Dexpropranolol

Details

• Internal ID: 2ea66089-4ae9-4071-bb35-9af87553f050
• Taxonomy: Benzenoids > Naphthalenes
• IUPAC Name: (2R)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol
• 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/t14-/m1/s1
• InChI Key: AQHHHDLHHXJYJD-CQSZACIVSA-N
• Popularity: 33,590 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

• 5051-22-9
• (+)-Propranolol
• D-Propranolol
• 2R-Propranolol
• (R)-(+)-propranolol
• R-(+)-Propranolol
• Dextropropranolol
• Dexpropranololum
• R (+)-Propanolol
• Despropranolo
• Propranolol, (r)-
• (+)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol
• (2R)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol
• PG6KY07UD7
• DTXSID3045304
• CHEBI:8736
• DTXCID1025304
• (2R)-3-(naphthalen-1-yloxy)-1-(propan-2-ylamino)propan-2-ol
• RefChem:585865
• 225-749-2
• (R)-Propranolol
• R(+)-propranolol
• NCGC00016429-05
• 2-Propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-, (+)-
• 2-Propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)-, (R)-
• 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, (2R)-
• (2R)-1-(Isopropylamino)-3-(1-naphthyloxy)propan-2-ol
• Despropranolo [DCIT]
• MLS001333595
• (2R)-1-[(1-Methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol
• 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, (R)-
• Dexpropranolol [INN:BAN]
• (R)-Propranolol (hydrochloride)
• Dexpropranololum [INN-Latin]
• CAS-5051-22-9
• SMR000875288
• EINECS 225-749-2
• UNII-PG6KY07UD7
• propranolol-(R)
• RNP
• MFCD00066275
• d-(+)-Propranolol
• (2R)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol;hydrochloride
• Tocris-0624
• Tocris-0835
• (+)-(r)-propranolol
• Prestwick0_001075
• Prestwick1_001075
• Prestwick2_001075
• Lopac-P-0884
• Lopac-P-8688
• CAS-318-98-9
• DEXPROPRANOLOL [INN]
• SCHEMBL25255
• cid_66366
• BIDD:GT0130
• SPBio_002995
• (+)-Propranolol hydrochloride; (R)-(+)-Propranolol hydrochloride
• CHEMBL275742
• GTPL7596
• SCHEMBL29577201
• BDBM60973
• (2R)-1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-ol
• Tox21_110435
• PDSP1_000775
• PDSP1_001089
• PDSP2_000763
• PDSP2_001073
• AKOS025212355
• Tox21_110435_1
• CAS-839971
• DB03322
• NCGC00015798-01
• NCGC00015798-02
• NCGC00015798-03
• NCGC00015798-11
• NCGC00016429-01
• NCGC00016429-02
• NCGC00016429-03
• NCGC00016429-04
• NCGC00016429-06
• NCGC00024690-01
• NCGC00024814-01
• NCGC00024814-02
• AS-87283
• CAS-13071-11-9
• AB00514691
• NS00081002
• G77788
• BRD-K92830582-003-04-8
• BRD-K92830582-003-10-5
• Q27088458
• (+)-1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol
• (R)-1-(isopropylamino)-3-(naphthalen-1-yloxy)propan-2-ol
• 1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol, (R)-
• (2R)-1-(isopropylamino)-3-(1-naphthoxy)propan-2-ol;hydrochloride
• (2R)-1-[(Naphthalen-1-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol
• (2R)-1-(1-naphthalenyloxy)-3-(propan-2-ylamino)-2-propanol;hydrochloride

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	1.4 nM; 1.4 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL210	P07550	Beta-2 adrenergic receptor	0.54 nM; 0.1 nM	Ki; Kd	via Super-PRED; via Super-PRED
CHEMBL246	P13945	Beta-3 adrenergic receptor	162.18 nM	Kd	via Super-PRED
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	631 nM	Potency	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	316.2 nM	Potency	via Super-PRED

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

There are no matching plants.

Cross-Links

• PubChem: 21138
• LOTUS: LTS0015919
• wikiData: Q27088458