Alprenolol

Details

• Internal ID: 34c6b198-382c-4c8a-915d-f70a8dad0bfc
• Taxonomy: Benzenoids > Phenol ethers
• IUPAC Name: 1-(propan-2-ylamino)-3-(2-prop-2-enylphenoxy)propan-2-ol
• SMILES (Canonical): CC(C)NCC(COC1=CC=CC=C1CC=C)O
• SMILES (Isomeric): CC(C)NCC(COC1=CC=CC=C1CC=C)O
• InChI: InChI=1S/C15H23NO2/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3
• InChI Key: PAZJSJFMUHDSTF-UHFFFAOYSA-N
• Popularity: 2,771 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₃NO₂
• Molecular Weight: 249.35 g/mol
• Exact Mass: 249.172878976 g/mol
• Topological Polar Surface Area (TPSA): 41.50 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.15
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

• 13655-52-2
• Alpheprol
• Alfeprol
• Alprenololum
• Alfeprol [Russian]
• Alprenololum [INN-Latin]
• 1-(o-Allylphenoxy)-3-(isopropylamino)-2-propanol
• Alprenolol [INN:BAN]
• (RS)-Alprenolol;dl-Alprenolol
• 1-(2-Allylphenoxy)-3-isopropylamino-2-propanol
• (RS)-Alprenolol
• Alprenolol (INN)
• 2-Propanol, 1-(o-allylphenoxy)-3-(isopropylamino)-
• 2-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propenyl)phenoxy]-
• 1-(propan-2-ylamino)-3-(2-prop-2-enylphenoxy)propan-2-ol
• EINECS 237-140-9
• S-(-)-ALPRENOLOL
• (-)-1-(o-Allylphenoxy)-3-(isopropylamino)-2-propanol
• UNII-877K5MQ27W
• CHEMBL266195
• 122259-67-0
• DTXSID0045127
• CHEBI:51211
• 2-Propanol, 1-((1-methylethyl)amino)-3-(2-(2-propenyl)phenoxy)-
• 877K5MQ27W
• H-56-28
• NSC-759561
• (+/-)-Alprenolol
• NCGC00015099-05
• ALPRENOLOL [INN]
• Regletin (TN)
• 1-(o-Allylphenoxy)-3-isopropylamino)-2-propanol
• DTXCID8025127
• 1-[2-(propen-2-ylphenoxy)]-3-(isopropylamino)propan-2-ol
• {2-hydroxy-3-[2-(prop-2-en-1-yl)phenoxy]propyl}(propan-2-yl)amine
• CAS-13655-52-2
• Aprenololo
• Atenenol
• Apllobal (TN)
• Gubernal (TN)
• Duriles (TN)
• Aptine (TN)
• Aptol (TN)
• Yobir (TN)
• Spectrum_000168
• ALPRENOLOL [MI]
• Prestwick0_000250
• Prestwick1_000250
• Prestwick2_000250
• Prestwick3_000250
• Spectrum2_001814
• Spectrum3_001066
• Spectrum4_001216
• Spectrum5_001414
• ALPRENOLOL,(+)
• ALPRENOLOL,(-)
• D01VAB
• ALPRENOLOL [MART.]
• ALPRENOLOL [WHO-DD]
• Lopac0_000152
• Oprea1_368995
• SCHEMBL34636
• BSPBio_000040
• BSPBio_002652
• GTPL563
• KBioGR_001652
• KBioSS_000648
• 1-(isopropylamino)-3-(2-allylphenoxy)-2-propanol
• DivK1c_000015
• SPBio_001827
• SPBio_002259
• BPBio1_000044
• (RS)-Alprenolol; dl-Alprenolol
• BDBM25764
• KBio1_000015
• KBio2_000648
• KBio2_003216
• KBio2_005784
• KBio3_001872
• NINDS_000015
• HMS2089G06
• BCP29423
• HY-B1517
• Tox21_110084
• MFCD00242735
• AKOS016376219
• Tox21_110084_1
• CCG-204247
• CS-5734
• DB00866
• NSC 759561
• SDCCGSBI-0050140.P004
• IDI1_000015
• NCGC00015099-03
• NCGC00015099-04
• NCGC00015099-06
• NCGC00015099-08
• NCGC00015099-09
• NCGC00015099-11
• NCGC00015099-12
• NCGC00015099-16
• NCGC00089741-02
• NCGC00089741-03
• NCGC00089741-04
• MS-23533
• SBI-0050140.P003
• LS-121647
• AB00053431
• D07156
• F85411
• AB00053431-13
• AB00053431_14
• A903070
• L000961
• Q201370
• 1-(2-Allylphenoxy)-3-(isopropylamino)-2-propanol #
• BRD-A00993607-003-05-5
• BRD-A00993607-003-15-4
• (RS)-1-(2-allylphenoxy)-3-(isopropylamino)propan-2-ol
• 1-[2-(prop-2-en-1-yl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol
• 1-[(1-Methylethyl)amino]-3-[2-(2-propen-1-yl)phenoxy]-2-propanol
• 2-PROPANOL, 1-((1-METHYLETHYL)AMINO)-3-)2-(2-PROPENYL)PHENOXY)-
• 2-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propen-1-yl)phenoxy]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.9714	97.14%
Subcellular localzation	Mitochondria	0.8836	88.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.8555	85.55%
P-glycoprotein inhibitior	-	0.9381	93.81%
P-glycoprotein substrate	-	0.9317	93.17%
CYP3A4 substrate	-	0.7355	73.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6762	67.62%
CYP3A4 inhibition	-	0.8839	88.39%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.9137	91.37%
CYP inhibitory promiscuity	-	0.8933	89.33%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.7445	74.45%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9036	90.36%
Skin irritation	-	0.6896	68.96%
Skin corrosion	-	0.8420	84.20%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6857	68.57%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.6363	63.63%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.7603	76.03%
Acute Oral Toxicity (c)	III	0.7047	70.47%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.9178	91.78%
Thyroid receptor binding	+	0.5785	57.85%
Glucocorticoid receptor binding	-	0.7746	77.46%
Aromatase binding	-	0.7753	77.53%
PPAR gamma	-	0.5767	57.67%
Honey bee toxicity	-	0.7947	79.47%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.8010	80.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL213	P08588	Beta-1 adrenergic receptor	4.266 nM; 4.88 nM	Kd; IC50	via Super-PRED; PMID: 6126588
CHEMBL210	P07550	Beta-2 adrenergic receptor	1 nM; 0.2951 nM; 0.7244 nM; 2.344 nM	Ki; Kd; IC50; IC50	PMID: 24454993; via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL246	P13945	Beta-3 adrenergic receptor	75.86 nM	Kd	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	15848.9 nM	Potency	via CMAUP
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	21.6 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	98.94%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.69%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.22%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.25%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.20%	94.73%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.78%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.34%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.88%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.71%	86.33%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.71%	82.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.12%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.04%	99.17%
CHEMBL4208	P20618	Proteasome component C5	82.45%	90.00%

Plants that contains it

• Piper nigrum

Cross-Links

• PubChem: 2119
• NPASS: NPC141739
• ChEMBL: CHEMBL266195