You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2013-07-09 16:11:05 UTC
Update Date2017-09-27 08:43:58 UTC
HMDB IDHMDB0060986
Secondary Accession Numbers
  • HMDB60986
Metabolite Identification
Common NameZafirlukast metabolite M5
DescriptionZafirlukast metabolite M5 is a metabolite of zafirlukast. Zafirlukast is an oral leukotriene receptor antagonist (LTRA) for the maintenance treatment of asthma, often used in conjunction with an inhaled steroid and/or long-acting bronchodilator. It is available as a tablet and is usually dosed twice daily. Another leukotriene receptor antagonist is montelukast (Singulair), taken once daily. Zileuton (Zyflo), also used in the treatment of asthma via its inhibition of 5-lipoxygenase, is taken four times per day. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC31H33N3O7S
Average Molecular Weight591.675
Monoisotopic Molecular Weight591.203921115
IUPAC Namecyclopentyl N-[1-(hydroxymethyl)-3-({2-methoxy-4-[(2-methylbenzenesulfonyl)carbamoyl]phenyl}methyl)-1H-indol-5-yl]carbamate
Traditional Namecyclopentyl N-[1-(hydroxymethyl)-3-({2-methoxy-4-[(2-methylbenzenesulfonyl)carbamoyl]phenyl}methyl)indol-5-yl]carbamate
CAS Registry NumberNot Available
SMILES
COC1=C(CC2=CN(CO)C3=C2C=C(NC(=O)OC2CCCC2)C=C3)C=CC(=C1)C(=O)NS(=O)(=O)C1=CC=CC=C1C
InChI Identifier
InChI=1S/C31H33N3O7S/c1-20-7-3-6-10-29(20)42(38,39)33-30(36)22-12-11-21(28(16-22)40-2)15-23-18-34(19-35)27-14-13-24(17-26(23)27)32-31(37)41-25-8-4-5-9-25/h3,6-7,10-14,16-18,25,35H,4-5,8-9,15,19H2,1-2H3,(H,32,37)(H,33,36)
InChI KeyHZAQOSFFIGVMDH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • 3-alkylindole
  • N-alkylindole
  • Benzenesulfonamide
  • Indole or derivatives
  • Indole
  • Benzenesulfonyl group
  • Benzoic acid or derivatives
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Phenoxy compound
  • Anisole
  • Alkyl aryl ether
  • Toluene
  • Substituted pyrrole
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Carbamic acid ester
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Pyrrole
  • Carbonic acid derivative
  • Alkanolamine
  • Carboxylic acid derivative
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.0018 g/LALOGPS
logP4.06ALOGPS
logP5.82ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.29ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area135.96 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity159.68 m³·mol⁻¹ChemAxon
Polarizability63.01 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
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-9303340000-ab8b3394c85292befd3fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-9101031000-bde32265b0d56db9dedbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-7100390000-bd1669339b6b49f3b570View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9003310000-57b04bc15ba931f3143cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9012200000-839e8ab30cffc35a3ee7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w2c-3100290000-81e701b4130112d0b043View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9502680000-f56485e7b67c844b10deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052v-9601300000-ea944d164e44905f56a4View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 IDDBMET00307
      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 Compound71549171
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available