Thiouracil (CHEM016042)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:12:14 UTC
Update Date2016-11-09 01:15:19 UTC
Accession NumberCHEM016042
Identification
Common NameThiouracil
ClassSmall Molecule
DescriptionA nucleobase analogue that is uracil in which the oxo group at C-2 is replaced by a thioxo group.
Contaminant Sources
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Mercapto-4-pyrimidinolChEBI
2-Mercapto-pyrimidin-4-olChEBI
2-Thio-2,4-(1H,3H)-pyrimidinedioneChEBI
2-Thioxo-2,3-dihydro-1H-pyrimidin-4-oneChEBI
4-Hydroxy-2-pyrimidinethiolChEBI
2-ThiouracilChEBI
Chemical FormulaC4H4N2OS
Average Molecular Mass128.150 g/mol
Monoisotopic Mass128.004 g/mol
CAS Registry Number141-90-2
IUPAC Name2-sulfanylpyrimidin-4-ol
Traditional Namethiouracil
SMILESO=C1NC(=S)NC=C1
InChI IdentifierInChI=1S/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
InChI KeyZEMGGZBWXRYJHK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidones. Pyrimidones 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • 2-thiopyrimidine
  • Pyrimidinethione
  • Thiopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Thiourea
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.07 g/LALOGPS
logP0.66ALOGPS
logP1.11ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.59ChemAxon
pKa (Strongest Basic)-0.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.01 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.97 m³·mol⁻¹ChemAxon
Polarizability11.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9500000000-eab1e76e208a04d8b7fdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a4i-9000000000-acdbd4788bf0a434a52cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-9100000000-cf0c5c9572f71b6eba5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0a4i-9000000000-e858eafc5134f3cf550eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a4i-9000000000-a9c898b892745c0b70b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a4i-9100000000-0b1ce3785921376f2043Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-9f8f024f81f98f1dacd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0200-5900000000-bfe6b77986d2dc386f6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9100000000-dd5f9ddda2ca38e60d99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-1567016105ab4feedccaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-5eafaa36245c36c5843aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-224f2c04cb80f9342880Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-2252c6ccc6fb51a35767Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-eb3c19358cb565f649a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktf-9000000000-9cd8b260d0485d9775e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-6900000000-bb457639aeb6adf3e6e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-5b76794ce1539b20b552Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-4de757fe428d108bdf7dSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0245323
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkThiouracil
Chemspider ID1066108
ChEBI ID348530
PubChem Compound ID1586
Kegg Compound IDC19304
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11094150
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23739752
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23740976
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=3654008
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=4316226
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=7120285
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=8068712
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=8978847
9. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.