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Thiourea (T3D4891)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-09-11 05:21:05 UTC
Update Date2014-12-24 20:26:59 UTC
Accession NumberT3D4891
Identification
Common NameThiourea
ClassSmall Molecule
DescriptionThiourea is an organic compound of carbon, nitrogen, sulfur and hydrogen, with the formula CSN2H4 or (NH2)2CS. It is similar to urea, except that the oxygen atom is replaced by a sulfur atom. The properties of urea and thiourea differ significantly because of the relative electronegativities of sulfur and oxygen. Thiourea is a versatile reagent in organic synthesis. "Thioureas" refers to a broad class of compounds with the general structure (R1R2N)(R3R4N)C=S. Thioureas are related to thioamides, e.g. RC(S)NR2, where R is methyl, ethyl, etc. Thiourea is prohibited from use in food. Industrial uses of thiourea include production of flame retardant resins, and vulcanization accelerators. Thiourea is used as an auxiliary agent in diazo paper (light-sensitive photocopy paper) and almost all other types of copy paper. It is also used to tone silver-gelatin photographic prints. The liquid silver cleaning product TarnX is essentially a solution of thiourea. A leaching agent for gold leaching and silver leaching can be created by selectively oxidizing thiourea, bypassing the steps of cyanide use and smelting. Another common application for use of thiourea is a common sulfur source for making semiconductor cadmium sulfide nanoparticle. Thiourea is a planar molecule. The C=S bond distance is 1.60±0.1 for a wide range of derivatives. This narrow range indicates that the C=S bond is insensitive to the nature of the substitutent. Thus, the thioamide, which is similar to an amide group, is difficult to perturb. Thiourea reduces peroxides to the corresponding diols. The intermediate of the reaction is an unstable epidioxide which can only be identified at -100 °C. Epidioxide is similar to epoxide except with two oxygen atoms. This intermediate reduces to diol by thiourea. Thiourea has been shown to exhibit anti-viral, anti-fungal and radical scavenger functions (1, 2, 3).
Compound Type
  • Amine
  • Food Toxin
  • Household Toxin
  • Indicator and Reagent
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(NH2)2CS
2-Thio-Pseudourea
2-Thio-Urea
2-Thiopseudourea
2-Thiourea
beta -thiopseudourea
beta-Thiopseudourea
Carbonothioic diamide
H2NC(S)NH2
Isothiourea
Pseudothiourea
Sulfocarbamide
Sulfourea
Sulfouren
Sulourea
Thio-Urea
Thiocarbamid
Thiocarbamide
Thiocarbonic acid diamide
Thiocarbonic diamide
Thioharnstoff
Thiokarbamid
Thiomocovina
Thiourea, acs
Thiurea
Thiuronium
THU
TOU
Tsizp 34
TU
Urea, thio- (8CI)
Chemical FormulaCH4N2S
Average Molecular Mass76.121 g/mol
Monoisotopic Mass76.010 g/mol
CAS Registry Number62-56-6
IUPAC Namethiourea
Traditional Namethiourea
SMILESNC(S)=N
InChI IdentifierInChI=1S/CH4N2S/c2-1(3)4/h(H4,2,3,4)
InChI KeyInChIKey=UMGDCJDMYOKAJW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thioureas. These are organic compounds containing the thiourea functional group, a derivative of urea with the general structure (R1(N)R2C(=S)(R3)R4, R1-R4=H, alkyl, aryl), obtained by replacing the carbonyl group of urea with a thiocarbonyl group.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThioureas
Sub ClassNot Available
Direct ParentThioureas
Alternative Parents
Substituents
  • Thiourea
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point180 °C
Boiling PointDecomposes. None
Solubility142 mg/mL at 25 °C
LogP-1.08
Predicted Properties
PropertyValueSource
Water Solubility21.2 g/LALOGPS
logP-1.1ALOGPS
logP-0.47ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)13.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.13 m³·mol⁻¹ChemAxon
Polarizability7.14 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-8e5bcf535608a9c5c7952017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-fc85c4c4965deff19a4b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-9df13a5f6817f41fe8cf2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-5e86038161f25d0f48202021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-006549670e02390c97cb2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-6c868e007f78c8b9e10e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-837112ddd5e6429124e72021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-63a30c532af48a8e12b12016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-1447f942ca93d2d6a2c72016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-c202fd1bcbae71404d362016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-9000000000-47b3f247781166d2b51a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9000000000-f31b460d9dd139df11da2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-6c446727638b12dd42622016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6u-9000000000-ca5a647850195cd117e72021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-9000000000-41ef030e882c2237b1422021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-921fd3a13e7c6371da152021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-921fd3a13e7c6371da152021-09-24View Spectrum
MSMass Spectrum (Electron Ionization)splash10-004l-9000000000-266e84d73e39423453202014-09-20View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (5)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB34155
PubChem Compound ID2723790
ChEMBL IDCHEMBL260876
ChemSpider ID2005981
KEGG IDC14415
UniProt IDNot Available
OMIM ID
ChEBI ID36946
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDTOU
ACToR IDNot Available
Wikipedia LinkThiourea
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Chen MH, Chen Z, Song BA, Bhadury PS, Yang S, Cai XJ, Hu DY, Xue W, Zeng S: Synthesis and antiviral activities of chiral thiourea derivatives containing an alpha-aminophosphonate moiety. J Agric Food Chem. 2009 Feb 25;57(4):1383-8. doi: 10.1021/jf803215t. [19199594 ]
  2. Shankar V, Pandeya SN: Synthesis of a series of new N1-[4-(4-nitrophenylthio)phenyl]-N3-(H/alkyl/acyl/aryl) thioureas and their antifungal, insecticidal and larvicidal activities. Arzneimittelforschung. 1981;31(5):753-6. [7196731 ]
  3. Vogelpoel FR, van Kooij RJ, te Velde ER, Verhoef J: Influence of polymorphonuclear granulocytes on the zona-free hamster oocyte assay. Hum Reprod. 1991 Sep;6(8):1104-7. [1806570 ]
  4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Estrogen receptor
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.81 uMACEA_T47D_80hr_PositiveACEA Biosciences
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]