Thiourea
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Basic Info
| Common Name | Thiourea(F05587) |
| 2D Structure | |
| Description | Thiourea 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 (A7927, A7928, A7929). |
| FRCD ID | F05587 |
| CAS Number | 62-56-6 |
| PubChem CID | 2723790 |
| Formula | CH4N2S |
| IUPAC Name | thiourea |
| InChI Key | UMGDCJDMYOKAJW-UHFFFAOYSA-N |
| InChI | InChI=1S/CH4N2S/c2-1(3)4/h(H4,2,3,4) |
| Canonical SMILES | C(=S)(N)N |
| Isomeric SMILES | C(=S)(N)N |
| Wikipedia | Thiourea |
| Synonyms |
2-Thiopseudourea
THIOUREA
Thiocarbamide
62-56-6
2-Thiourea
Pseudothiourea
Isothiourea
Sulourea
Sulfourea
Thiuronium
|
| Classifies |
Predicted: Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organosulfur compounds |
| Class | Thioureas |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Thioureas |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Thiourea - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aliphatic acyclic compound |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 76.117 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 29 |
| Monoisotopic Mass | 76.01 |
| Exact Mass | 76.01 |
| XLogP | -0.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 4 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8912 |
| Human Intestinal Absorption | HIA+ | 0.8750 |
| Caco-2 Permeability | Caco2- | 0.6739 |
| P-glycoprotein Substrate | Non-substrate | 0.8850 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9659 |
| Non-inhibitor | 0.9911 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9208 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.7130 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8293 |
| CYP450 2D6 Substrate | Non-substrate | 0.7747 |
| CYP450 3A4 Substrate | Non-substrate | 0.8692 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7773 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7438 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9696 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8765 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9049 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8547 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9793 |
| Non-inhibitor | 0.9680 | |
| AMES Toxicity | Non AMES toxic | 0.9708 |
| Carcinogens | Non-carcinogens | 0.7402 |
| Fish Toxicity | High FHMT | 0.6397 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6988 |
| Honey Bee Toxicity | High HBT | 0.6980 |
| Biodegradation | Not ready biodegradable | 0.7962 |
| Acute Oral Toxicity | II | 0.7109 |
| Carcinogenicity (Three-class) | Non-required | 0.5253 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.2573 | LogS |
| Caco-2 Permeability | 0.8903 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.1168 | LD50, mol/kg |
| Fish Toxicity | 2.4468 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3966 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Effect of Diafenthiuron exposure under short and long term experimentalconditions on hematology, serum biochemical profile and elemental composition of a non-target organism, Labeo rohita. | Environ Toxicol Pharmacol | 2018 Sep | 29957367 |
| Magnetic mesoporous thiourea-formaldehyde resin as selective adsorbent: A simple and highly-sensitive electroanalysis strategy for lead ions in drinking water andmilk by solid state-based anodic stripping. | Food Chem | 2018 Jan 15 | 28873584 |
| Antioxidant, anti-inflammatory, and enzyme inhibitory activity of natural plant flavonoids and their synthesized derivatives. | J Biochem Mol Toxicol | 2018 Jan | 28972678 |
| Determination of inorganic arsenic in algae using bromine halogenation and on-line nonpolar solid phase extraction followed by hydride generation atomic fluorescence spectrometry. | Talanta | 2017 Aug 1 | 28501152 |
| Bactericidal activity of alpha-bromocinnamaldehyde against persisters in Escherichia coli. | PLoS One | 2017 | 28750057 |
| Asymmetric Synthesis and Bioselective Activities of α-Amino-phosphonates Based onthe Dufulin Motif. | J Agric Food Chem | 2016 Jun 1 | 27166879 |
| Sulfur crosslinks from thermal degradation of chitosan dithiocarbamatederivatives and thermodynamic study for sorption of copper and cadmium fromaqueous system. | Environ Sci Pollut Res Int | 2016 Jan | 26538256 |
| Biosorption using chitosan thiourea polymer as an extraction and preconcentrationtechnique for copper prior to its determination in environmental and food samplesby flame atomic absorption spectrometry: Synthesis, characterization andanalytical applications. | Int J Biol Macromol | 2016 Dec | 27565297 |
| Adsorptive removal of patulin from aqueous solution using thiourea modified chitosan resin. | Int J Biol Macromol | 2015 Sep | 26188299 |
| Synthesis of an imprinted polymer for the determination of methylmercury inmarine products. | Talanta | 2015 Nov 1 | 26452871 |
| Application of "hydrogen bonding interaction" in new drug development: design,synthesis, antiviral activity, and SARs of thiourea derivatives. | J Agric Food Chem | 2015 Feb 11 | 25619875 |
| Characterization of a flavin-containing monooxygenase from Corynebacteriumglutamicum and its application to production of indigo and indirubin. | Biotechnol Lett | 2015 Aug | 25851950 |
| Efficient generation of volatile species for cadmium analysis in seafood and ricesamples by a modified chemical vapor generation system coupled with atomicfluorescence spectrometry. | Anal Chim Acta | 2015 Apr 15 | 25818135 |
| Synthesis and characterization of a novel mesoporous silica functionalized with[1,5 bis(di-2-pyridyl)methylene thiocarbohydrazide] and its application asenrichment sorbent for determination of antimony by FI-HG-ETAAS. | Talanta | 2014 Nov | 25127557 |
| Solid phase extraction of trace amounts of silver, cadmium, copper, mercury, and lead in various food samples based on ethylene glycol bis-mercaptoacetatemodified 3-(trimethoxysilyl)-1-propanethiol coated Fe3O4 nanoparticles. | Food Chem | 2014 May 15 | 24423536 |
| In vitro inhibition effect and structure-activity relationships of some saccharinderivatives on erythrocyte carbonic anhydrase I and II. | J Enzyme Inhib Med Chem | 2014 Feb | 23339426 |
| Differential mechanism of Escherichia coli Inactivation by (+)-limonene as afunction of cell physiological state and drug's concentration. | PLoS One | 2014 Apr 4 | 24705541 |
| Thiourea, a ROS scavenger, regulates source-to-sink relationship to enhance crop yield and oil content in Brassica juncea (L.). | PLoS One | 2013 Sep 18 | 24058504 |
| Rapid detection of economic adulterants in fresh milk by liquidchromatography-tandem mass spectrometry. | J Chromatogr A | 2013 May 3 | 23540766 |
| Human taste receptor-functionalized field effect transistor as a human-like nanobioelectronic tongue. | Nano Lett | 2013 Jan 9 | 23176205 |
Targets
- 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
References
- 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 ]