Hmdb loader

Showing metabocard for Benzothiazole (HMDB0032930)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:43 UTC
Update Date2023-02-21 17:22:48 UTC
HMDB IDHMDB0032930
Secondary Accession Numbers
  • HMDB32930
Metabolite Identification
Common NameBenzothiazole
DescriptionBenzothiazole, also known as BT or benzosulfonazole, 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). This ring is a potential component in nonlinear optics (NLO). The nine atoms of the bicycle and the attached substituents are coplanar. Although the parent compound, benzothiazole is not widely used, many of its derivatives are found in commercial products or in nature. Benzothiazole is a coffee, cooked, and gasoline tasting compound. benzothiazole is found, on average, in the highest concentration in safflowers. benzothiazole has also been detected, but not quantified, in several different foods, such as common persimmons, fruits, guava, potato, and tea. This could make benzothiazole a potential biomarker for the consumption of these foods. Firefly luciferin can be considered a derivative of benzothiazole. The compound is used also used as an insecticide and food flavoring agent. Some drugs contain this group, examples being riluzole and pramipexole. It is colorless, slightly viscous liquid. It is a thermally stable electron-withdrawing moiety with numerous applications in dyes such as thioflavin. Benzothiazole is an aromatic heterocyclic compound with the chemical formula C7H5NS.
Structure
Data?1677000168
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032930 (Benzothiazole)


  Mrv1652305271900032D          

  9 10  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0032930 (Benzothiazole)

HMDB0032930
     RDKit          3D
Benzothiazole
 14 15  0  0  0  0  0  0  0  0999 V2000
   -1.6022   -0.9524   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0369    0.3091    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0283    1.2242    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235    0.8512    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8326    1.6198    0.4913 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8662    0.3011    0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0021   -0.6495   -0.1449 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162   -0.4094   -0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972   -1.3395   -0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3928   -1.6908   -0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0686    0.6130    0.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2176    2.2488    0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9744    0.2466    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0712   -2.3720   -0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  1  1  0
  8  4  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  6 13  1  0
  9 14  1  0
M  END
Download

3D SDF for HMDB0032930 (Benzothiazole)


  Mrv1652305271900032D          

  9 10  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032930

> <DATABASE_NAME>
hmdb

> <SMILES>
S1C=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H

> <INCHI_KEY>
IOJUPLGTWVMSFF-UHFFFAOYSA-N

> <FORMULA>
C7H5NS

> <MOLECULAR_WEIGHT>
135.186

> <EXACT_MASS>
135.014269855

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
13.613239251755525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-benzothiazole

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
2.1134717653333333

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.277467273992971

> <JCHEM_POLAR_SURFACE_AREA>
12.89

> <JCHEM_REFRACTIVITY>
37.128699999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzothiazole

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0032930 (Benzothiazole)

HMDB0032930
     RDKit          3D
Benzothiazole
 14 15  0  0  0  0  0  0  0  0999 V2000
   -1.6022   -0.9524   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0369    0.3091    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0283    1.2242    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235    0.8512    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8326    1.6198    0.4913 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8662    0.3011    0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0021   -0.6495   -0.1449 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162   -0.4094   -0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972   -1.3395   -0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3928   -1.6908   -0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0686    0.6130    0.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2176    2.2488    0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9744    0.2466    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0712   -2.3720   -0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  1  1  0
  8  4  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  6 13  1  0
  9 14  1  0
M  END
Download

PDB for HMDB0032930 (Benzothiazole)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM    9  S   UNK     0       2.126   4.089   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    7                                                       
CONECT    5    8    9                                                       
CONECT    6    3    7    8                                                  
CONECT    7    4    6    9                                                  
CONECT    8    5    6                                                       
CONECT    9    5    7                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   20    0
END
Download

3D PDB for HMDB0032930 (Benzothiazole)

COMPND    HMDB0032930
HETATM    1  C1  UNL     1      -1.602  -0.952  -0.299  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.037   0.309   0.048  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.028   1.224   0.325  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.323   0.851   0.246  1.00  0.00           C  
HETATM    5  S1  UNL     1       1.833   1.620   0.491  1.00  0.00           S  
HETATM    6  C5  UNL     1       2.866   0.301   0.139  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.002  -0.650  -0.145  1.00  0.00           N  
HETATM    8  C6  UNL     1       0.716  -0.409  -0.102  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.297  -1.340  -0.383  1.00  0.00           C  
HETATM   10  H1  UNL     1      -2.393  -1.691  -0.522  1.00  0.00           H  
HETATM   11  H2  UNL     1      -3.069   0.613   0.114  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.218   2.249   0.610  1.00  0.00           H  
HETATM   13  H4  UNL     1       3.974   0.247   0.145  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.071  -2.372  -0.670  1.00  0.00           H  
CONECT    1    2    2    9   10
CONECT    2    3   11
CONECT    3    4    4   12
CONECT    4    5    8
CONECT    5    6
CONECT    6    7    7   13
CONECT    7    8
CONECT    8    9    9
CONECT    9   14
END
Download

SMILES for HMDB0032930 (Benzothiazole)

S1C=NC2=CC=CC=C12
Download

INCHI for HMDB0032930 (Benzothiazole)

InChI=1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
1-Thia-3-azaindeneChEBI
BenzosulfonazoleChEBI
BenzothiazolChEBI
BTChEBI
BenzosulphonazoleGenerator
1,3-BenzothiazoleHMDB
BOTHMDB
Vangard BTHMDB
Chemical FormulaC7H5NS
Average Molecular Weight135.186
Monoisotopic Molecular Weight135.014269855
IUPAC Name1,3-benzothiazole
Traditional Namebenzothiazole
CAS Registry Number95-16-9
SMILES
S1C=NC2=CC=CC=C12
InChI Identifier
InChI=1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H
InChI KeyIOJUPLGTWVMSFF-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
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point2 °CNot Available
Boiling Point231.00 to 233.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4.3 mg/mL at 25 °CNot Available
LogP2.01Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.76 g/LALOGPS
logP2.13ALOGPS
logP2.11ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)2.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.13 m³·mol⁻¹ChemAxon
Polarizability13.61 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.02431661259
DarkChem[M-H]-120.39831661259
DeepCCS[M-2H]-155.44930932474
DeepCCS[M+Na]+130.30630932474
AllCCS[M+H]+125.232859911
AllCCS[M+H-H2O]+120.332859911
AllCCS[M+NH4]+129.732859911
AllCCS[M+Na]+131.032859911
AllCCS[M-H]-121.932859911
AllCCS[M+Na-2H]-123.432859911
AllCCS[M+HCOO]-125.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.67 minutes32390414
Predicted by Siyang on May 30, 202210.9688 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.22 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid83.9 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1526.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid406.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid142.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid278.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid174.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid390.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid530.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)216.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid874.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid288.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1187.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid273.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid330.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate519.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA283.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water144.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzothiazoleS1C=NC2=CC=CC=C121904.5Standard polar33892256
BenzothiazoleS1C=NC2=CC=CC=C121204.7Standard non polar33892256
BenzothiazoleS1C=NC2=CC=CC=C121208.2Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010915
KNApSAcK IDC00052216
Chemspider ID6952
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzothiazole
METLIN IDNot Available
PubChem Compound7222
PDB IDNot Available
ChEBI ID45993
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1007521
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wallqvist A, Monks A, Rabow AA, Thanki N, Shoemaker RH, Covell DG: Mining the NCI screening database: explorations of agents involved in cell cycle regulation. Prog Cell Cycle Res. 2003;5:173-9. [PubMed:14593711 ]
  2. Alang G, Kaur G, Kaur R, Singh A, Tiwari R: Synthesis, Characterization, and Biological Evaluation of certain 6-methyl-2(3H)-benzo-1, 3-thiazolyl-1'-ethylidene-2-(o, p- Substituted Acetophenones) Hydrazine Analogs. J Young Pharm. 2010 Oct;2(4):394-8. doi: 10.4103/0975-1483.71636. [PubMed:21264101 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .