Identification

Name
Uracil
Accession Number
DB03419  (EXPT03201)
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
BMS-205603-01 / NSC-3970 / SQ-6201
Categories
UNII
56HH86ZVCT
CAS number
66-22-8
Weight
Average: 112.0868
Monoisotopic: 112.027277382
Chemical Formula
C4H4N2O2
InChI Key
ISAKRJDGNUQOIC-UHFFFAOYSA-N
InChI
InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
IUPAC Name
1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
O=C1NC=CC(=O)N1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydropyrimidine dehydrogenase [NADP(+)]Not AvailableHuman
UUridine-cytidine kinase-like 1Not AvailableHuman
UUracil-DNA glycosylaseNot AvailableHHV-1
UUracil-DNA glycosylaseNot AvailableEscherichia coli O157:H7
URibosomal small subunit pseudouridine synthase ANot AvailableEscherichia coli (strain K12)
UUracil-DNA glycosylaseNot AvailableThermus thermophilus
UPyrimidine-nucleoside phosphorylaseNot AvailableGeobacillus stearothermophilus
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
Carnosinuria, carnosinemiaDisease
Beta-Alanine MetabolismMetabolic
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
GABA-Transaminase DeficiencyDisease
Ureidopropionase DeficiencyDisease
Beta Ureidopropionase DeficiencyDisease
Dihydropyrimidinase DeficiencyDisease
UMP Synthase Deficiency (Orotic Aciduria)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Kurt Klemm, Wolfgang Schoetensack, Wolfgang Prusse, "Aryl-substituted piperazinyl-alkylamino-uracils, -uracil ethers and -uracil thioethers and method for their production." U.S. Patent US3957786, issued September, 1951.

US3957786
General References
Not Available
External Links
Human Metabolome Database
HMDB00300
KEGG Drug
D00027
KEGG Compound
C00106
PubChem Compound
1174
PubChem Substance
46504697
ChemSpider
1141
ChEBI
17568
ChEMBL
CHEMBL566
HET
URA
PDB Entries
1bd4 / 1brw / 1emj / 1flz / 1gth / 1jls / 1ksk / 1ksl / 1oe5 / 1q3f
show 39 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2Unknown StatusPreventionCancer, Breast / Palmar-plantar Erythrodysesthesia (PPE)1
2CompletedTreatmentHepatocellular,Carcinoma2
2CompletedTreatmentMalignant Neoplasm of Stomach1
2CompletedTreatmentMetastatic Colorectal Cancers1
2Unknown StatusTreatmentNeoplasms, Esophageal1
3CompletedTreatmentCancer, Breast2
3CompletedTreatmentColorectal Cancers2
3CompletedTreatmentMalignant Neoplasm of Stomach1
3TerminatedTreatmentM0 / N0-2 / Rectal Carcinoma / Stage II/III / T3 or T4 (Only Anal Extension) Rectal Cancer1

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)338 °CPhysProp
water solubility3600 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.07HANSCH,C ET AL. (1995)
logS-1.48ADME Research, USCD
Caco2 permeability-5.37ADME Research, USCD
pKa9.45MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility26.5 mg/mLALOGPS
logP-1.2ALOGPS
logP-0.86ChemAxon
logS-0.63ALOGPS
pKa (Strongest Acidic)9.77ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.97 m3·mol-1ChemAxon
Polarizability9.37 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9591
Blood Brain Barrier+0.9907
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.785
P-glycoprotein inhibitor INon-inhibitor0.9543
P-glycoprotein inhibitor IINon-inhibitor0.9968
Renal organic cation transporterNon-inhibitor0.9073
CYP450 2C9 substrateNon-substrate0.7561
CYP450 2D6 substrateNon-substrate0.8331
CYP450 3A4 substrateNon-substrate0.793
CYP450 1A2 substrateNon-inhibitor0.7271
CYP450 2C9 inhibitorNon-inhibitor0.9713
CYP450 2D6 inhibitorNon-inhibitor0.9719
CYP450 2C19 inhibitorNon-inhibitor0.981
CYP450 3A4 inhibitorNon-inhibitor0.9707
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.993
Ames testNon AMES toxic0.9178
CarcinogenicityNon-carcinogens0.9471
BiodegradationReady biodegradable0.7648
Rat acute toxicity1.2228 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9614
hERG inhibition (predictor II)Non-inhibitor0.968
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-MSsplash10-0002-5950000000-18425875415ad150c4fc
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-006t-9740000000-e884a4b98e7e9dc75e5f
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-052e-7790000000-026cb6beb5cde6a61b80
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-02tc-9200000000-4a57c4e06fd552d6a9bf
GC-MS Spectrum - EI-BGC-MSsplash10-03xu-9400000000-1c29f070a8135b06f88b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-5950000000-18425875415ad150c4fc
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-006t-9740000000-e884a4b98e7e9dc75e5f
GC-MS Spectrum - GC-MSGC-MSsplash10-052e-7790000000-026cb6beb5cde6a61b80
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-6940000000-a726178341f6443e60cc
Mass Spectrum (Electron Ionization)MSsplash10-03xu-9400000000-d7ffe72f606f1af3349b
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-03di-3900000000-e422eda255a4b6414f86
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-006y-9000000000-130eb5f4414426e03667
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0006-9100000000-c096d08ca715d97cd732
MS/MS Spectrum - EI-B (HITACHI M-60) , PositiveLC-MS/MSsplash10-02tc-9200000000-83a0a6ad4fc1b407e570
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-03xu-9400000000-acd0cfd54af7d6a55283
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-03di-0900000000-309fe212c929f3c6a930
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-03di-6900000000-55a7de75a40eab61da8b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0006-9000000000-1c3caab26eb7e359db92
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-7494d4e611a73ecb79ea
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-ed4046b040337db620d8
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-03di-0900000000-ff54f3083ce4ccccfd95
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-03di-0900000000-6728c1eb6f68b40c09f8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-0029cbdcaa1377a4d03e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0229-9400000000-c227e1deb392170cb323
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-3cf6f9fc3ab6890266ac
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-4900000000-67a3d94ab649e28bda13
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-bbf50de54fc413b6588e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-98042b91f1087b0c2563
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-309fe212c929f3c6a930
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-6900000000-55a7de75a40eab61da8b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-1c3caab26eb7e359db92
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-7494d4e611a73ecb79ea
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-ed4046b040337db620d8
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03di-0900000000-6728c1eb6f68b40c09f8
MS/MS Spectrum - , negativeLC-MS/MSsplash10-03di-0900000000-a21102c708f8d5eaf262
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0900000000-ff54f3083ce4ccccfd95
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C 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 pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Pyrimidones
Alternative Parents
Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides
show 1 more
Substituents
Pyrimidone / Hydropyrimidine / Heteroaromatic compound / Vinylogous amide / Urea / Lactam / Azacycle / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound
show 5 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidone, pyrimidine nucleobase (CHEBI:17568) / pyrimidines (C00106) / a pyrimidine-related compound, a pyrimidine base (URACIL)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine. Also involved the degradation of the chemotherapeutic drug 5-fluorouracil.
Gene Name
DPYD
Uniprot ID
Q12882
Uniprot Name
Dihydropyrimidine dehydrogenase [NADP(+)]
Molecular Weight
111400.32 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
Human
Pharmacological action
Unknown
General Function
Uridine kinase activity
Specific Function
May contribute to UTP accumulation needed for blast transformation and proliferation.
Gene Name
UCKL1
Uniprot ID
Q9NWZ5
Uniprot Name
Uridine-cytidine kinase-like 1
Molecular Weight
61140.395 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
HHV-1
Pharmacological action
Unknown
General Function
Uracil dna n-glycosylase activity
Specific Function
Excises uracil residues from the DNA which can arise as a result of misincorporation of dUMP residues by DNA polymerase or deamination of cytosine. Therefore may reduce deleterious uracil incorpora...
Gene Name
Not Available
Uniprot ID
P10186
Uniprot Name
Uracil-DNA glycosylase
Molecular Weight
36327.865 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 O157:H7
Pharmacological action
Unknown
General Function
Uracil dna n-glycosylase activity
Specific Function
Excises uracil residues from the DNA which can arise as a result of misincorporation of dUMP residues by DNA polymerase or due to deamination of cytosine.
Gene Name
ung
Uniprot ID
Q8X444
Uniprot Name
Uracil-DNA glycosylase
Molecular Weight
25662.02 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
General Function
Rna binding
Specific Function
Responsible for synthesis of pseudouridine from uracil-516 in 16S ribosomal RNA.
Gene Name
rsuA
Uniprot ID
P0AA43
Uniprot Name
Ribosomal small subunit pseudouridine synthase A
Molecular Weight
25865.12 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
Thermus thermophilus
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
udg
Uniprot ID
Q5SKC5
Uniprot Name
Uracil-DNA glycosylase
Molecular Weight
22965.68 Da
Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Pyrimidine-nucleoside phosphorylase activity
Specific Function
Catalyzes phosphorolysis of the pyrimidine nucleosides uridine, thymidine and 2'-deoxyuridine with the formation of the corresponding pyrimidine base and ribose-1-phosphate.
Gene Name
pdp
Uniprot ID
P77836
Uniprot Name
Pyrimidine-nucleoside phosphorylase
Molecular Weight
46331.92 Da

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:27