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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:57:52 UTC
Update Date2017-12-07 17:55:35 UTC
HMDB IDHMDB0060761
Secondary Accession Numbers
  • HMDB60761
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 KeyQQLJBZFXGDHSRU-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
  • Aminobenzoic acid
  • Aminobenzoic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • 4-halobenzoic acid
  • Halobenzoic acid
  • Benzenesulfonyl group
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Aniline or substituted anilines
  • Halobenzene
  • Chlorobenzene
  • Organosulfonic acid amide
  • Aryl halide
  • Aryl chloride
  • Vinylogous amide
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organochloride
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • 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 Solubility2.99 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.98 m³·mol⁻¹ChemAxon
Polarizability21.28 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-008i-7490000000-1a779a3f354541e00a68View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9082000000-ccec78c642d3aeb208d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-ee873faaac0c90b02940View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0190000000-9b12968207cf9f5960ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0930000000-c31bbd07e376696a52e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0090000000-fc900887e1e73eff1bd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-1f90643316c8b10d1dd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9230000000-beb365abda36ac404bc0View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
      Phenol Explorer Compound 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 Compound76523
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available