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Record Information
Version2.0
Creation Date2014-09-11 05:17:35 UTC
Update Date2014-12-24 20:26:57 UTC
Accession NumberT3D4810
Identification
Common NameN-Butyl-Benzenesulfonamide
ClassSmall Molecule
DescriptionN-Butyl benzenesulfonamide (NBBS), a plasticizer used commercially in the polymerization of polyamide compounds. It is neurotoxic and has been found to induce spastic myelopathy in rabbits.
Compound Type
  • Amide
  • Industrial/Workplace Toxin
  • Organic Compound
  • Plasticizer
  • Synthetic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC10H15NO2S
Average Molecular Mass213.297 g/mol
Monoisotopic Mass213.082 g/mol
CAS Registry Number3622-84-2
IUPAC NameN-butylbenzenesulfonamide
Traditional NameN-butyl-benzenesulfonamide
SMILESCCCCNS(=O)(=O)C1=CC=CC=C1
InChI IdentifierInChI=1S/C10H15NO2S/c1-2-3-9-11-14(12,13)10-7-5-4-6-8-10/h4-8,11H,2-3,9H2,1H3
InChI KeyInChIKey=IPRJXAGUEGOFGG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Organosulfonic acid amide
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • 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 PointNot Available
Boiling Point314°C
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP1.83ALOGPS
logP2.13ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)10.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.17 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.99 m³·mol⁻¹ChemAxon
Polarizability22.66 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-cd5f37e36b479444f0f9JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-ac17d7bd97de41746cb5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-4b3fba1a84e8a9817ce9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-0be94919e879316d19cdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-b21e55783effd7b7e375JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052g-5900000000-5d23dc1ef544f9511251JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052f-5900000000-2fa472f57a904ec60c24JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4390000000-fb042a5e10a6b299aab5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200000000-a8348044b7d5917c69a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-5d5130787a19b8df715dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0190000000-48cfcfa90253b362d61eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-2940000000-174036b1d03d03f8c06aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9400000000-c79d7477aa40e59f480bJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00bc-8900000000-6d3edc2b6cee3acc8852JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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/SourcesN-Butyl benzenesulfonamide (NBBS), a plasticizer used commercially in the polymerization of polyamide compounds. It is neurotoxic and has been found to induce spastic myelopathy in rabbits.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB02055
HMDB IDNot Available
PubChem Compound ID19241
ChEMBL IDCHEMBL479880
ChemSpider ID18156
KEGG IDNot Available
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
MSDST3D4810.pdf
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.0678 uMTox21_AR_BLA_Antagonist_ratioTox21/NCGC
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 ]