotate phosphoribosyltransferase activity
Specific Function
Catalyzes the transfer of a ribosyl phosphate group from 5-phosphoribose 1-diphosphate to orotate, leading to the formation of orotidine monophosphate (OMP).
Gene Name
pyrE
Uniprot ID
P08870
Uniprot Name
Orotate phosphoribosyltransferase
Molecular Weight
23561.74 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquinone binding
Specific Function
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name
DHODH
Uniprot ID
Q02127
Uniprot Name
Dihydroorotate dehydrogenase (quinone), mitochondrial
Molecular Weight
42866.93 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Fmn binding
Specific Function
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name
pyrD
Uniprot ID
P0A7E1
Uniprot Name
Dihydroorotate dehydrogenase (quinone)
Molecular Weight
36774.185 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]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
Actions
Inhibitor
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]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:14