Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:14 UTC
Update Date2020-07-06 16:00:59 UTC
HMDB IDHMDB0013854
Secondary Accession Numbers
  • HMDB13854
Metabolite Identification
Common NameN4-Acetylsulfamethoxazole
DescriptionN4-Acetylsulfamethoxazole is a metabolite of the sulfonamide bacteriostatic antibiotic sulfamethoxazole. Sulfamethoxazole is metabolized via acetylation catalyzed by liver extramitochondrial N-acetyl transferases. Acetylsulfamethoxazole is excreted in urine. Acetylsulfamethoxazole and sulfamethoxazole can be used as a probe for the molecular percentage enrichment of liver extramitochondrial acetyl-CoA. N4-Acetylsulfamethoxazole can be used as a reference for measuring sulfamethoxazole impurities and waste determination (PMID: 15307787 ). It is one of the critical aspects of urine and stone analysis (PMID: 3811034 ) and its quantitative determination in body fluids could be performed by reversed-phase high-performance liquid chromatography, a rapid, precise and simple procedure (PMID: 6668314 ). It is also reported the renal excretion rate of the metabolite N4-acetylsulfamethoxazole is not dependent on the urinary pH (PMID: 670346 ). N4-Acetylsulfamethoxazole is only found in individuals who have consumed the drug sulfamethoxazole.
Structure
Data?1582753148
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 Weight295.314
Monoisotopic Molecular Weight295.062676609
IUPAC NameN-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}ethanimidic acid
Traditional NameN(sup 4)-acetylsulfisomezole
CAS Registry Number21312-10-7
SMILES
CC(O)=NC1=CC=C(C=C1)S(=O)(=O)NC1=NOC(C)=C1
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.86Extrapolated
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M-H]-Not Available172.053http://allccs.zhulab.cn/database/detail?ID=AllCCS00001917
AllCCS[M+H]+Not Available171.45http://allccs.zhulab.cn/database/detail?ID=AllCCS00001917
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP10(1.13) g/LALOGPS
logP10(1.58) g/LChemAxon
logS10(-3.1) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.62331661259
DarkChem[M-H]-168.34131661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N4-Acetylsulfamethoxazole,1TMS,#1CC(=NC1=CC=C(S(=O)(=O)NC2=NOC(C)=C2)C=C1)O[Si](C)(C)C2636.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
N4-Acetylsulfamethoxazole,1TMS,#2CC(O)=NC1=CC=C(S(=O)(=O)N(C2=NOC(C)=C2)[Si](C)(C)C)C=C12628.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
N4-Acetylsulfamethoxazole,1TBDMS,#1CC(=NC1=CC=C(S(=O)(=O)NC2=NOC(C)=C2)C=C1)O[Si](C)(C)C(C)(C)C2919.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
N4-Acetylsulfamethoxazole,1TBDMS,#2CC(O)=NC1=CC=C(S(=O)(=O)N(C2=NOC(C)=C2)[Si](C)(C)C(C)(C)C)C=C12881.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N4-Acetylsulfamethoxazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-9360000000-1c2a094865717e2eadde2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N4-Acetylsulfamethoxazole GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9231000000-4a60dfa1fba628eae89e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N4-Acetylsulfamethoxazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-QTOF , negative-QTOFsplash10-0007-0490000000-52c719984f40afb2fe692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-QTOF , negative-QTOFsplash10-0002-0900000000-885f5298dc9cac736ad22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-QTOF , negative-QTOFsplash10-001i-0900000000-3845d94430e55b3672ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-QTOF , negative-QTOFsplash10-001i-0900000000-0f28bd7306e116b236642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-a931f6f79851f65171432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0006-0390000000-dba8d5adc6ad93ec89172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-72a1ece66e1150c7e39e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-000t-0900000000-a95d8aa5899e8bda0fe62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-34815ffdbcd4883ad2dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-001i-1900000000-1f10de1f050b43bd0fc42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-000x-6900000000-6d4e7909426bd265f9ca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0006-0290000000-71d5ce544864c89f38cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-43bf3d487b565393cd9e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-000t-0900000000-b0416b270d76be3979892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-25b614db8f59a5f5db392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-001i-2900000000-626694102c1eea16e5a62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-7ce29f406bc6d908f6ea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-5c819656360e2573a7d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-59a88d63e4fe9a3c607f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-dafe8db52ffd9aba90db2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole 80V, Negative-QTOFsplash10-0002-0900000000-5c819656360e2573a7d62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole 30V, Negative-QTOFsplash10-0002-0900000000-72a1ece66e1150c7e39e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole 45V, Negative-QTOFsplash10-000t-0900000000-a95d8aa5899e8bda0fe62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole 55V, Negative-QTOFsplash10-0002-0900000000-7ce29f406bc6d908f6ea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N4-Acetylsulfamethoxazole 35V, Negative-QTOFsplash10-0002-0900000000-59a88d63e4fe9a3c607f2021-09-20HMDB team, MONAView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID58771
KEGG Compound IDC13061
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound80641
PDB IDNot Available
ChEBI ID31169
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:15307787 ]
  2. 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. [PubMed:3811034 ]
  3. 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. [PubMed:6668314 ]
  4. 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. [PubMed:670346 ]