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Record Information
Version4.0
Creation Date2013-07-09 16:10:58 UTC
Update Date2017-09-27 08:43:58 UTC
HMDB IDHMDB0060984
Secondary Accession Numbers
  • HMDB60984
Metabolite Identification
Common Namedapsone hydroxylamine
Descriptiondapsone hydroxylamine is a metabolite of dapsone. Dapsone (diamino-diphenyl sulfone) is a medication most commonly used in combination with rifampicin and clofazimine as multidrug therapy (MDT) for the treatment of Mycobacterium leprae infections. It is also second-line treatment for prophylaxis (prevention) against Pneumocystis pneumonia (PCP) caused by Pneumocystis jirovecii (formerly P. carinii) in HIV patients in whom CD4 counts are below 200/mm. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
4-amino-4'-HydroxylaminodiphenylsulfoneMeSH
4-amino-4'-Hydroxylaminodiphenylsulfone, T-labeled CPDMeSH
4-hydroxylamino-4'-Aminophenyl sulfoneMeSH
N-HydroxydapsoneMeSH
DDS-NOHMeSH
HADSMeSH
Chemical FormulaC12H12N2O3S
Average Molecular Weight264.3
Monoisotopic Molecular Weight264.05686295
IUPAC Name4-[4-(hydroxyamino)benzenesulfonyl]aniline
Traditional Name4-[4-(hydroxyamino)benzenesulfonyl]aniline
CAS Registry NumberNot Available
SMILES
NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NO)C=C1
InChI Identifier
InChI=1S/C12H12N2O3S/c13-9-1-5-11(6-2-9)18(16,17)12-7-3-10(14-15)4-8-12/h1-8,14-15H,13H2
InChI KeyIYDSJDWESCGRKW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzenesulfonyl compounds
Alternative Parents
Substituents
  • Benzenesulfonyl group
  • N-phenylhydroxylamine
  • 1-hydroxylamino, 2-unsubstituted benzenoid
  • Arylhydroxamate
  • Aniline or substituted anilines
  • Primary aromatic amine
  • Sulfone
  • Sulfonyl
  • N-organohydroxylamine
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
logP0.89ALOGPS
logP1.61ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)13.03ChemAxon
pKa (Strongest Basic)3.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.28 m³·mol⁻¹ChemAxon
Polarizability26.32 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2930000000-963db6335e517b89cb9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0090000000-eddce420891c2cee706fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ls-1090000000-8d51583ba3d5d8383156View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvl-9300000000-017a704e155958170002View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-2a5f29cb14095d7f8711View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0290000000-0e07acf82ab3bd4b0128View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9700000000-2b318a7d7f05b49e79f3View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00301
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound65387
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available