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Showing NP-Card for rokon (NP0247834)

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Record Information
Version2.0
Created at2022-09-07 09:49:20 UTC
Updated at2022-09-07 09:49:21 UTC
NP-MRD IDNP0247834
Secondary Accession NumbersNone
Natural Product Identification
Common Namerokon
Description2(3H)-Benzothiazolethione, also known as captax or 2-mercaptobenzothiazole, 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). 2(3H)-Benzothiazolethione is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2(3H)-Benzothiazolethione has been detected, but not quantified in, fruits. This could make 2(3H)-benzothiazolethione a potential biomarker for the consumption of these foods. 2(3H)-Benzothiazolethione is a potentially toxic compound. rokon was first documented in 2008 (PMID: 18568896). 1,3-Benzothiazole substituted at the 2-position with a sulfanyl group (PMID: 19158128) (PMID: 23063874) (PMID: 23178179) (PMID: 23340394) (PMID: 20692014) (PMID: 20420816).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0247834 (rokon)


  Mrv0541 05061305182D          

 10 11  0  0  0  0            999 V2000
   -1.3741    1.8023    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6097    1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086    0.3563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770   -0.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -1.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9851   -1.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7758   -1.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9670   -0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3676   -0.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879    0.7376    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for NP0247834 (rokon)

     RDKit          3D

 15 16  0  0  0  0  0  0  0  0999 V2000
    4.3118    0.4532    0.1653 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576    0.4821    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8367   -0.5499    0.0025 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5326   -0.3254   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5032   -1.2897   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8057   -0.8834   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2294    0.4006   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270    1.3576    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268    0.9766    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6068    1.8185    0.2123 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655   -1.5368   -0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2985   -2.3424   -0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5866   -1.6388   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474    0.6848   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4399    2.3930    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
 10  2  1  0
  5  4  1  0
  3 11  1  0
  8 15  1  0
  7 14  1  0
  6 13  1  0
  5 12  1  0
M  END
Download

3D SDF for NP0247834 (rokon)


  Mrv0541 05061305182D          

 10 11  0  0  0  0            999 V2000
   -1.3741    1.8023    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6097    1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086    0.3563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770   -0.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -1.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9851   -1.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7758   -1.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9670   -0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3676   -0.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879    0.7376    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
S=C1NC2=C(S1)C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C7H5NS2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)

> <INCHI_KEY>
YXIWHUQXZSMYRE-UHFFFAOYSA-N

> <FORMULA>
C7H5NS2

> <MOLECULAR_WEIGHT>
167.251

> <EXACT_MASS>
166.986340545

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.888767164331263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydro-1,3-benzothiazole-2-thione

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.879384047333333

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.898007105435802

> <JCHEM_PKA_STRONGEST_BASIC>
-2.162116074374314

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
50.69840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2(3H)-benzothiazolethione

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0247834 (rokon)

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PDB for NP0247834 (rokon)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  S   UNK     0      -2.565   3.364   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0      -3.005   1.889   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.069   0.665   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.944  -0.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.587  -2.101   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.706  -3.159   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.181  -2.719   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.538  -1.221   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.420  -0.163   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0      -4.457   1.377   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0247834 (rokon)
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SMILES for NP0247834 (rokon)
S=C1NC2=C(S1)C=CC=C2
Download
INCHI for NP0247834 (rokon)
InChI=1S/C7H5NS2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
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View in JSmol
Synonyms
ValueSource
1,3-Benzothiazol-2-yl hydrosulfideChEBI
2-BenzothiazolethiolChEBI
2-MBTChEBI
2-MercaptobenzothiazoleChEBI
2-Sulfanyl-1,3-benzothiazoleChEBI
Benzothiazole-2-thiolChEBI
BenzothiazolethiolChEBI
Benzothiazolyl mercaptanChEBI
CaptaxChEBI
MBTChEBI
MercaptobenzothiazoleChEBI
1,3-Benzothiazol-2-yl hydrosulphideGenerator
2-Sulphanyl-1,3-benzothiazoleGenerator
1,3-Benzothiazole-2-thiolHMDB
155-04-4 (Zinc salt)HMDB
2(3H)-Benzothiazolethione, potassium saltHMDB
2-BenzothiazolethioneHMDB
2-BenzothiazolinethioneHMDB
2-Benzothiazolyl mercaptanHMDB
2-Mercapto-benzothiazoleHMDB
2-Mercaptobenzothiazole (2-MBT)HMDB
2-Mercaptobenzothiazole (in liquid mixtures)HMDB
2-MercaptobenzthiazoleHMDB
2-MercptobenzothiazoleHMDB
2-MerkaptobenzotiazolHMDB
2-MerkaptobenzthiazolHMDB
2-ThiobenzothiazoleHMDB
4162-43-0 (Copper(+2) salt)HMDB
7778-70-3 (Potassium salt)HMDB
Accel mHMDB
Accelerator mHMDB
Accelerator mercaptoHMDB
Benzothiazole-2-thioneHMDB
Captax, bismuth(+3) saltHMDB
Captax, cobalt(+2) saltHMDB
Captax, copper(+2) saltHMDB
Captax, lead(+2) saltHMDB
Captax, mercury (+2) saltHMDB
Captax, potassium saltHMDB
Captax, silver(+1) saltHMDB
Captax, sodium saltHMDB
Captax, zinc saltHMDB
DermacidHMDB
DrmacidHMDB
Ekagom gHMDB
KaptaksHMDB
KaptaxHMDB
MBT, CaptaxHMDB
MebetizolHMDB
MebetizoleHMDB
MebithizolHMDB
Mercapto-benzothiazoleHMDB
MercaptobenzothiazolHMDB
MercaptobenzthiazoleHMDB
MertaxHMDB
Nocceler mHMDB
Nuodeb 84HMDB
Nuodex 84HMDB
Pennac MBTHMDB
Pennac MBT powderHMDB
Perkacit MBTHMDB
Pneumax MBTHMDB
RokonHMDB
RotaxHMDB
Royal MBTHMDB
Soxinol mHMDB
SulfadeneHMDB
Thiot axHMDB
ThiotaxHMDB
Vulkacit mHMDB
Vulkacit m, vulkacit merkapto/cHMDB
Vulkacit mercaptoHMDB
Vulkacit mercapto/cHMDB
Chemical FormulaC7H5NS2
Average Mass167.2510 Da
Monoisotopic Mass166.98634 Da
IUPAC Name2,3-dihydro-1,3-benzothiazole-2-thione
Traditional Name2(3H)-benzothiazolethione
CAS Registry NumberNot Available
SMILES
S=C1NC2=C(S1)C=CC=C2
InChI Identifier
InChI=1S/C7H5NS2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
InChI KeyYXIWHUQXZSMYRE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0030524  
DrugBank IDDB11496  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002396  
KNApSAcK IDNot Available
Chemspider ID13802256  
KEGG Compound IDC14437  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21831736  
PDB IDNot Available
ChEBI ID34292  
Good Scents IDNot Available
References
General References
  1. Chipinda I, Zhang XD, Simoyi RH, Siegel PD: Mercaptobenzothiazole allergenicity-role of the thiol group. Cutan Ocul Toxicol. 2008;27(2):103-16. doi: 10.1080/15569520701713008. [PubMed:18568896  ] 
  2. Sorahan T: Cancer risks in chemical production workers exposed to 2-mercaptobenzothiazole. Occup Environ Med. 2009 Apr;66(4):269-73. doi: 10.1136/oem.2008.041400. Epub 2009  Jan 21. [PubMed:19158128  ] 
  3. Corsini E, Galbiati V, Mitjans M, Galli CL, Marinovich M: NCTC 2544 and IL-18 production: a tool for the identification of contact allergens. Toxicol In Vitro. 2013 Apr;27(3):1127-34. doi: 10.1016/j.tiv.2012.05.018. Epub  2012 Oct 9. [PubMed:23063874  ] 
  4. Tietge JE, Degitz SJ, Haselman JT, Butterworth BC, Korte JJ, Kosian PA, Lindberg-Livingston AJ, Burgess EM, Blackshear PE, Hornung MW: Inhibition of the thyroid hormone pathway in Xenopus laevis by 2-mercaptobenzothiazole. Aquat Toxicol. 2013 Jan 15;126:128-36. doi: 10.1016/j.aquatox.2012.10.013. Epub  2012 Oct 29. [PubMed:23178179  ] 
  5. Fransway AF, Zug KA, Belsito DV, Deleo VA, Fowler JF Jr, Maibach HI, Marks JG, Mathias CG, Pratt MD, Rietschel RL, Sasseville D, Storrs FJ, Taylor JS, Warshaw EM, Dekoven J, Zirwas M: North American Contact Dermatitis Group patch test results for 2007-2008. Dermatitis. 2013 Jan-Feb;24(1):10-21. doi: 10.1097/DER.0b013e318277ca50. [PubMed:23340394  ] 
  6. El-Bassi L, Iwasaki H, Oku H, Shinzato N, Matsui T: Biotransformation of benzothiazole derivatives by the Pseudomonas putida strain HKT554. Chemosphere. 2010 Sep;81(1):109-13. doi: 10.1016/j.chemosphere.2010.07.024. Epub  2010 Aug 6. [PubMed:20692014  ] 
  7. Teuber K, Schiller J, Fuchs B, Karas M, Jaskolla TW: Significant sensitivity improvements by matrix optimization: a MALDI-TOF mass spectrometric study of lipids from hen egg yolk. Chem Phys Lipids. 2010 Jun;163(6):552-60. doi: 10.1016/j.chemphyslip.2010.04.005.  Epub 2010 Apr 24. [PubMed:20420816  ] 
  8. Wang F, Cai S, Wang Z, Xi C: Synthesis of 2-mercaptobenzothiazoles via DBU-promoted tandem reaction of o-haloanilines and carbon disulfide. Org Lett. 2011 Jun 17;13(12):3202-5. doi: 10.1021/ol2011105. Epub 2011 May 17. [PubMed:21591631  ] 
  9. LOTUS database [Link]