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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL27
CHEMBL27
Compound Name PROPRANOLOL
ChEMBL Synonyms Propranolol hydrochloride intensol | Inderal | Tesnol | Sagittol | ICI 45520 | AY-64043 | INNOPRAN | Innopran xl | INDERAL | ICI-45520 | Inderide-80/25 | PROPRANOLOL HYDROCHLORIDE | AY 64043 | Inderide-40/25 | PROPRANOLOL | Inderal la
Max Phase 4 (Approved)
Trade Names INDERAL | Propranolol hydrochloride intensol | Inderal la | Propranolol hydrochloride | Innopran xl | INNOPRAN | Sagittol | Tesnol
Molecular Formula C16H21NO2

Additional synonyms for CHEMBL27 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC(C)NCC(O)COc1cccc2ccccc12
Standard InChI InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3 ...
Download InChI
Standard InChI Key AQHHHDLHHXJYJD-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL27

Molecule Features

CHEMBL27 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Beta-1 adrenergic receptor antagonist Beta-1 adrenergic receptor DailyMed
Beta-2 adrenergic receptor antagonist Beta-2 adrenergic receptor DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
HYPERTENSIOND006973EFO:0000537HYPERTENSION4DailyMed
DailyMed
MELANOMAD008545EFO:0000389CUTANEOUS MELANOMA2ClinicalTrials
DIABETES MELLITUS, TYPE 2D003924EFO:0001360TYPE II DIABETES MELLITUS1ClinicalTrials

Clinical Data

ClinicalTrials.gov PROPRANOLOL
The Cochrane Collaboration PROPRANOLOL

Metabolites for CHEMBL27

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL27. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL3252 Beta-1 adrenergic receptor Rattus norvegicus 1.000
CHEMBL5471 Beta-1 adrenergic receptor Cavia porcellus 1.000
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 1.000
CHEMBL213 Beta-1 adrenergic receptor Homo sapiens 1.000
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 1.000
CHEMBL3373 Beta-2 adrenergic receptor Bos taurus 1.000
CHEMBL246 Beta-3 adrenergic receptor Homo sapiens 1.000
CHEMBL4302 P-glycoprotein 1 Homo sapiens 1.000
CHEMBL1878 Calcium sensing receptor Homo sapiens 0.998
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.857
CHEMBL214 Serotonin 1a (5-HT1a) receptor Homo sapiens 0.804
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 0.421
CHEMBL313 Serotonin transporter Rattus norvegicus 0.225
CHEMBL228 Serotonin transporter Homo sapiens 0.220



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 1.000
CHEMBL3252 Beta-1 adrenergic receptor Rattus norvegicus 1.000
CHEMBL5471 Beta-1 adrenergic receptor Cavia porcellus 1.000
CHEMBL3373 Beta-2 adrenergic receptor Bos taurus 1.000
CHEMBL213 Beta-1 adrenergic receptor Homo sapiens 1.000
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 1.000
CHEMBL246 Beta-3 adrenergic receptor Homo sapiens 1.000
CHEMBL2289 Beta-2 adrenergic receptor Canis lupus familiaris 1.000
CHEMBL4302 P-glycoprotein 1 Homo sapiens 1.000
CHEMBL1878 Calcium sensing receptor Homo sapiens 0.999
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.932
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 0.869
CHEMBL3754 Beta-2 adrenergic receptor Rattus norvegicus 0.858
CHEMBL214 Serotonin 1a (5-HT1a) receptor Homo sapiens 0.800
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.687
CHEMBL3815 Squalene synthetase Rattus norvegicus 0.399
CHEMBL313 Serotonin transporter Rattus norvegicus 0.250
CHEMBL228 Serotonin transporter Homo sapiens 0.223

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
259.3 259.1572 2.54 6 41.48 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 2 0 3 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.84 9.5 2.9 .79 2 19 0.84

Structural Alerts

There are 1 structural alerts for CHEMBL27. To view alerts please click here.

Compound Cross References

ATC C - CARDIOVASCULAR SYSTEM
C07 - BETA BLOCKING AGENTS
C07A - BETA BLOCKING AGENTS
C07AA - Beta blocking agents, non-selective
C07AA05 - propranolol

ChemSpider ChemSpider:AQHHHDLHHXJYJD-UHFFFAOYSA-N
DailyMed propranolol hydrochloride
PubChem SID: 124881056 SID: 26751802 SID: 26755283 SID: 50104497 SID: 90341556
Wikipedia Propranolol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL27



ACToR 525-66-6 13013-17-7
BindingDB 25761
ChEBI 8499
DrugBank DB00571
DrugCentral 2303
eMolecules 735071
EPA CompTox Dashboard DTXSID6023525
Guide to Pharmacology 564
Human Metabolome Database HMDB01849
IBM Patent System E8CE792491FBFDE504024008C3A8AF91
KEGG Ligand C07407
LINCS LSM-4329
Mcule MCULE-7804628650
Metabolights MTBLC8499
Nikkaji J6.653B
PharmGKB PA451145
PubChem 4946
PubChem: Thomson Pharma 14823711
SureChEMBL SCHEMBL3955

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/AQHHHDLHHXJYJD-UHFFFAOYSA-N spacer
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