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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015412
Secondary Accession Numbers
  • HMDB15412
Metabolite Identification
Common NameSulfacytine
DescriptionSulfacytine is a short-acting sulfonamide. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Sulfacytine is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Structure
Data?1582753294
Synonyms
ValueSource
RenoquidKegg
SulphacytineGenerator
1-Ethyl N4-sulfanilylcytosinHMDB
1-Ethyl-N-sulfanilylcytosineHMDB
N-Sulfanilyl-L-ethylcytosineHMDB
N(1)-(1-Ethyl-1,2-dihydro-2-oxo-4-pyrimidinyl)sulfanilamideHMDB
Chemical FormulaC12H14N4O3S
Average Molecular Weight294.33
Monoisotopic Molecular Weight294.078661024
IUPAC Name4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide
Traditional Namesulfacytine
CAS Registry Number17784-12-2
SMILES
CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O
InChI Identifier
InChI=1S/C12H14N4O3S/c1-2-16-8-7-11(14-12(16)17)15-20(18,19)10-5-3-9(13)4-6-10/h3-8H,2,13H2,1H3,(H,14,15,17)
InChI KeySIBQAECNSSQUOD-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
  • Pyrimidone
  • Hydropyrimidine
  • Pyrimidine
  • Organosulfonic acid amide
  • Imidolactam
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point166.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.47 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP0.51ALOGPS
logP0.055ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.55ChemAxon
pKa (Strongest Basic)2.17ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.86 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity75.49 m³·mol⁻¹ChemAxon
Polarizability29.43 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]+168.01731661259
DarkChem[M-H]-169.0131661259
DeepCCS[M+H]+167.8330932474
DeepCCS[M-H]-165.47230932474
DeepCCS[M-2H]-198.35830932474
DeepCCS[M+Na]+173.92330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfacytineCCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O4573.6Standard polar33892256
SulfacytineCCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O2946.3Standard non polar33892256
SulfacytineCCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O3106.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfacytine,1TMS,isomer #1CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O3095.0Semi standard non polar33892256
Sulfacytine,1TMS,isomer #1CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O2839.4Standard non polar33892256
Sulfacytine,1TMS,isomer #1CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O4028.7Standard polar33892256
Sulfacytine,1TMS,isomer #2CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O2793.4Semi standard non polar33892256
Sulfacytine,1TMS,isomer #2CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O2740.2Standard non polar33892256
Sulfacytine,1TMS,isomer #2CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O4189.5Standard polar33892256
Sulfacytine,2TMS,isomer #1CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O2851.7Semi standard non polar33892256
Sulfacytine,2TMS,isomer #1CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O2872.8Standard non polar33892256
Sulfacytine,2TMS,isomer #1CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O3672.0Standard polar33892256
Sulfacytine,2TMS,isomer #2CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O2865.2Semi standard non polar33892256
Sulfacytine,2TMS,isomer #2CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O2898.6Standard non polar33892256
Sulfacytine,2TMS,isomer #2CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O3775.2Standard polar33892256
Sulfacytine,3TMS,isomer #1CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O2735.0Semi standard non polar33892256
Sulfacytine,3TMS,isomer #1CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O2957.1Standard non polar33892256
Sulfacytine,3TMS,isomer #1CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O3475.2Standard polar33892256
Sulfacytine,1TBDMS,isomer #1CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3341.2Semi standard non polar33892256
Sulfacytine,1TBDMS,isomer #1CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3047.6Standard non polar33892256
Sulfacytine,1TBDMS,isomer #1CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O4033.0Standard polar33892256
Sulfacytine,1TBDMS,isomer #2CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O3094.6Semi standard non polar33892256
Sulfacytine,1TBDMS,isomer #2CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O2971.0Standard non polar33892256
Sulfacytine,1TBDMS,isomer #2CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O4175.3Standard polar33892256
Sulfacytine,2TBDMS,isomer #1CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3319.1Semi standard non polar33892256
Sulfacytine,2TBDMS,isomer #1CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3318.1Standard non polar33892256
Sulfacytine,2TBDMS,isomer #1CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3723.9Standard polar33892256
Sulfacytine,2TBDMS,isomer #2CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3392.4Semi standard non polar33892256
Sulfacytine,2TBDMS,isomer #2CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3330.4Standard non polar33892256
Sulfacytine,2TBDMS,isomer #2CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3770.4Standard polar33892256
Sulfacytine,3TBDMS,isomer #1CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3468.3Semi standard non polar33892256
Sulfacytine,3TBDMS,isomer #1CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3615.8Standard non polar33892256
Sulfacytine,3TBDMS,isomer #1CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O3610.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulfacytine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0699-5970000000-fcf781e9c8d92fac41fe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfacytine 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 - Sulfacytine 10V, Positive-QTOFsplash10-002b-0490000000-f5ef4a3fc969278d52f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 20V, Positive-QTOFsplash10-0ab9-1930000000-cca50de9df755740762c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 40V, Positive-QTOFsplash10-0gb9-9100000000-0e0f88d63239781bb3dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 10V, Negative-QTOFsplash10-0006-0190000000-5678559deb4df7cd70e52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 20V, Negative-QTOFsplash10-0zml-1590000000-f8b5e6818df98f145ac82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 40V, Negative-QTOFsplash10-05bf-9710000000-fe4bdffade8dc1239d0f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 10V, Positive-QTOFsplash10-052b-0790000000-858e661c23fea2a281ef2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 20V, Positive-QTOFsplash10-0005-1950000000-8efb821459dc738d0bc62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 40V, Positive-QTOFsplash10-0006-9310000000-af522fa67546c379ca392021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 10V, Negative-QTOFsplash10-0006-0290000000-14fefa164bb613784c582021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 20V, Negative-QTOFsplash10-00dm-0920000000-252f3b6dbf3bb165dace2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfacytine 40V, Negative-QTOFsplash10-052f-6900000000-bc74a22245fbb377bce22021-10-11Wishart 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 DB01298 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01298 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01298
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5131
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfacytine
METLIN IDNot Available
PubChem Compound5322
PDB IDNot Available
ChEBI ID775007
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