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Record Information
Version3.6
Creation Date2013-07-04 18:57:52 UTC
Update Date2016-02-11 08:12:27 UTC
HMDB IDHMDB60761
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Chloro-5-sulfamoylanthranilic acid
Description4-Chloro-5-sulfamoylanthranilic acid is a metabolite of furosemide. Furosemide or frusemide is a loop diuretic used in the treatment of congestive heart failure and edema. It is most commonly marketed by Sanofi-Aventis under the brand name Lasix. It has also been used to prevent Thoroughbred and Standardbred race horses from bleeding through the nose during races. Along with some other diuretics, furosemide is also included on the World Anti-Doping Agency's banned drug list due to its alleged use as a masking agent for other drugs. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC7H7ClN2O4S
Average Molecular Weight250.659
Monoisotopic Molecular Weight249.981505119
IUPAC Name2-amino-4-chloro-5-sulfamoylbenzoic acid
Traditional Name2-amino-4-chloro-5-sulfamoylbenzoic acid
CAS Registry Number3086-91-7
SMILES
NC1=CC(Cl)=C(C=C1C(O)=O)S(N)(=O)=O
InChI Identifier
InChI=1S/C7H7ClN2O4S/c8-4-2-5(9)3(7(11)12)1-6(4)15(10,13)14/h1-2H,9H2,(H,11,12)(H2,10,13,14)
InChI KeyInChIKey=QQLJBZFXGDHSRU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Halobenzoic acid
  • 4-halobenzoic acid
  • 4-halobenzoic acid or derivatives
  • Sulfonylaniline
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoic acid or derivatives
  • Substituted aniline
  • Benzoyl
  • Halobenzene
  • Chlorobenzene
  • Aniline
  • Primary aromatic amine
  • Aryl halide
  • Aryl chloride
  • Vinylogous amide
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • 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 Solubility2.99 mg/mLALOGPS
logP0.92ALOGPS
logP0.66ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-0.27ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area123.48 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.98 m3·mol-1ChemAxon
Polarizability21.28 Å3ChemAxon
Number of Rings1ChemAxon
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 IDDBMET00729
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 LinkHMDB60761
Metagene LinkHMDB60761
METLIN IDNot Available
PubChem Compound76523
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available