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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:49:52 UTC
Update Date2021-09-14 15:47:16 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 belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring. Carboxybupranolol, 4-chloro-3-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. Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid is a very strong basic compound (based on its pKa). Its potency is similar to propranolol.
Structure
Data?1563866149
Synonyms
ValueSource
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoateGenerator
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
Description Belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+169.0430932474
DeepCCS[M-H]-166.68230932474
DeepCCS[M-2H]-199.56830932474
DeepCCS[M+Na]+175.13430932474
AllCCS[M+H]+167.932859911
AllCCS[M+H-H2O]+164.932859911
AllCCS[M+NH4]+170.732859911
AllCCS[M+Na]+171.532859911
AllCCS[M-H]-168.932859911
AllCCS[M+Na-2H]-169.532859911
AllCCS[M+HCOO]-170.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acidCCCCNCC(O)COC1=C(Cl)C=CC(=C1)C(O)=O3966.1Standard polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acidCCCCNCC(O)COC1=C(Cl)C=CC(=C1)C(O)=O2448.6Standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acidCCCCNCC(O)COC1=C(Cl)C=CC(=C1)C(O)=O2437.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,1TMS,isomer #1CCCCNCC(COC1=CC(C(=O)O)=CC=C1Cl)O[Si](C)(C)C2473.0Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,1TMS,isomer #2CCCCNCC(O)COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1Cl2457.4Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,1TMS,isomer #3CCCCN(CC(O)COC1=CC(C(=O)O)=CC=C1Cl)[Si](C)(C)C2552.7Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,2TMS,isomer #1CCCCNCC(COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1Cl)O[Si](C)(C)C2410.8Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,2TMS,isomer #2CCCCN(CC(COC1=CC(C(=O)O)=CC=C1Cl)O[Si](C)(C)C)[Si](C)(C)C2556.2Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,2TMS,isomer #3CCCCN(CC(O)COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1Cl)[Si](C)(C)C2494.6Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,3TMS,isomer #1CCCCN(CC(COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1Cl)O[Si](C)(C)C)[Si](C)(C)C2506.7Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,3TMS,isomer #1CCCCN(CC(COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1Cl)O[Si](C)(C)C)[Si](C)(C)C2538.9Standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,3TMS,isomer #1CCCCN(CC(COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1Cl)O[Si](C)(C)C)[Si](C)(C)C2762.1Standard polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,1TBDMS,isomer #1CCCCNCC(COC1=CC(C(=O)O)=CC=C1Cl)O[Si](C)(C)C(C)(C)C2720.4Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,1TBDMS,isomer #2CCCCNCC(O)COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1Cl2719.6Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,1TBDMS,isomer #3CCCCN(CC(O)COC1=CC(C(=O)O)=CC=C1Cl)[Si](C)(C)C(C)(C)C2807.1Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,2TBDMS,isomer #1CCCCNCC(COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1Cl)O[Si](C)(C)C(C)(C)C2903.0Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,2TBDMS,isomer #2CCCCN(CC(COC1=CC(C(=O)O)=CC=C1Cl)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3052.4Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,2TBDMS,isomer #3CCCCN(CC(O)COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1Cl)[Si](C)(C)C(C)(C)C3012.0Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,3TBDMS,isomer #1CCCCN(CC(COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1Cl)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3255.3Semi standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,3TBDMS,isomer #1CCCCN(CC(COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1Cl)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3078.4Standard non polar33892256
Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid,3TBDMS,isomer #1CCCCN(CC(COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1Cl)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3046.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0089-9630000000-5acd659769505b50a3532017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0fgc-9251200000-ba2aedde7c5361eb1ba62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 10V, Positive-QTOFsplash10-0kai-4296000000-168b0a1b61e852d2e26c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 20V, Positive-QTOFsplash10-0a4i-9350000000-5c4f054fe03e360550272017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 40V, Positive-QTOFsplash10-0a4i-9200000000-10ea4f318bd02cf399762017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 10V, Negative-QTOFsplash10-0uk9-1549000000-5f1b5c63e43f48fd8b492017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 20V, Negative-QTOFsplash10-00fr-1900000000-c5cbe90e7ce3f7ceb3142017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 40V, Negative-QTOFsplash10-004i-0900000000-00e398941dbf2b0649cd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 10V, Positive-QTOFsplash10-0udi-0129000000-45f0ecec6a1e358fd7062021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 20V, Positive-QTOFsplash10-0w9r-2942000000-28c4e49cb962fb8a42a32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 40V, Positive-QTOFsplash10-0fk9-5910000000-c09745774f43bcfcee022021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 10V, Negative-QTOFsplash10-0udi-0319000000-c973e865a6519ba5c5cf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 20V, Negative-QTOFsplash10-004i-0900000000-8079a8206472f73fc73a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid 40V, Negative-QTOFsplash10-004i-2900000000-a038017076ac7a73c8382021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound180626
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available