Penbutolol (CED0012048)

Record Information

Version

1.0

Creation Date

2016-05-25 18:27:09 UTC

Update Date

2026-08-20 01:23:09 UTC

Accession Number

CHEM022295

Identification

Common Name

Penbutolol

Class

Small Molecule

Description

Penbutolol is an organic compound with the chemical formula C18H29NO2 and an average molecular weight of 291.43 g/mol. Penbutolol belongs to the phenol ethers, a class of benzenoids within the organic compounds. This compound is found in or released from two recorded sources: electrically stimulated smoking devices (Electrical & Electronic Equipment) and beta blocking agents (Healthcare, pharmaceuticals & veterinary products). The recorded exposure route for this substance is oral. Penbutolol interacts with four recorded protein targets. It acts as an antagonist/antagonist or a partial agonist of the Beta-1 adrenergic receptor (ADRB1), the Beta-2 adrenergic receptor (ADRB2), the 5-hydroxytryptamine receptor 1A (HTR1A), and the 5-hydroxytryptamine receptor 1B (HTR1B).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Levatol	HMDB
Hoe-893D	HMDB
Penbutolol sulfate	HMDB
Betapressin	HMDB
Hoe893d	HMDB
Sulfate, penbutolol	HMDB
Hoe 893D	HMDB
Penbutolol sulfate (2:1)	HMDB

Chemical Formula

C₁₈H₂₉NO₂

Average Molecular Mass

291.428 g/mol

Monoisotopic Mass

291.220 g/mol

CAS Registry Number

36507-48-9

IUPAC Name

(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol

Traditional Name

(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol

SMILES

CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1

InChI Identifier

InChI=1S/C18H29NO2/c1-18(2,3)19-12-15(20)13-21-17-11-7-6-10-16(17)14-8-4-5-9-14/h6-7,10-11,14-15,19-20H,4-5,8-9,12-13H2,1-3H3/t15-/m0/s1

InChI Key

KQXKVJAGOJTNJS-HNNXBMFYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ethanolamines (CHEBI:7954 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.84	ALOGPS
logP	3.55	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.6 m³·mol⁻¹	ChemAxon
Polarizability	34.58 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-07jr-9670000000-a79fb91d287e7cfdc751	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00di-9723000000-f4da418202c281b26d1c	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-2290000000-ace7f5ff44fdb9b5b791	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-9570000000-00b3838f0255ecd5c823	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dr-9200000000-cebecfe8b8e40ed053bd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ox-1790000000-ca08d570c87a1a04dad1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-1900000000-d9272a3fe0f9ad9dbffe	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03xu-8900000000-2e9694efe38bd6f12d89	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-2090000000-64af498c50d53a85c9da	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00ko-3390000000-f73c88fee4aee3b02b3f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9200000000-5d04f85a5d512559ca56	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ox-0790000000-19293d327932c94fb42c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0910000000-b2fd879060ccb5ebf563	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02tc-8900000000-992ab80beaa1f5031430	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
995.0	Log mg/kg	[560:1800]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
293	Beta blocking agents	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available

Pathways

4 pathways

Penbutolol Action Pathway

Penbutolol Action Pathway (New)

Penbutolol Drug Metabolism

Penbutolol Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Arylamine N-acetyltransferase	O86309	Mycolicibacterium smegmatis	Predicted (SEA)	0.155698
Click to view 3D structure	Beta-1 adrenergic receptor	P08588	Humans	Predicted (SEA)	7.08428
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Predicted (SEA)	10.0426
Click to view 3D structure	Beta-2 adrenergic receptor	Q8K4Z4	Cavia porcellus	Predicted (SEA)	4.67095
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	47.0209
Click to view 3D structure	Beta-3 adrenergic receptor	P13945	Humans	Predicted (SEA)	8.09632
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	51.1469
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	70.3757
Click to view 3D structure	Beta-1 adrenergic receptor	B0FL73	Cavia porcellus	Predicted (SEA)	3.50322
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	80.8075
Click to view 3D structure	Beta-1 adrenergic receptor	P18090	Rattus norvegicus	Predicted (SEA)	3.34752
Click to view 3D structure	Extracellular calcium-sensing receptor	P41180	Humans	Predicted (SEA)	1.94623
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	223.272
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	50.2906
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	46.3203
Click to view 3D structure	Beta-2 adrenergic receptor	Q28044	Bos taurus	Predicted (SEA)	2.56902
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	151.339
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28564	Rattus norvegicus	Predicted (SEA)	31.1397
Click to view 3D structure	Extracellular calcium-sensing receptor	P35384	Bos taurus	Predicted (SEA)	1.47914
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	85.712
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	179.053
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	136.08
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	95.0539
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	104.629
Click to view 3D structure	Beta-2 adrenergic receptor	P54833	Canis lupus familiaris	Predicted (SEA)	3.65891