Showing Compound Propranolol (FDB022707)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:16 UTC

Update date

2015-10-09 22:30:55 UTC

Primary ID

FDB022707

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Propranolol

Description

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. [HMDB]

CAS Number

525-66-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanol	ChEBI
1-(Isopropylamino)-3-(1-naphthyloxy)propan-2-ol	ChEBI
beta-Propranolol	ChEBI
Propanalol	ChEBI
Propanolol	ChEBI
Propranololo	ChEBI
Propranololum	ChEBI
b-Propranolol	Generator
Β-propranolol	Generator
Dociton	HMDB, MeSH
Euprovasin	HMDB
Propanix	HMDB
Betadren	MeSH, HMDB
Inderal	MeSH, HMDB
Obsidan	MeSH, HMDB
Obzidan	MeSH, HMDB
Propranolol hydrochloride	MeSH, HMDB
Anapriline	MeSH, HMDB
Rexigen	MeSH, HMDB
Avlocardyl	MeSH, HMDB
Dexpropranolol	MeSH, HMDB
Hydrochloride, propranolol	MeSH, HMDB
Anaprilin	MeSH, HMDB
β-propranolol	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.079 g/L	ALOGPS
logP	3.03	ALOGPS
logP	2.58	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.67	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	6	ChemAxon
Refractivity	76.83 m³·mol⁻¹	ChemAxon
Polarizability	29.98 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

Chemical Formula

C16H21NO2

IUPAC name

1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-ol

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

Isomeric SMILES

CC(C)NCC(O)COC1=CC=CC2=CC=CC=C12

Average Molecular Weight

259.3434

Monoisotopic Molecular Weight

259.157228921

Classification

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

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 Framework

Aromatic homopolycyclic compounds

External Descriptors

secondary amine (CHEBI:8499 )
propanolamine (CHEBI:8499 )
naphthalenes (CHEBI:8499 )

Ontology

Disposition

Biological location:

Organ and components:

Liver

Subcellular:

Biofluid and excreta:

Urine

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Propranolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00r6-9610000000-d6d87b61c182e2ab976e	Spectrum
Predicted GC-MS	Propranolol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-5900000000-e799ecbefa830180bc01	Spectrum
Predicted GC-MS	Propranolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Propranolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Propranolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Propranolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0090000000-f8c39664b694f5784865	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-05fr-9000000000-84923a2dc3053801527a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0fk9-2932000000-fa245a17a643ef33a0b2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03di-0090000000-ee9d9c871e322202a948	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-03di-0290000000-9f3f72a6b6b792659137	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0avi-5900000000-95293e6a5f843d0cc282	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0ab9-9700000000-6b5b9e9743cb3f7bca58	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0adi-9700000000-f5825268222d45a4ce95	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0159-1900000000-9872255282c6a95633aa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-9500000000-122203085c028de6cbe4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0aor-0900000000-39e75b6ae19b4763a0bf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-004i-0900000000-b75e7bf7aa20ce854157	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-9200000000-2f102916e2fe0f6c1f4b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0c00-9650000000-c4a4f189be72c438d080	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0159-0910000000-d7db5bab374a7cf02fd3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0090000000-057a63162f5e674c4ce6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0190000000-87c354c205b94f5f06e1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0cl0-4930000000-1eecec66280a12a94b9d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0ab9-4900000000-ddd58df17ce1f65a7559	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1290000000-2d6ddc1435f3b48e7189	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0g4i-9580000000-2e146983ce2a20302923	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fv-9400000000-1ee35eae3a4de309c80f	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4l-1690000000-4f37e99073c51d06c419	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-aacf3eb3805a8fb72454	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1900000000-b607646c7ffdb9665d12	2017-07-26	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

8499

Phenol-Explorer ID

Not Available

DrugBank ID

DB00571

HMDB ID

HMDB01849

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Propranolol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Beta-1 adrenergic receptor	ADRB1	P08588
Beta-2 adrenergic receptor	ADRB2	P07550
AMP deaminase 3	AMPD3	Q01432
AMP deaminase 2	AMPD2	Q01433
AMP deaminase 1	AMPD1	P23109
Adenine phosphoribosyltransferase	APRT	P07741
5-hydroxytryptamine receptor 1B	HTR1B	P28222
5-hydroxytryptamine receptor 1A	HTR1A	P08908