N-Acetyl sulfamethoxazole (CHEM020254)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:57:26 UTC
Update Date2016-10-28 10:03:52 UTC
Accession NumberCHEM020254
Identification
Common NameN-Acetyl sulfamethoxazole
ClassSmall Molecule
DescriptionA sulfonamide compound having a 4-acetamidophenyl group attached to the sulfur atom and a 1,2-oxazol-3-yl group attached to the nitrogen atom.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • Suspected Compounds - Waste Water
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4'-((5-Methyl-3-isoxazolyl)sulfamoyl)acetanilideChEBI
AcetylsulfamethoxazoleChEBI
GantanolChEBI
N(4)-AcetylsulfisomezoleChEBI
N(4)-AcetylsulfulfamethoxazoleChEBI
SMX-AcetateChEBI
Sulfamethoxazole acetateChEBI
Sulfisomezole-N(4)-acetateChEBI
4'-((5-Methyl-3-isoxazolyl)sulphamoyl)acetanilideGenerator
AcetylsulphamethoxazoleGenerator
N(4)-AcetylsulphisomezoleGenerator
N(4)-AcetylsulphulfamethoxazoleGenerator
SMX-Acetic acidGenerator
Sulfamethoxazole acetic acidGenerator
Sulphamethoxazole acetateGenerator
Sulphamethoxazole acetic acidGenerator
Sulfisomezole-N(4)-acetic acidGenerator
Sulphisomezole-N(4)-acetateGenerator
Sulphisomezole-N(4)-acetic acidGenerator
N4-AcetylsulphamethoxazoleGenerator
N-{4-[(5-methylisoxazol-3-yl)sulfamoyl]phenyl}acetamideHMDB
N4-AcetylsulfisomezoleHMDB
N4-AcetylsulfulfamethoxazoleHMDB
Sulfisomezole-N4-acetateHMDB
N(4)-AcetylsulfamethoxazoleHMDB
N(4)-AcetylsulphamethoxazoleHMDB
N-AcetylsulphamethoxazoleHMDB
N4-AcetylsulfamethoxazoleChEBI
Chemical FormulaC12H13N3O4S
Average Molecular Mass295.314 g/mol
Monoisotopic Mass295.063 g/mol
CAS Registry Number21312-10-7
IUPAC NameN-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}ethanimidic acid
Traditional NameN(sup 4)-acetylsulfisomezole
SMILESCC(O)=NC1=CC=C(C=C1)S(=O)(=O)NC1=NOC(C)=C1
InChI IdentifierInChI=1S/C12H13N3O4S/c1-8-7-12(14-19-8)15-20(17,18)11-5-3-10(4-6-11)13-9(2)16/h3-7H,1-2H3,(H,13,16)(H,14,15)
InChI KeyGXPIUNZCALHVBA-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
  • Imidolactam
  • Azole
  • Isoxazole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Heteroaromatic compound
  • Sulfonyl
  • Aminosulfonyl compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organosulfur compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP1.13ALOGPS
logP1.58ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)5.68ChemAxon
pKa (Strongest Basic)0.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.79 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity75.41 m³·mol⁻¹ChemAxon
Polarizability28.51 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-9360000000-1c2a094865717e2eaddeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9231000000-4a60dfa1fba628eae89eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0007-0490000000-52c719984f40afb2fe69Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0900000000-885f5298dc9cac736ad2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-3845d94430e55b3672ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-0f28bd7306e116b23664Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-a931f6f79851f6517143Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0390000000-dba8d5adc6ad93ec8917Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-72a1ece66e1150c7e39eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000t-0900000000-a95d8aa5899e8bda0fe6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-34815ffdbcd4883ad2ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-1900000000-1f10de1f050b43bd0fc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000x-6900000000-6d4e7909426bd265f9caSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0290000000-71d5ce544864c89f38cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-43bf3d487b565393cd9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000t-0900000000-b0416b270d76be397989Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-25b614db8f59a5f5db39Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-2900000000-626694102c1eea16e5a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-7ce29f406bc6d908f6eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-5c819656360e2573a7d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-59a88d63e4fe9a3c607fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-dafe8db52ffd9aba90dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 80V, Negativesplash10-0002-0900000000-5c819656360e2573a7d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-0900000000-72a1ece66e1150c7e39eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-000t-0900000000-a95d8aa5899e8bda0fe6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 55V, Negativesplash10-0002-0900000000-7ce29f406bc6d908f6eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0002-0900000000-59a88d63e4fe9a3c607fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013854
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID58771
ChEBI ID31169
PubChem Compound ID80641
Kegg Compound IDC13061
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10843725
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15545312
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15984773
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2022750
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2040608
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21351294
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24875872
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=8062495
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=8807056
10. Gobel A, McArdell CS, Suter MJ, Giger W: Trace determination of macrolide and sulfonamide antimicrobials, a human sulfonamide metabolite, and trimethoprim in wastewater using liquid chromatography coupled to electrospray tandem mass spectrometry. Anal Chem. 2004 Aug 15;76(16):4756-64. doi: 10.1021/ac0496603.
11. Asper R, Schmucki O: Critical aspects of urine and stone analysis. Appearance of iatrogenic urinary calculi. Urol Int. 1986;41(5):334-42. doi: 10.1159/000281233.
12. Weber A, Opheim KE, Siber GR, Ericson JF, Smith AL: High-performance liquid chromatographic quantitation of trimethoprim, sulfamethoxazole, and N4-acetylsulfamethoxazole in body fluids. J Chromatogr. 1983 Dec 9;278(2):337-45. doi: 10.1016/s0378-4347(00)84793-3.
13. Vree TB, Hekster YA, Baars AM, Damsma JE, Kleijin EV: Determination of trimethoprim and sulfamethoxazole (co-trimoxazole) in body fluids of man by means of high-performance liquid chromatography. J Chromatogr. 1978 Jul 1;146(1):103-12. doi: 10.1016/s0378-4347(00)81294-3.