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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-16 09:05:30 UTC
Update Date2021-09-14 15:46:28 UTC
HMDB IDHMDB0001849
Secondary Accession Numbers
  • HMDB01849
Metabolite Identification
Common NamePropranolol
DescriptionPropranolol 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
Data?1582752212
Synonyms
ValueSource
1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanolChEBI
1-(Isopropylamino)-3-(1-naphthyloxy)propan-2-olChEBI
beta-PropranololChEBI
PropanalolChEBI
PropanololChEBI
PropranololoChEBI
PropranololumChEBI
b-PropranololGenerator
Β-propranololGenerator
DocitonHMDB, MeSH
EuprovasinHMDB
PropanixHMDB
BetadrenMeSH, HMDB
InderalMeSH, HMDB
ObsidanMeSH, HMDB
ObzidanMeSH, HMDB
Propranolol hydrochlorideMeSH, HMDB
AnaprilineMeSH, HMDB
RexigenMeSH, HMDB
AvlocardylMeSH, HMDB
DexpropranololMeSH, HMDB
Hydrochloride, propranololMeSH, HMDB
AnaprilinMeSH, HMDB
Chemical FormulaC16H21NO2
Average Molecular Weight259.3434
Monoisotopic Molecular Weight259.157228921
IUPAC Name1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-ol
Traditional Namepropranolol
CAS Registry Number525-66-6
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 KeyAQHHHDLHHXJYJD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Alkyl aryl ether
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point96 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.062 mg/L at 25 °CNot Available
LogP3.48AVDEEF,A (1997)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM162.730932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.079 g/LALOGPS
logP10(3.03) g/LALOGPS
logP10(2.58) g/LChemAxon
logS10(-3.5) g/LALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity76.83 m³·mol⁻¹ChemAxon
Polarizability29.98 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.33731661259
DarkChem[M-H]-157.22931661259
AllCCS[M+H]+163.02832859911
AllCCS[M-H]-166.57632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PropranololCC(C)NCC(O)COC1=CC=CC2=CC=CC=C122924.4Standard polar33892256
PropranololCC(C)NCC(O)COC1=CC=CC2=CC=CC=C122128.5Standard non polar33892256
PropranololCC(C)NCC(O)COC1=CC=CC2=CC=CC=C122138.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Propranolol,1TMS,isomer #1CC(C)NCC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C2145.2Semi standard non polar33892256
Propranolol,1TMS,isomer #2CC(C)N(CC(O)COC1=CC=CC2=CC=CC=C12)[Si](C)(C)C2327.1Semi standard non polar33892256
Propranolol,2TMS,isomer #1CC(C)N(CC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C)[Si](C)(C)C2375.7Semi standard non polar33892256
Propranolol,2TMS,isomer #1CC(C)N(CC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C)[Si](C)(C)C2397.2Standard non polar33892256
Propranolol,2TMS,isomer #1CC(C)N(CC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C)[Si](C)(C)C2745.0Standard polar33892256
Propranolol,1TBDMS,isomer #1CC(C)NCC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C(C)(C)C2395.0Semi standard non polar33892256
Propranolol,1TBDMS,isomer #2CC(C)N(CC(O)COC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C2609.3Semi standard non polar33892256
Propranolol,2TBDMS,isomer #1CC(C)N(CC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2849.7Semi standard non polar33892256
Propranolol,2TBDMS,isomer #1CC(C)N(CC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2809.8Standard non polar33892256
Propranolol,2TBDMS,isomer #1CC(C)N(CC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2922.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Propranolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r6-9610000000-d6d87b61c182e2ab976e2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propranolol GC-MS (1 TMS) - 70eV, Positivesplash10-006x-5900000000-e799ecbefa830180bc012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propranolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propranolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propranolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propranolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-03di-0090000000-f8c39664b694f57848652012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-05fr-9000000000-84923a2dc3053801527a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0fk9-2932000000-fa245a17a643ef33a0b22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-03di-0090000000-ee9d9c871e322202a9482012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-03di-0290000000-9f3f72a6b6b7926591372012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0avi-5900000000-95293e6a5f843d0cc2822012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0ab9-9700000000-6b5b9e9743cb3f7bca582012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-0adi-9700000000-f5825268222d45a4ce952012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0159-1900000000-9872255282c6a95633aa2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00di-9500000000-122203085c028de6cbe42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0aor-0900000000-39e75b6ae19b4763a0bf2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-004i-0900000000-b75e7bf7aa20ce8541572012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00di-9200000000-2f102916e2fe0f6c1f4b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-QTOF , positive-QTOFsplash10-0c00-9650000000-c4a4f189be72c438d0802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-ITFT , positive-QTOFsplash10-0159-0910000000-d7db5bab374a7cf02fd32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-ITFT , positive-QTOFsplash10-03di-0090000000-057a63162f5e674c4ce62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-ITFT , positive-QTOFsplash10-03di-0190000000-87c354c205b94f5f06e12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-ITFT , positive-QTOFsplash10-0cl0-4930000000-1eecec66280a12a94b9d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propranolol LC-ESI-ITFT , positive-QTOFsplash10-0ab9-4900000000-ddd58df17ce1f65a75592017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propranolol 10V, Positive-QTOFsplash10-03di-1290000000-2d6ddc1435f3b48e71892017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propranolol 20V, Positive-QTOFsplash10-0g4i-9580000000-2e146983ce2a203029232017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propranolol 40V, Positive-QTOFsplash10-05fv-9400000000-1ee35eae3a4de309c80f2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propranolol 10V, Negative-QTOFsplash10-0a4l-1690000000-4f37e99073c51d06c4192017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propranolol 20V, Negative-QTOFsplash10-0006-0900000000-aacf3eb3805a8fb724542017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propranolol 40V, Negative-QTOFsplash10-0006-1900000000-b607646c7ffdb9665d122017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0026 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00571
Phenol Explorer Compound IDNot Available
FooDB IDFDB022707
KNApSAcK IDNot Available
Chemspider ID4777
KEGG Compound IDC07407
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropranolol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID8499
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot 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 ]
  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 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Enzymes

General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535
General function:
Involved in deaminase activity
Specific function:
AMP deaminase plays a critical role in energy metabolism.
Gene Name:
AMPD3
Uniprot ID:
Q01432
Molecular weight:
89727.485
General function:
Involved in deaminase activity
Specific function:
AMP deaminase plays a critical role in energy metabolism.
Gene Name:
AMPD2
Uniprot ID:
Q01433
Molecular weight:
100686.95
General function:
Involved in adenosine kinase activity
Specific function:
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intracellular adenine nucleotides.
Gene Name:
ADK
Uniprot ID:
P55263
Molecular weight:
38702.93
General function:
Involved in deaminase activity
Specific function:
AMP deaminase plays a critical role in energy metabolism.
Gene Name:
AMPD1
Uniprot ID:
P23109
Molecular weight:
90218.455
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5

Only showing the first 10 proteins. There are 12 proteins in total.