Propranolol

Details

• Internal ID: 9337c2c4-cefb-40b4-a8c9-3acba5e06017
• Taxonomy: Benzenoids > Naphthalenes
• IUPAC Name: 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol
• SMILES (Canonical): CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O
• SMILES (Isomeric): CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O
• InChI: 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
• Popularity: 64,446 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.34 g/mol
• Exact Mass: 259.157228913 g/mol
• Topological Polar Surface Area (TPSA): 41.50 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• Propanolol
• 525-66-6
• beta-Propranolol
• Betalong
• Euprovasin
• Proprasylyt
• Reducor
• Propanalol
• Propanix
• Avlocardyl
• Dociton
• propranololo
• Betadren
• Corpendol
• Sawatal
• dl-propranolol
• Sumial
• Anapriline
• Racemic propranolol
• Propranololum
• D,L-Propranolol
• (+-)-Propranolol
• racemic-Propranolol
• .beta.-Propranolol
• Propranololo [DCIT]
• hemangiol
• CCRIS 3082
• 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol
• Propranolol [INN:BAN]
• 1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanol
• 1-(isopropylamino)-3-(1-naphthyloxy)propan-2-ol
• Propanolol [INN-Spanish]
• UNII-9Y8NXQ24VQ
• Propranololum [INN-Latin]
• EINECS 208-378-0
• EINECS 235-867-6
• 9Y8NXQ24VQ
• 1-Isopropylamino-3-(1-naphthyloxy)-2-propanol
• Bedranol
• CHEBI:8499
• 2-Propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)-
• (+/-)-propranolol
• 2-Propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-
• CHEMBL27
• Propranalol
• Obzidan
• AY-64043-
• AY-20694
• DTXSID6023525
• 2-Propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-, (+-)-
• 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-
• Inderex
• Inderol
• Pranolol
• Propranolol (INN)
• (1)-1-(Isopropylamino)-3-(naphthyloxy)propan-2-ol
• 1-Isopropylamino-3-(naphthalen-1-yloxy)-propan-2-ol
• PROPRANOLOL [INN]
• 2-Propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)-, (+-)-
• Inderal hydrochloride
• 13013-17-7
• 3-(naphthalen-1-yloxy)-1-(propan-2-ylamino)propan-2-ol
• [2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine
• 1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-ol
• Propranolol (TN)
• AY 20694
• 1-(naphthalen-1-yloxy)-3-(propan-2-ylamino)propan-2-ol
• INDERIDE-40/25
• INDERIDE-80/25
• (S)-(-)-PROPRANOLOL
• 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol
• b-Propranolol
• Dociton (Salt/Mix)
• Inderal (Salt/Mix)
• Obsidan (Salt/Mix)
• Propanolol,(+/-)
• PROPRANOLOL, d
• Avlocardyl (Salt/Mix)
• beta-Propranolol;Dociton
• 1-(Isopropylamino)-3-(1-naphthoxy)-propan-2-ol
• PROPANOLOL(-)
• PROPRANOLOL [MI]
• Prestwick0_000952
• Prestwick1_000952
• Prestwick2_000952
• Prestwick3_000952
• PROPRANOLOL,(+)
• PROPRANOLOL,(-)
• Spectrum2_001301
• Spectrum2_001699
• Spectrum3_000883
• Spectrum3_001071
• Spectrum4_000974
• Spectrum4_001222
• Spectrum5_000751
• (.+/-.)-Propranolol
• 1-(1-Naphthyloxy)-2-hydroxy-3-(isopropylamino)propane
• PROPRANOLOL [VANDF]
• SCHEMBL3955
• 3-[(methylethyl)amino]-1-naphthyloxypropan-2-ol
• Lopac0_000896
• Oprea1_304193
• BSPBio_000944
• BSPBio_002682
• CBDivE_006180
• GTPL564
• KBioGR_001347
• KBioGR_001684
• KBioGR_002515
• KBioSS_002523
• PROPRANOLOL [WHO-DD]
• 1-[(1-methylethyl)amino]-3-(naphthalen-1-yloxy)propan-2-ol
• DivK1c_000023
• SPBio_001361
• SPBio_001658
• SPBio_003093
• (+)-Propranolol hydrochloride; (R)-(+)-Propranolol hydrochloride
• 1-(Isopropylamino)-3-(naphthalen-1-yloxy)propan-2-ol
• BPBio1_001040
• DTXCID903525
• ICI 45520 (Salt/Mix)
• NSC 91523 (Salt/Mix)
• SCHEMBL12264958
• BDBM25761
• HY-B0573B
• KBio1_000023
• KBio2_002515
• KBio2_005083
• KBio2_007651
• KBio3_001766
• KBio3_001902
• KBio3_002993
• C07AA05
• cMAP_000071
• NINDS_000023
• (A+/-)-Propranolol hydrochloride
• Bio1_000367
• Bio1_000856
• Bio1_001345
• HMS2090L21
• HMS3428G03
• BCP26001
• BCP31343
• BBL023437
• PDSP1_000767
• PDSP1_001607
• PDSP1_001608
• PDSP2_000755
• PDSP2_001591
• PDSP2_001592
• STK735510
• AKOS000588816
• AKOS016050338
• CCG-103643
• DB00571
• FE-0204
• SDCCGSBI-0050871.P004
• IDI1_000023
• NCGC00015798-04
• NCGC00015798-05
• NCGC00015798-06
• NCGC00015798-07
• NCGC00015798-08
• NCGC00015798-09
• NCGC00015798-15
• NCGC00015798-19
• NCGC00024690-02
• NCGC00024690-03
• SBI-0050871.P003
• LS-122410
• LS-184129
• AB00053537
• CS-0069968
• FT-0650563
• FT-0674088
• EN300-40731
• C07407
• D08443
• AB00053537-10
• AB00053537_11
• AB00053537_12
• L000679
• Q423364
• 1(-alpha-naphthoxy)-3-(iso-propylamino)-2-propanol
• 1-(alpha-naphthoxy)-3-(iso-propylamino)-2-propanol
• 1-(alpha-naphthoxy)-3-(isopropylamino)-2-propanol
• 1-isopropylamino-3-(naphthalen-1-yloxy)propan-2-ol
• W-109550
• (+-)-1-(isopropylamino)-3-(naphthyloxy)propan-2-ol
• 1-(isopropylamino)-3-naphthalen-1-yloxy-propan-2-ol
• BRD-A10070317-003-06-9
• BRD-A10070317-003-17-6
• 1-((1-Methylethyl)amino)-3-(1-naphthyloxy)-2-propanol
• F0001-3681
• 2-Propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-, (.+.)-
• 2-Propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)-, (+)-
• 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, (.+-.)-
• 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, (.+.)-
• 1H-Pyrrole-2-carboxylic acid, 4-acetyl-5-methyl-3-(trifluoromethyl)-, ethyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	+	0.8631	86.31%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5573	55.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9624	96.24%
OATP1B3 inhibitior	+	0.9452	94.52%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8666	86.66%
P-glycoprotein inhibitior	-	0.9338	93.38%
P-glycoprotein substrate	-	0.7777	77.77%
CYP3A4 substrate	-	0.5939	59.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.7090	70.90%
CYP3A4 inhibition	-	0.9240	92.40%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.9301	93.01%
CYP inhibitory promiscuity	-	0.8487	84.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.7002	70.02%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.6720	67.20%
Skin corrosion	-	0.9141	91.41%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7468	74.68%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.7976	79.76%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	III	0.7956	79.56%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.8123	81.23%
Thyroid receptor binding	+	0.5215	52.15%
Glucocorticoid receptor binding	-	0.8599	85.99%
Aromatase binding	-	0.7711	77.11%
PPAR gamma	+	0.5812	58.12%
Honey bee toxicity	-	0.9107	91.07%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.4897	48.97%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	15.8 nM	Potency	via Super-PRED
CHEMBL213	P08588	Beta-1 adrenergic receptor	18 nM; 1.4 nM; 1.4 nM; 2.543 nM	IC50; Ki; Ki; IC50	PMID: 1976812; via Super-PRED; via Super-PRED; via CMAUP
CHEMBL210	P07550	Beta-2 adrenergic receptor	0.54 nM; 50.12 nM; 0.1 nM; 1.116 nM	Ki; IC50; Kd; IC50	via Super-PRED; PMID: 26565745; via Super-PRED; via CMAUP
CHEMBL246	P13945	Beta-3 adrenergic receptor	162.18 nM; 132 nM	Kd; IC50	via Super-PRED; via CMAUP
CHEMBL5287	Q14973	Bile acid transporter	5500 nM	IC50	PMID: 10565843
CHEMBL3356	P05177	Cytochrome P450 1A2	4000 nM	IC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	2000 nM; 1900 nM	IC50; IC50	via CMAUP; PMID: 15993593
CHEMBL240	Q12809	HERG	2828 nM	IC50	PMID: 21300721
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	631 nM	Potency	via Super-PRED
CHEMBL4302	P08183	P-glycoprotein 1	573000 nM	IC50	PMID: 12477351
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	3981.07 nM	IC50	PMID: 26565745
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	1466 nM	IC50	via CMAUP
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	342 nM	IC50	via CMAUP
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	2294 nM	IC50	via CMAUP
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	3065 nM	IC50	via CMAUP
CHEMBL228	P31645	Serotonin transporter	380 nM	IC50	via CMAUP
CHEMBL287	Q99720	Sigma opioid receptor	2870 nM	IC50	via CMAUP
CHEMBL1980	Q14524	Sodium channel protein type V alpha subunit	2100 nM	IC50	PMID: 21300721
CHEMBL1293256	P40225	Thrombopoietin	316.2 nM	Potency	via Super-PRED
CHEMBL1940	Q13936	Voltage-gated L-type calcium channel alpha-1C subunit	21000 nM	IC50	PMID: 22761000

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.14%	89.76%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.09%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.00%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.78%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.88%	94.73%
CHEMBL2535	P11166	Glucose transporter	90.18%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.45%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.51%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.93%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.06%	86.33%
CHEMBL2885	P07451	Carbonic anhydrase III	84.32%	87.45%
CHEMBL3085	P43003	Excitatory amino acid transporter 1	83.58%	94.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.94%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.77%	92.62%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.53%	96.67%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.00%	82.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.90%	89.62%

Plants that contains it

• Myristica fragrans

Cross-Links

• PubChem: 4946
• NPASS: NPC318591
• ChEMBL: CHEMBL27
• LOTUS: LTS0020870
• wikiData: Q423364