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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 UTC
HMDB IDHMDB0014802
Secondary Accession Numbers
  • HMDB14802
Metabolite Identification
Common NameSulfametopyrazine
DescriptionSulfametopyrazine is only found in individuals that have used or taken this drug. It is a long-acting plasma-bound sulfonamide used for respiratory and urinary tract infections and also for malaria. [PubChem]Sulfametopyrazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. Para-aminobenzoic acid (PABA), a substrate of the enzyme is prevented from binding. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Structure
Data?1582753222
Synonyms
ValueSource
SulfaleneKegg
SulfamethopyrazineKegg
KelfizinaKegg
SulphaleneGenerator
SulphamethopyrazineGenerator
SulphametopyrazineGenerator
Pharmacia brand OF sulfaleneHMDB
SulfapyrazinmethoxineHMDB
LongumHMDB
SulfamethoxypyrazineHMDB
KelfizineHMDB
SulfametopyrazineMeSH
Chemical FormulaC11H12N4O3S
Average Molecular Weight280.303
Monoisotopic Molecular Weight280.06301096
IUPAC Name4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide
Traditional Namelongum
CAS Registry Number152-47-6
SMILES
COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1
InChI Identifier
InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)
InChI KeyKXRZBTAEDBELFD-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
  • Methoxypyrazine
  • Aniline or substituted anilines
  • Alkyl aryl ether
  • Pyrazine
  • Imidolactam
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Azacycle
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point169.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.41 g/LNot Available
LogP0.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP0.41ALOGPS
logP0.23ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)5.91ChemAxon
pKa (Strongest Basic)1.98ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.2 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity70.37 m³·mol⁻¹ChemAxon
Polarizability27.12 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]+162.74231661259
DarkChem[M-H]-163.43331661259
DeepCCS[M+H]+164.79830932474
DeepCCS[M-H]-162.4430932474
DeepCCS[M-2H]-195.33230932474
DeepCCS[M+Na]+170.89130932474
AllCCS[M+H]+163.732859911
AllCCS[M+H-H2O]+160.132859911
AllCCS[M+NH4]+167.132859911
AllCCS[M+Na]+168.032859911
AllCCS[M-H]-159.532859911
AllCCS[M+Na-2H]-159.432859911
AllCCS[M+HCOO]-159.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfametopyrazineCOC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C14065.1Standard polar33892256
SulfametopyrazineCOC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C12698.4Standard non polar33892256
SulfametopyrazineCOC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C12569.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfametopyrazine,1TMS,isomer #1COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C12847.7Semi standard non polar33892256
Sulfametopyrazine,1TMS,isomer #1COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C12589.5Standard non polar33892256
Sulfametopyrazine,1TMS,isomer #1COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C14196.7Standard polar33892256
Sulfametopyrazine,1TMS,isomer #2COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C12595.6Semi standard non polar33892256
Sulfametopyrazine,1TMS,isomer #2COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C12523.9Standard non polar33892256
Sulfametopyrazine,1TMS,isomer #2COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C14173.3Standard polar33892256
Sulfametopyrazine,2TMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C12669.2Semi standard non polar33892256
Sulfametopyrazine,2TMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C12634.6Standard non polar33892256
Sulfametopyrazine,2TMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C13651.5Standard polar33892256
Sulfametopyrazine,2TMS,isomer #2COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C12687.7Semi standard non polar33892256
Sulfametopyrazine,2TMS,isomer #2COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C12669.7Standard non polar33892256
Sulfametopyrazine,2TMS,isomer #2COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C13974.6Standard polar33892256
Sulfametopyrazine,3TMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C12590.6Semi standard non polar33892256
Sulfametopyrazine,3TMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C12756.9Standard non polar33892256
Sulfametopyrazine,3TMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C13450.3Standard polar33892256
Sulfametopyrazine,1TBDMS,isomer #1COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C13081.9Semi standard non polar33892256
Sulfametopyrazine,1TBDMS,isomer #1COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C12813.4Standard non polar33892256
Sulfametopyrazine,1TBDMS,isomer #1COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C14212.9Standard polar33892256
Sulfametopyrazine,1TBDMS,isomer #2COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C12848.8Semi standard non polar33892256
Sulfametopyrazine,1TBDMS,isomer #2COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C12737.8Standard non polar33892256
Sulfametopyrazine,1TBDMS,isomer #2COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C14131.9Standard polar33892256
Sulfametopyrazine,2TBDMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C13094.2Semi standard non polar33892256
Sulfametopyrazine,2TBDMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C13092.9Standard non polar33892256
Sulfametopyrazine,2TBDMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C13688.5Standard polar33892256
Sulfametopyrazine,2TBDMS,isomer #2COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13162.6Semi standard non polar33892256
Sulfametopyrazine,2TBDMS,isomer #2COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13094.1Standard non polar33892256
Sulfametopyrazine,2TBDMS,isomer #2COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13957.8Standard polar33892256
Sulfametopyrazine,3TBDMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13232.3Semi standard non polar33892256
Sulfametopyrazine,3TBDMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13451.9Standard non polar33892256
Sulfametopyrazine,3TBDMS,isomer #1COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13560.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulfametopyrazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ec-8950000000-e07820181c0d509b67442017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfametopyrazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 10V, Positive-QTOFsplash10-001i-0390000000-901e323a546e976e468e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 20V, Positive-QTOFsplash10-0a4i-1930000000-14c0572c4c8b184323b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 40V, Positive-QTOFsplash10-0006-9100000000-a03460e59f372cc5cc792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 10V, Negative-QTOFsplash10-004i-0090000000-f18189296f030c2007f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 20V, Negative-QTOFsplash10-0a6r-9270000000-122f98f83af5be9e3a362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 40V, Negative-QTOFsplash10-0006-9510000000-25323d1786b9b00afa092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 10V, Positive-QTOFsplash10-001i-0090000000-3b2c30b44d481a3733fb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 20V, Positive-QTOFsplash10-0a4i-2900000000-89fba7919d1854eb9b3f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 40V, Positive-QTOFsplash10-014l-9300000000-3fc5a487e85969c7a3df2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 10V, Negative-QTOFsplash10-004i-0290000000-941b74251f448ece145c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 20V, Negative-QTOFsplash10-0a4i-2900000000-81a3b923ab8ab3af78902021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfametopyrazine 40V, Negative-QTOFsplash10-052f-6900000000-10bd0c8b52e73e20a8d82021-10-11Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00664 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00664 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00664
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8695
KEGG Compound IDC12616
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfalene
METLIN IDNot Available
PubChem Compound9047
PDB IDNot Available
ChEBI ID1049710
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 ReferencesNot Available