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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2019-01-11 19:35:24 UTC
HMDB IDHMDB0015276
Secondary Accession Numbers
  • HMDB15276
Metabolite Identification
Common NameSulfoxone
DescriptionSulfoxone is only found in individuals that have used or taken this drug. It is a water-soluble sulfone used as an antileprosy drug. It has been used with limited success in the treatment of dermatitis herpetiformis. Sulfoxone is a competitive inhibitor of bacterial enzyme dihydropteroate synthetase. The normal substrate for the enzyme, para-aminobenzoic acid (PABA) cannot bind as usual. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Structure
Data?1547235324
Synonyms
ValueSource
Sodium aldesulphoneHMDB
Sodium sulfoxoneHMDB
DiasoneMeSH
Sulfoxone sodiumMeSH
Aldesulfon sodiumMeSH
Sulfoxone, disodium saltMeSH
Chemical FormulaC14H16N2O6S3
Average Molecular Weight404.482
Monoisotopic Molecular Weight404.017048324
IUPAC Name[(4-{4-[(sulfinomethyl)amino]benzenesulfonyl}phenyl)amino]methanesulfinic acid
Traditional Namesulfoxone
CAS Registry Number144-75-2
SMILES
OS(=O)CNC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NCS(O)=O)C=C1
InChI Identifier
InChI=1S/C14H16N2O6S3/c17-23(18)9-15-11-1-5-13(6-2-11)25(21,22)14-7-3-12(4-8-14)16-10-24(19)20/h1-8,15-16H,9-10H2,(H,17,18)(H,19,20)
InChI KeyNEDPPCHNEOMTJV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonyl compounds
Direct ParentBenzenesulfonyl compounds
Alternative Parents
Substituents
  • Benzenesulfonyl group
  • Phenylalkylamine
  • Secondary aliphatic/aromatic amine
  • Sulfinic acid
  • Sulfone
  • Sulfonyl
  • Alkanesulfinic acid
  • Alkanesulfinic acid or derivatives
  • Sulfinic acid derivative
  • Secondary amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.63 g/LNot Available
LogP-2.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.63 g/LALOGPS
logP1.38ALOGPS
logP-1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
pKa (Strongest Basic)-0.056ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.8 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity96.95 m³·mol⁻¹ChemAxon
Polarizability38.81 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0942000000-fa144ba1d91da00af91aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0002900000-b79ac654dccbe6452a6dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-2139100000-282920b406e9a1d6fec7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c04-4952000000-0f1951a3a6edae661ff2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-9013500000-8e2e9c226813b184bbfbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9001000000-63863cc52af9ddaa21ceJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9200000000-6aaeba4f6749f08ec307JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01145 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01145 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01145
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5158
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfoxone
METLIN IDNot Available
PubChem Compound5351
PDB IDNot Available
ChEBI ID553043
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available