Showing metabocard for Dapsone (BMDB0062220)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-07-17 17:20:17 UTC
Update Date2020-04-22 15:51:38 UTC
BMDB IDBMDB0062220
Secondary Accession Numbers
  • BMDB62220
Metabolite Identification
Common NameDapsone
DescriptionDapsone, also known as diaphenylsulfone or 4,4'-dapsone, 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. Dapsone is a drug which is used for the treatment and management of leprosy and dermatitis herpetiformis. Based on a literature review a significant number of articles have been published on Dapsone.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1'-Sulfonylbis(4-aminobenzene)ChEBI
4,4'-DapsoneChEBI
4,4'-Diaminodiphenyl sulfoneChEBI
4,4'-SulfonylbisanilineChEBI
4,4'-SulfonylbisbenzenamineChEBI
4-(4-Amino-benzenesulfonyl)-phenylamineChEBI
4-(4-Aminophenylsulfonyl)anilineChEBI
4-(4-Aminophenylsulfonyl)benzenamineChEBI
4-Aminophenyl sulfoneChEBI
Bis(4-aminophenyl)sulfoneChEBI
Bis(p-aminophenyl) sulfoneChEBI
DADPSChEBI
DapsonaChEBI
DapsonumChEBI
DDSChEBI
DIAPHENYLsulfoneChEBI
p,P'-diaminodiphenyl sulfoneChEBI
p,p-SulphonylbisbenzamineChEBI
p,p-SulphonylbisbenzenamineChEBI
p-Aminophenyl sulfoneChEBI
AczoneKegg
1,1'-Sulphonylbis(4-aminobenzene)Generator
4,4'-Diaminodiphenyl sulphoneGenerator
4,4'-SulphonylbisanilineGenerator
4,4'-SulphonylbisbenzenamineGenerator
4-(4-Amino-benzenesulphonyl)-phenylamineGenerator
4-(4-Aminophenylsulphonyl)anilineGenerator
4-(4-Aminophenylsulphonyl)benzenamineGenerator
4-Aminophenyl sulphoneGenerator
Bis(4-aminophenyl)sulphoneGenerator
Bis(p-aminophenyl) sulphoneGenerator
DIAPHENYLsulphoneGenerator
p,P'-diaminodiphenyl sulphoneGenerator
p,p-SulfonylbisbenzamineGenerator
p,p-SulfonylbisbenzenamineGenerator
p-Aminophenyl sulphoneGenerator
1,1'-Sulfonylbis[4-aminobenzene]HMDB
4,4'-DiaminodiphenylsulfoneHMDB
4,4'-SulfonylbisbenzeneamineHMDB
4,4'-SulfonyldianilinHMDB
4,4'-SulfonyldianilineHMDB
DDS, PharmaceuticalHMDB
Mex-america brand OF dapsoneHMDB
SulfonaHMDB
4,4' Diaminophenyl sulfoneHMDB
4,4'-Diaminophenyl sulfoneHMDB
Dapson-fatolHMDB
DisuloneHMDB
Fatol brand OF dapsoneHMDB
Orsade brand OF dapsoneHMDB
Sulfone, 4,4'-diaminophenylHMDB
SulfonyldianilineHMDB
AvlosulfoneHMDB
Dapsoderm-XHMDB
DiaminodiphenylsulfoneHMDB
Chemical FormulaC12H12N2O2S
Average Molecular Weight248.301
Monoisotopic Molecular Weight248.061948328
IUPAC Name4-(4-aminobenzenesulfonyl)aniline
Traditional Namedapsone
CAS Registry Number80-08-0
SMILES
NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C1
InChI Identifier
InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
InChI KeyMQJKPEGWNLWLTK-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Aniline or substituted anilines
  • Sulfonyl
  • Sulfone
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point175.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.84e-01 g/LNot Available
LogP0.4Not Available
Predicted Properties
PropertyValueSource
logP1.19ALOGPS
logP1.27ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)2.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.18 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.99 m³·mol⁻¹ChemAxon
Polarizability25.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0014395
DrugBank IDDB00250
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2849
KEGG Compound IDC07666
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDapsone
METLIN IDNot Available
PubChem Compound2955
PDB IDNot Available
ChEBI ID4325
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available