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Record Information
Version3.6
Creation Date2013-07-22 19:52:40 UTC
Update Date2016-02-11 08:19:46 UTC
HMDB IDHMDB61176
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhenylacetic acid-N-isopropylnortropine-ester methobromide
DescriptionPhenylacetic acid-N-isopropylnortropine-ester methobromide is a metabolite of ipratropium bromide. Ipratropium bromide (trade names Atrovent, Apovent, and Aerovent) is an anticholinergic drug used for the treatment of chronic obstructive pulmonary disease and acute asthma. It blocks the muscarinic acetylcholine receptors in the smooth muscles of the bronchi in the lungs, opening the bronchi. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H34BrNO4
Average Molecular Weight516.467
Monoisotopic Molecular Weight515.167121228
IUPAC Name(1R,5R)-3-{[3-(benzoyloxy)-2-phenylpropanoyl]oxy}-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium bromide
Traditional Name(1R,5R)-3-{[3-(benzoyloxy)-2-phenylpropanoyl]oxy}-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium bromide
CAS Registry NumberNot Available
SMILES
[Br-].CC(C)[N+]1(C)[C@@H]2CC[C@@H]1CC(C2)OC(=O)C(COC(=O)C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C27H34NO4.BrH/c1-19(2)28(3)22-14-15-23(28)17-24(16-22)32-27(30)25(20-10-6-4-7-11-20)18-31-26(29)21-12-8-5-9-13-21;/h4-13,19,22-25H,14-18H2,1-3H3;1H/q+1;/p-1/t22-,23-,24?,25?,28?;/m1./s1
InChI KeyInChIKey=XHBYEUXSELWWNG-VHPVAZJWSA-M
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Phenylacetate
  • Benzoate ester
  • Tropane alkaloid
  • Benzylether
  • Benzoyl
  • N-alkylpyrrolidine
  • Piperidine
  • Dicarboxylic acid or derivatives
  • Quaternary ammonium salt
  • Pyrrolidine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic bromide salt
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • 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
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 Solubility6.24e-05 mg/mLALOGPS
logP1.6ALOGPS
logP0.68ChemAxon
logS-6.9ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity135.72 m3·mol-1ChemAxon
Polarizability28.43 Å3ChemAxon
Number of Rings4ChemAxon
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 IDDBMET00987
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 LinkHMDB61176
Metagene LinkHMDB61176
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available