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Record Information
Version3.6
Creation Date2013-07-09 16:11:05 UTC
Update Date2016-02-11 08:16:33 UTC
HMDB IDHMDB60986
Secondary Accession NumbersNone
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 KeyInChIKey=HZAQOSFFIGVMDH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Phenylcarbamate
  • Benzenesulfonamide
  • Indole or derivatives
  • Indole
  • Benzoic acid or derivatives
  • Benzamide
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Anisole
  • Toluene
  • Alkyl aryl ether
  • Substituted pyrrole
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Pyrrole
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Alkanolamine
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity159.68 m3·mol-1ChemAxon
Polarizability63.01 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 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
NuGOwiki LinkHMDB60986
Metagene LinkHMDB60986
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