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
StatusExpected but not Quantified
Creation Date2013-07-22 19:49:52 UTC
Update Date2017-12-07 18:54:48 UTC
HMDB IDHMDB0061131
Secondary Accession Numbers
  • HMDB61131
Metabolite Identification
Common NameCarboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid
DescriptionCarboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid is a metabolite of bupranolol. Bupranolol is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. Its potency is similar to propranolol. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC14H20ClNO4
Average Molecular Weight301.766
Monoisotopic Molecular Weight301.10808584
IUPAC Name3-[3-(butylamino)-2-hydroxypropoxy]-4-chlorobenzoic acid
Traditional Name3-[3-(butylamino)-2-hydroxypropoxy]-4-chlorobenzoic acid
CAS Registry NumberNot Available
SMILES
CCCCNCC(O)COC1=C(Cl)C=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C14H20ClNO4/c1-2-3-6-16-8-11(17)9-20-13-7-10(14(18)19)4-5-12(13)15/h4-5,7,11,16-17H,2-3,6,8-9H2,1H3,(H,18,19)
InChI KeyIZPPAHZRVDTEHO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentHalobenzoic acids
Alternative Parents
Substituents
  • 4-halobenzoic acid or derivatives
  • 4-halobenzoic acid
  • Halobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Amino acid
  • Secondary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic nitrogen compound
  • Organochloride
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Amine
  • Organooxygen compound
  • Organic oxygen compound
  • Organohalogen compound
  • 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 Solubility0.13 g/LALOGPS
logP0.35ALOGPS
logP-0.066ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.79 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity77.14 m³·mol⁻¹ChemAxon
Polarizability32.09 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, Positivesplash10-0089-9630000000-5acd659769505b50a353View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fgc-9251200000-ba2aedde7c5361eb1ba6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kai-4296000000-168b0a1b61e852d2e26cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9350000000-5c4f054fe03e36055027View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-10ea4f318bd02cf39976View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-1549000000-5f1b5c63e43f48fd8b49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-1900000000-c5cbe90e7ce3f7ceb314View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-00e398941dbf2b0649cdView 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
      DrugBank Metabolite IDDBMET00809
      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 CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available