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Record Information
Version3.6
Creation Date2013-07-09 16:10:58 UTC
Update Date2016-02-11 08:16:32 UTC
HMDB IDHMDB60984
Secondary Accession NumbersNone
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
SynonymsNot Available
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 KeyInChIKey=IYDSJDWESCGRKW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sulfonylanilines. These are compounds containing an aniline moiety which bears a sulfonyl group at ring position 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilines
Direct ParentSulfonylanilines
Alternative Parents
Substituents
  • Sulfonylaniline
  • Substituted aniline
  • Primary aromatic amine
  • Sulfonyl
  • Sulfone
  • N-organohydroxylamine
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.28 m3·mol-1ChemAxon
Polarizability26.32 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB60984
Metagene LinkHMDB60984
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