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Showing NP-Card for 2-Benzothiazolinone (NP0084774)

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Record Information
Version2.0
Created at2022-04-29 05:25:45 UTC
Updated at2022-04-29 05:25:45 UTC
NP-MRD IDNP0084774
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Benzothiazolinone
Description2-Hydroxybenzothiazole, also known as 2(3H)-benzothiazolone or HBT, 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-Hydroxybenzothiazole is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Benzothiazolinone is found in Cucumis sativus and Cucumis sativus . 2-Benzothiazolinone was first documented in 1998 (PMID: 9544213). Benzothiazole substituted with a hydroxy group at the 2-position (PMID: 15750776) (PMID: 18568896) (PMID: 23224221).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0084774 (2-Benzothiazolinone)


  Mrv1533004171500062D          

 10 11  0  0  0  0            999 V2000
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
Download

3D MOL for NP0084774 (2-Benzothiazolinone)

     RDKit          3D

 15 16  0  0  0  0  0  0  0  0999 V2000
    3.9142    0.4938   -0.0663 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066    0.4370    0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6644   -0.3857   -0.5317 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.2832   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6129   -1.1047   -0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9366   -0.8897   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587    0.1278    0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3936    0.9404    0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395    0.7298    0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483    1.4614    0.9184 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5004    0.0037    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3398   -1.9403   -1.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6760   -1.5762   -1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020    0.2370    0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.7488    1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  2  1  0
  9  4  1  0
  1 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
M  END
Download

3D SDF for NP0084774 (2-Benzothiazolinone)


  Mrv1533004171500062D          

 10 11  0  0  0  0            999 V2000
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=NC2=CC=CC=C2S1

> <INCHI_IDENTIFIER>
InChI=1S/C7H5NOS/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)

> <INCHI_KEY>
YEDUAINPPJYDJZ-UHFFFAOYSA-N

> <FORMULA>
C7H5NOS

> <MOLECULAR_WEIGHT>
151.18

> <EXACT_MASS>
151.009184959

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
14.669035262989738

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-benzothiazol-2-ol

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
2.4941564486666663

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.436227223534233

> <JCHEM_PKA_STRONGEST_BASIC>
0.02706611235203249

> <JCHEM_POLAR_SURFACE_AREA>
33.120000000000005

> <JCHEM_REFRACTIVITY>
38.5829

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-benzothiazolone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0084774 (2-Benzothiazolinone)

Download
PDB for NP0084774 (2-Benzothiazolinone)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0       2.126  -2.549   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    8    4   10                                                  
CONECT   10    9    2                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0084774 (2-Benzothiazolinone)
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SMILES for NP0084774 (2-Benzothiazolinone)
OC1=NC2=CC=CC=C2S1
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INCHI for NP0084774 (2-Benzothiazolinone)
InChI=1S/C7H5NOS/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
(2-Mercatophenyl)carbamothioic acid gamma-lactoneChEBI
2(3H)-BenzothiazoloneChEBI
2-BenzothiazololChEBI
2-BenzothiazoloneChEBI
2-Hydroxy-1,3-benzothiazoleChEBI
3H-Benzothiazol-2-oneChEBI
HBTChEBI
HOBTChEBI
(2-Mercatophenyl)carbamothioate g-lactoneGenerator
(2-Mercatophenyl)carbamothioate gamma-lactoneGenerator
(2-Mercatophenyl)carbamothioate γ-lactoneGenerator
(2-Mercatophenyl)carbamothioic acid g-lactoneGenerator
(2-Mercatophenyl)carbamothioic acid γ-lactoneGenerator
Chemical FormulaC7H5NOS
Average Mass151.1800 Da
Monoisotopic Mass151.00918 Da
IUPAC Name1,3-benzothiazol-2-ol
Traditional Name2-benzothiazolone
CAS Registry NumberNot Available
SMILES
OC1=NC2=CC=CC=C2S1
InChI Identifier
InChI=1S/C7H5NOS/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
InChI KeyYEDUAINPPJYDJZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cucumis sativusLOTUS Database
Cucumis sativus L.Plant
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
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen 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
logP2.12ALOGPS
logP2.49ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)8.44ChemAxon
pKa (Strongest Basic)0.027ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.58 m³·mol⁻¹ChemAxon
Polarizability14.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13625  
PDB IDNot Available
ChEBI ID115196  
Good Scents IDNot Available
References
General References
  1. Nawrocki ST, Drake KD, Watson CF, Foster GD, Maier KJ: Comparative aquatic toxicity evaluation of 2-(thiocyanomethylthio)benzothiazole and selected degradation products using Ceriodaphnia dubia. Arch Environ Contam Toxicol. 2005 Apr;48(3):344-50. doi: 10.1007/s00244-004-0105-1. Epub 2005 Feb 15. [PubMed:15750776  ] 
  2. 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  ] 
  3. Kamps JJ, Belle R, Mecinovic J: Hydroxylamine as an oxygen nucleophile: substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides. Org Biomol Chem. 2013 Feb 21;11(7):1103-8. doi: 10.1039/c2ob26929e. [PubMed:23224221  ] 
  4. Ucar H, Van derpoorten K, Cacciaguerra S, Spampinato S, Stables JP, Depovere P, Isa M, Masereel B, Delarge J, Poupaert JH: Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives. J Med Chem. 1998 Mar 26;41(7):1138-45. doi: 10.1021/jm970682+. [PubMed:9544213  ]