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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:50 UTC
HMDB IDHMDB0015028
Secondary Accession Numbers
  • HMDB15028
Metabolite Identification
Common NameSulfapyridine
DescriptionSulfapyridine is only found in individuals that have used or taken this drug. It is an antibacterial, potentially toxic, used to treat certain skin diseases. [PubChem] Sulfapyridine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid by means of processing the substrate para-aminobenzoic acid (PABA). Dihydropteroate synthetase activity is vital in the synthesis of folate, and folate is required for cells to make nucleic acids, such as DNA or RNA. So if DNA molecules cannot be built, the cell cannot divide.
Structure
Data?1582753249
Synonyms
ValueSource
2-(p-Aminobenzenesulphonamido)pyridineChEBI
2-SulfanilamidopyridinChEBI
2-SulfanilamidopyridineChEBI
2-SulfanilylaminopyridineChEBI
2-SulfapyridineChEBI
4-(2-Pyridinylsulfonyl)anilineChEBI
4-[(2-Pyridylamino)sulfonyl]anilineChEBI
4-Amino-N,2-pyridinylbenzenesulfonamideChEBI
4-Amino-N-pyridin-2-yl-benzenesulfonamideChEBI
N-2-PyridylsulfanilamideChEBI
N(1)-2-PyridylsulfanilamideChEBI
N(1)-PyridylsulfanilamideChEBI
SolfapiridinaChEBI
SulfapiridinaChEBI
SulfapyridinumChEBI
SulphapyridineChEBI
2-(p-Aminobenzenesulfonamido)pyridineGenerator
2-SulphanilamidopyridinGenerator
2-SulphanilamidopyridineGenerator
2-SulphanilylaminopyridineGenerator
2-SulphapyridineGenerator
4-(2-Pyridinylsulphonyl)anilineGenerator
4-[(2-Pyridylamino)sulphonyl]anilineGenerator
4-Amino-N,2-pyridinylbenzenesulphonamideGenerator
4-Amino-N-pyridin-2-yl-benzenesulphonamideGenerator
N-2-PyridylsulphanilamideGenerator
N(1)-2-PyridylsulphanilamideGenerator
N(1)-PyridylsulphanilamideGenerator
SulphapiridinaGenerator
SulphapyridinumGenerator
N1-2-PyridylsulfanilamideHMDB
SulphapyridinHMDB
Chemical FormulaC11H11N3O2S
Average Molecular Weight249.289
Monoisotopic Molecular Weight249.057197301
IUPAC Name4-amino-N-(pyridin-2-yl)benzene-1-sulfonamide
Traditional Nameronin
CAS Registry Number144-83-2
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=CC=N1
InChI Identifier
InChI=1S/C11H11N3O2S/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11/h1-8H,12H2,(H,13,14)
InChI KeyGECHUMIMRBOMGK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Pyridine
  • Organosulfonic acid amide
  • Imidolactam
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Primary amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point192 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.24 g/LNot Available
LogP0.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM150.830932474
[M+H]+Not Available151.591http://allccs.zhulab.cn/database/detail?ID=AllCCS00000818
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP0.84ALOGPS
logP1.01ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.24ChemAxon
pKa (Strongest Basic)2.63ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.08 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.75 m³·mol⁻¹ChemAxon
Polarizability24.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.52531661259
DarkChem[M-H]-158.03731661259
DeepCCS[M+H]+154.87230932474
DeepCCS[M-H]-152.51430932474
DeepCCS[M-2H]-185.48530932474
DeepCCS[M+Na]+160.96530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfapyridineNC1=CC=C(C=C1)S(=O)(=O)NC1=CC=CC=N13990.5Standard polar33892256
SulfapyridineNC1=CC=C(C=C1)S(=O)(=O)NC1=CC=CC=N12578.5Standard non polar33892256
SulfapyridineNC1=CC=C(C=C1)S(=O)(=O)NC1=CC=CC=N12483.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfapyridine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C12632.8Semi standard non polar33892256
Sulfapyridine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C12439.6Standard non polar33892256
Sulfapyridine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C13411.1Standard polar33892256
Sulfapyridine,1TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=N1)S(=O)(=O)C1=CC=C(N)C=C12468.6Semi standard non polar33892256
Sulfapyridine,1TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=N1)S(=O)(=O)C1=CC=C(N)C=C12399.4Standard non polar33892256
Sulfapyridine,1TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=N1)S(=O)(=O)C1=CC=C(N)C=C13582.6Standard polar33892256
Sulfapyridine,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C1)[Si](C)(C)C2506.2Semi standard non polar33892256
Sulfapyridine,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C1)[Si](C)(C)C2516.1Standard non polar33892256
Sulfapyridine,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C1)[Si](C)(C)C3272.4Standard polar33892256
Sulfapyridine,2TMS,isomer #2C[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C)C=C12486.4Semi standard non polar33892256
Sulfapyridine,2TMS,isomer #2C[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C)C=C12500.6Standard non polar33892256
Sulfapyridine,2TMS,isomer #2C[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C)C=C13129.4Standard polar33892256
Sulfapyridine,3TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C)C=C1)[Si](C)(C)C2402.7Semi standard non polar33892256
Sulfapyridine,3TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C)C=C1)[Si](C)(C)C2594.1Standard non polar33892256
Sulfapyridine,3TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C)C=C1)[Si](C)(C)C3017.4Standard polar33892256
Sulfapyridine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C12862.1Semi standard non polar33892256
Sulfapyridine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C12672.6Standard non polar33892256
Sulfapyridine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C13484.1Standard polar33892256
Sulfapyridine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=N1)S(=O)(=O)C1=CC=C(N)C=C12694.7Semi standard non polar33892256
Sulfapyridine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=N1)S(=O)(=O)C1=CC=C(N)C=C12617.7Standard non polar33892256
Sulfapyridine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=N1)S(=O)(=O)C1=CC=C(N)C=C13574.3Standard polar33892256
Sulfapyridine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C1)[Si](C)(C)C(C)(C)C2998.4Semi standard non polar33892256
Sulfapyridine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C1)[Si](C)(C)C(C)(C)C2943.3Standard non polar33892256
Sulfapyridine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=CC=N2)C=C1)[Si](C)(C)C(C)(C)C3313.4Standard polar33892256
Sulfapyridine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C=C12911.4Semi standard non polar33892256
Sulfapyridine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C=C12939.3Standard non polar33892256
Sulfapyridine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C=C13247.3Standard polar33892256
Sulfapyridine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3102.1Semi standard non polar33892256
Sulfapyridine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3242.3Standard non polar33892256
Sulfapyridine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3186.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Sulfapyridine CI-B (Non-derivatized)splash10-0udi-0090000000-6205fa17064877bf03df2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sulfapyridine CI-B (Non-derivatized)splash10-0udi-0090000000-6205fa17064877bf03df2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfapyridine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0537-9230000000-93117665cf41b575fe9d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfapyridine 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 - Sulfapyridine LC-ESI-qTof , Positive-QTOFsplash10-0a59-4900000000-27a3388f44d41a748f992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-QTOF , positive-QTOFsplash10-0a59-4920000000-ddd28eca3499faaddfb12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0900000000-76404b7958aaaddb00c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-b794dcd70eedfd04a9e82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0udi-1690000000-d32f010faae95dd6e5dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-3900000000-b89b3d587bf8893e343a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0a4l-7900000000-e9c1ce1a2bfb8587016b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-052f-9600000000-c2b3b96e2d3db5fc940f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-05mo-9400000000-6eeb6714b222ec20731e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-14bd7d3423dbbc1677f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0udi-1690000000-ec5ad1677ec436c150762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-3900000000-3221fbcec55c511e58a02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-7900000000-4959721f5e57ee1708c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-052f-9600000000-cb7f712bbbba5e75ed732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-05mo-9400000000-542a7f83b7c124aeaa3b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0a59-0900000000-ebce9cc4e8380518ddec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0a4l-5900000000-c36697c8e5b4522ccfc52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-052f-9600000000-07faf61cc06e82c703a62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfapyridine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0900000000-2ae47a77fd32fcf2200e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfapyridine 10V, Positive-QTOFsplash10-0udi-0290000000-80dcb81e6cfe7634d7eb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfapyridine 20V, Positive-QTOFsplash10-0a4i-4940000000-e88afb3731cf854038552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfapyridine 40V, Positive-QTOFsplash10-00mk-9000000000-8d55b897022b24c135b52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfapyridine 10V, Negative-QTOFsplash10-0002-0090000000-f9fc95635e84b684e50e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfapyridine 20V, Negative-QTOFsplash10-0002-2290000000-25d1c1c63465ef46b4342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfapyridine 40V, Negative-QTOFsplash10-0006-9200000000-528bf1a0d311cecb47b62016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00891 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00891 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00891
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5145
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfapyridine
METLIN IDNot Available
PubChem Compound5336
PDB IDNot Available
ChEBI ID132842
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]