Human Metabolome Database Version 3.5

Showing metabocard for Propranolol (HMDB01849)

Record Information
Version 3.5
Creation Date 2006-02-16 02:05:30 -0700
Update Date 2013-02-08 17:10:51 -0700
HMDB ID HMDB01849
Secondary Accession Numbers None
Metabolite Identification
Common Name Propranolol
Description Propranolol is a widely used non-cardioselective beta-adrenergic antagonist. Propranolol is used in the treatment or prevention of many disorders including acute myocardial infarction, arrhythmias, angina pectoris, hypertension, hypertensive emergencies, hyperthyroidism, migraine, pheochromocytoma, menopause, and anxiety. --PubChem; Propranolol is a highly lipophilic drug achieving high concentrations in the brain. The duration of action of a single oral dose is longer than the half-life indicates and may be up to 12 hours, if the single dose is high enough (e.g. 80 mg). Effective plasma concentrations are between 10-100 ng/mL. -- Wikipedia; It was the first successful beta blocker developed. Propranolol is commonly marketed by Wyeth under the trade name Inderal.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. b-Propranolol
  2. beta-Propranolol
  3. Dociton
  4. Euprovasin
  5. Propanalol
  6. Propanix
  7. Propanolol
  8. Propranololo
Chemical Formula C16H21NO2
Average Molecular Weight 259.3434
Monoisotopic Molecular Weight 259.157228921
IUPAC Name [2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine
Traditional IUPAC Name propranolol
CAS Registry Number 525-66-6
SMILES CC(C)NCC(O)COC1=CC=CC2=CC=CC=C12
InChI Identifier InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3
InChI Key AQHHHDLHHXJYJD-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Acenes
Sub Class Naphthalenes
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • propanolamine(ChEBI)
  • secondary amine(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Alkyl Aryl Ether
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Naphthalenes
Ontology
Status Detected and Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 96 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.0617 mg/L at 25 °C Not Available
LogP 3.48 AVDEEF,A (1997)
Predicted Properties
Property Value Source
Water Solubility 0.079 g/L ALOGPS
LogP 3.03 ALOGPS
LogP 2.58 ChemAxon
LogS -3.51 ALOGPS
pKa (strongest acidic) 14.09 ChemAxon
pKa (strongest basic) 9.67 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 41.49 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 76.83 ChemAxon
Polarizability 29.99 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Liver
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified
0.0026 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022707
KNApSAcK ID Not Available
Chemspider ID 4777 Link_out
KEGG Compound ID C07407 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Propranolol Link_out
NuGOwiki Link HMDB01849 Link_out
Metagene Link HMDB01849 Link_out
METLIN ID 2170 Link_out
PubChem Compound 4946 Link_out
PDB ID Not Available
ChEBI ID 8499 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Obach RS: Nonspecific binding to microsomes: impact on scale-up of in vitro intrinsic clearance to hepatic clearance as assessed through examination of warfarin, imipramine, and propranolol. Drug Metab Dispos. 1997 Dec;25(12):1359-69. Pubmed: 9394025 Link_out
  2. Lu C, Li P, Gallegos R, Uttamsingh V, Xia CQ, Miwa GT, Balani SK, Gan LS: Comparison of intrinsic clearance in liver microsomes and hepatocytes from rats and humans: evaluation of free fraction and uptake in hepatocytes. Drug Metab Dispos. 2006 Sep;34(9):1600-5. Epub 2006 Jun 21. Pubmed: 16790553 Link_out

Enzymes
Name: Adenine phosphoribosyltransferase
Reactions: Not Available
Gene Name: APRT
Uniprot ID: P07741 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: AMP deaminase 3
Reactions: Not Available
Gene Name: AMPD3
Uniprot ID: Q01432 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: AMP deaminase 2
Reactions: Not Available
Gene Name: AMPD2
Uniprot ID: Q01433 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenosine kinase
Reactions: Not Available
Gene Name: ADK
Uniprot ID: P55263 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: AMP deaminase 1
Reactions: Not Available
Gene Name: AMPD1
Uniprot ID: P23109 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1 adrenergic receptor
Reactions: Not Available
Gene Name: ADRB1
Uniprot ID: P08588 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-2 adrenergic receptor
Reactions: Not Available
Gene Name: ADRB2
Uniprot ID: P07550 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 1B
Reactions: Not Available
Gene Name: HTR1B
Uniprot ID: P28222 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 1A
Reactions: Not Available
Gene Name: HTR1A
Uniprot ID: P08908 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-3 adrenergic receptor
Reactions: Not Available
Gene Name: ADRB3
Uniprot ID: P13945 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA