Record Information
Version2.0
Creation Date2014-09-11 05:19:30 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4857
Identification
Common Name2(3H)-Benzothiazolethione
ClassSmall Molecule
Description2(3H)-Benzothiazolethione is found in fruits. 2(3H)-Benzothiazolethione is a constituent of cranberries. 2(3H)-Benzothiazolethione belongs to the family of Benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-member ring with four carbon atoms, one nitrogen atom and one sulfur atom).
Compound Type
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
1,3-Benzothiazol-2-yl hydrosulfide
1,3-Benzothiazole-2-thiol
155-04-4 (Zinc salt)
2(3h)-Benzothiazolethione, Potassium Salt
2-Benzothiazolethiol
2-Benzothiazolethione
2-Benzothiazolinethione
2-Benzothiazolyl mercaptan
2-MBT
2-Mercapto-Benzothiazole
2-Mercaptobenzothiazole
2-Mercaptobenzothiazole (2-MBT)
2-Mercaptobenzothiazole (in liquid mixtures)
2-Mercaptobenzthiazole
2-Mercptobenzothiazole
2-Merkaptobenzotiazol
2-Merkaptobenzthiazol
2-Thiobenzothiazole
4162-43-0 (Copper(+2) salt)
7778-70-3 (Potassium salt)
Accel M
Accelerator M
Accelerator mercapto
Benzothiazole-2-thiol
Benzothiazole-2-thione
Benzothiazolethiol
Captax
Captax, bismuth(+3) salt
Captax, cobalt(+2) salt
Captax, copper(+2) salt
Captax, lead(+2) salt
Captax, mercury (+2) salt
Captax, potassium salt
Captax, silver(+1) salt
Captax, sodium salt
Captax, zinc salt
Dermacid
Drmacid
Ekagom g
Kaptaks
Kaptax
MBT, captax
Mebetizol
Mebetizole
Mebithizol
Mercapto-Benzothiazole
Mercaptobenzothiazol
Mercaptobenzothiazole
Mercaptobenzthiazole
Mertax
Nocceler m
Nuodeb 84
Nuodex 84
Pennac MBT
Pennac MBT powder
Perkacit MBT
Pneumax MBT
Rokon
Rotax
Royal MBT
Soxinol m
Sulfadene
Thiot ax
Thiotax
Vulkacit m
Vulkacit m, vulkacit merkapto/c
Vulkacit mercapto
Vulkacit mercapto/c
Chemical FormulaC7H5NS2
Average Molecular Mass167.251 g/mol
Monoisotopic Mass166.986 g/mol
CAS Registry Number149-30-4
IUPAC Name2,3-dihydro-1,3-benzothiazole-2-thione
Traditional Name2(3H)-benzothiazolethione
SMILESSC1=NC2=CC=CC=C2S1
InChI IdentifierInChI=1S/C7H5NS2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
InChI KeyInChIKey=YXIWHUQXZSMYRE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazoles
Sub ClassNot Available
Direct ParentBenzothiazoles
Alternative Parents
Substituents
  • 1,3-benzothiazole
  • Benzenoid
  • Heteroaromatic compound
  • Thiazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 Point177 - 179 °C
Boiling PointNot Available
Solubility0.12 mg/mL at 24 °C
LogP2.42
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.26ALOGPS
logP2.88ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)10.9ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.7 m³·mol⁻¹ChemAxon
Polarizability16.89 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-014i-1900000000-4d37a61d9cd8301a62d42017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-d4138dd53c1e889f74722017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-5ee2ab0aad359223be6b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-902e833dd3cfb0b485b82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0159-1900000000-fdf61c661e3992d0da852017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-05o0-3900000000-21acddd80ea821c4bf142017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a59-8900000000-6da3258b33992f29c78c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-9100000000-5be3cc8a800a6a145d242017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-9000000000-dbb81dad2d0342550c702017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-9000000000-2e115fed4acdabfa32342017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-671d8a90e7541628f6ef2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-2dfe8d8f0467dabe84e82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-e8e5e62a5f0c06e023052017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-3ea865dce717e700b6752017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-12367cc6bfe2d78f6b892017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-9fafd8a0ed71806552842017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00kr-1900000000-70d04c4c5fa82c7381252017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-2900000000-58ddee392d1b19076ce02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05n0-9800000000-f9f390220b974d6fe5dd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066r-9300000000-8b24e85baac451e5db6f2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0900000000-144cc4642f635cb7caa12016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-104eed79a3d681c970642016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-8918e200add4938f2b7f2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-f0796ea4a78109f4545a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2900000000-672bbede5a3d7a91535c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-f00b14e4ed021b9e3ca22016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-6900000000-10352654a25e614d7e3d2014-09-20View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
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 IDHMDB30524
PubChem Compound ID21831736
ChEMBL IDNot Available
ChemSpider ID13802256
KEGG IDC14437
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4857.pdf
General References
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  5. Tomc C, Kwasniak L, Shoureshi P, Nedorost S: Allergic contact dermatitis probably caused by mercaptobenzothiazole in thermal undergarments. Contact Dermatitis. 2012 May;66(5):294-5. doi: 10.1111/j.1600-0536.2012.02009.x. [22486572 ]
  6. Mitra R, Das S, Shinde SV, Sinha S, Somasundaram K, Samuelson AG: Anticancer activity of hydrogen-bond-stabilized half-sandwich Ru(II) complexes with heterocycles. Chemistry. 2012 Sep 24;18(39):12278-91. doi: 10.1002/chem.201200938. Epub 2012 Aug 17. [22903299 ]
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  8. Parham H, Zargar B, Shiralipour R: Fast and efficient removal of mercury from water samples using magnetic iron oxide nanoparticles modified with 2-mercaptobenzothiazole. J Hazard Mater. 2012 Feb 29;205-206:94-100. doi: 10.1016/j.jhazmat.2011.12.026. Epub 2011 Dec 17. [22244341 ]
  9. LITVINCHUK MD: [EFFECT OF 2-MERCAPTOBENZOTHIAZOLE (CAPTAX) ON THE BIL-SECRETORY ACTIVITY OF THE LIVER]. Farmakol Toksikol. 1964 Jul-Aug;27:493-5. [14193129 ]
  10. Roy DK, Bose SK, Geetharani K, Varma Chakrahari KK, Mobin SM, Ghosh S: Synthesis and structural characterization of new divanada- and diniobaboranes containing chalcogen atoms. Chemistry. 2012 Aug 6;18(32):9983-91. doi: 10.1002/chem.201200189. Epub 2012 Jul 10. [22782697 ]
  11. Joseph R, Kumar KG: Electrochemical sensing of acyclovir at a gold electrode modified with 2-mercaptobenzothiazole-[5,10,15,20-tetrakis-(3-methoxy-4-hydroxyphenyl)porphyrin ato]copper(II). Anal Sci. 2011;27(1):67-72. [21233563 ]
  12. Ahuja V, Wanner R, Platzek T, Stahlmann R: Appraisal of the sensitising potential of orally and dermally administered mercaptobenzothiazole by a biphasic protocol of the local lymph node assay. Arch Toxicol. 2009 Oct;83(10):933-9. doi: 10.1007/s00204-009-0426-y. Epub 2009 Apr 19. [19381614 ]
  13. Al-Ansari MM, Steevensz A, Taylor KE, Bewtra JK, Biswas N: Soybean peroxidase-catalyzed removal of an aromatic thiol, 2-mercaptobenzothiazole, from water. Water Environ Res. 2010 Nov;82(11):2285-9. [21141391 ]
  14. Fu XC, Chen X, Guo Z, Xie CG, Kong LT, Liu JH, Huang XJ: Stripping voltammetric detection of mercury(II) based on a surface ion imprinting strategy in electropolymerized microporous poly(2-mercaptobenzothiazole) films modified glassy carbon electrode. Anal Chim Acta. 2011 Jan 24;685(1):21-8. doi: 10.1016/j.aca.2010.11.020. Epub 2010 Nov 21. [21168547 ]
  15. Chen KJ, Lu CJ: A vapor sensor array using multiple localized surface plasmon resonance bands in a single UV-vis spectrum. Talanta. 2010 Jun 15;81(4-5):1670-5. doi: 10.1016/j.talanta.2010.03.023. Epub 2010 Mar 19. [20441956 ]
  16. Kuchta T, Bujdakova H, Sidoova E: Inhibition of yeast-mycelium transformation by 2-alkylthio-6-amino- and 2-alkylthio-6-formamidobenzothiazoles and their in vitro antifungal activity. Folia Microbiol (Praha). 1989;34(6):504-10. [2635130 ]
  17. Li N, Fang G, Liu B, Zhang J, Zhao L, Wang S: A novel hydrophobic task specific ionic liquid for the extraction of Cd(II) from water and food samples as applied to AAS determination. Anal Sci. 2010;26(4):455-9. [20410568 ]
  18. Ziegler V, Suss E: [The allergenic effect of rubber accelerators tetramethyl thiuram disulfide (TMTD) and mercaptobenzothiazole (MBT)]. Allerg Immunol (Leipz). 1974-1975;20-21(3):281-5. [4283450 ]
  19. Li XH, Tang ZX, Zhang XZ: Molecular structure, IR spectra of 2-mercaptobenzothiazole and 2-mercaptobenzoxazole by density functional theory and ab initio Hartree-Fock calculations. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Sep 15;74(1):168-73. doi: 10.1016/j.saa.2009.05.026. Epub 2009 Jun 6. [19553157 ]
  20. Rajasekharan-Nair R, Moore D, Chalmers K, Wallace D, Diamond LM, Darby L, Armstrong DR, Reglinski J, Spicer MD: S-alkylation of soft scorpionates. Chemistry. 2013 Feb 11;19(7):2487-95. doi: 10.1002/chem.201202314. Epub 2013 Jan 7. [23297136 ]
  21. Perez-Quintanilla D, Del Hierro I, Fajardo M, Sierra I: Preparation of 2-mercaptobenzothiazole-derivatized mesoporous silica and removal of Hg(ii) from aqueous solution. J Environ Monit. 2006 Jan;8(1):214-22. Epub 2005 Nov 9. [16395482 ]
  22. Astigarraga E, Barreda-Gomez G, Lombardero L, Fresnedo O, Castano F, Giralt MT, Ochoa B, Rodriguez-Puertas R, Fernandez JA: Profiling and imaging of lipids on brain and liver tissue by matrix-assisted laser desorption/ ionization mass spectrometry using 2-mercaptobenzothiazole as a matrix. Anal Chem. 2008 Dec 1;80(23):9105-14. doi: 10.1021/ac801662n. [18959430 ]
  23. Kuchta T, Strakova H, Sidoova E: [Inhibition of Candida albicans transformation from the yeast form to the mycelial form by 2-alkylthio-6-amino- and 2-alkylthio-6-formamido- benzothiazoles]. Cesk Farm. 1989 Apr;38(3):139-40. [2673553 ]
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  25. Metsios A, Verginadis I, Simos Y, Batistatou A, Peschos D, Ragos V, Vezyraki P, Evangelou A, Karkabounas S: Cytotoxic and anticancer effects of the triorganotin compound [(C(6)H(5))(3)Sn(cmbzt)]: an in vitro, ex vivo and in vivo study. Eur J Pharm Sci. 2012 Sep 29;47(2):490-6. doi: 10.1016/j.ejps.2012.07.011. Epub 2012 Jul 24. [22841513 ]
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  27. Azam MA, Suresh B: Biological activities of 2-mercaptobenzothiazole derivatives: a review. Sci Pharm. 2012 Dec;80(4):789-823. doi: 10.3797/scipharm.1204-27. Epub 2012 Jun 18. [23264933 ]
  28. Song C, Wang Z, Yang J, Zhang R, Cui Y: Preparation of 2-mercaptobenzothiazole-labeled immuno-Au aggregates for SERS-based immunoassay. Colloids Surf B Biointerfaces. 2010 Nov 1;81(1):285-8. doi: 10.1016/j.colsurfb.2010.07.023. Epub 2010 Jul 15. [20688492 ]
  29. Pourreza N, Ghanemi K: Solid phase extraction of cadmium on 2-mercaptobenzothiazole loaded on sulfur powder in the medium of ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate and cold vapor generation-atomic absorption spectrometric determination. J Hazard Mater. 2010 Jun 15;178(1-3):566-71. doi: 10.1016/j.jhazmat.2010.01.122. Epub 2010 Feb 1. [20176439 ]
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Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.29 uMNVS_ADME_hCYP2B6Novascreen
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 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.6 uMNVS_ADME_hCYP2C19Novascreen
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 ]
General Function:
Transcription regulatory region dna binding
Specific Function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
Gene Name:
AHR
Uniprot ID:
P35869
Molecular Weight:
96146.705 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC508.17 uMATG_Ahr_CISAttagene
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 ]