Esatenolol

Details

• Internal ID: 5b152e6b-a7df-4116-a985-76cd451bd9cb
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylacetamides
• IUPAC Name: 2-[4-[(2S)-2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide
• SMILES (Canonical): CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O
• SMILES (Isomeric): CC(C)NC[C@@H](COC1=CC=C(C=C1)CC(=O)N)O
• InChI: InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)/t12-/m0/s1
• InChI Key: METKIMKYRPQLGS-LBPRGKRZSA-N
• Popularity: 78 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₂N₂O₃
• Molecular Weight: 266.34 g/mol
• Exact Mass: 266.16304257 g/mol
• Topological Polar Surface Area (TPSA): 84.60 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.45
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• (S)-Atenolol
• 93379-54-5
• (S)-(-)-Atenolol
• (-)-Atenolol
• S-Atenolol
• S(-)-Atenolol
• Esatenolol [INN]
• S-(-)-Atenolol
• 2-(p-((2S)-2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide
• Atenolol, (s)-
• S-(-)-4-(2-Hydroxy-3-isopropylaminopropoxy)phenylacetamide
• Atenolol, (-)-
• (S)-4-(2-Hydroxy-3-((1-methylethyl)amino)propoxy)benzeneacetamide
• UNII-DPF757BOSR
• DPF757BOSR
• CHEBI:31556
• 2-[4-[(2S)-2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide
• 2-{4-[(2S)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenyl}acetamide
• Benzeneacetamide, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, (S)-
• (S)-(-)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide
• 2-[4-({(2S)2-hydroxy-3-[(propan-2-yl)amino]propyl}oxy)phenyl]acetamide
• SR-01000597666
• S Atenolol
• Benzeneacetamide, 4-[(2S)-2-hydroxy-3-[(1-methylethyl)amino]propoxy]-
• BENZENEACETAMIDE, 4-((2S)-2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-
• NCGC00093636-03
• atenolol-(-)
• CAS-56715-13-0
• MFCD00074918
• (S)(-)-atenolol
• (S)-()-Atenolol
• Tocris-0387
• Tocris-0393
• Esatenolol (JAN/INN)
• Lopac-A-142
• Lopac-A-143
• ESATENOLOL [JAN]
• (-)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide
• Prestwick0_000536
• Prestwick1_000536
• Prestwick2_000536
• Prestwick3_000953
• Lopac-A-7655
• ESATENOLOL [MART.]
• SCHEMBL4363
• ESATENOLOL [WHO-DD]
• Lopac0_000156
• BSPBio_000946
• MLS002153864
• (S)-(-)-Atenolol, powder
• SPBio_002472
• BPBio1_001042
• CHEMBL343633
• (S)-(-)-Atenolol, 99%
• DTXSID10239405
• METKIMKYRPQLGS-LBPRGKRZSA-N
• HMS2097P08
• HMS2235B16
• HMS3260O14
• HMS3266K19
• HMS3411I05
• HMS3675I05
• HMS3714P08
• Tox21_500156
• GEO-02804
• AKOS015894675
• CCG-204251
• CS-O-07264
• DB13443
• GS-0672
• LP00156
• SDCCGSBI-0050144.P002
• NCGC00015007-01
• NCGC00015007-02
• NCGC00015007-03
• NCGC00015007-04
• NCGC00015007-05
• NCGC00015007-12
• NCGC00016880-01
• NCGC00016880-02
• NCGC00016880-03
• NCGC00016880-04
• NCGC00016880-05
• NCGC00016880-06
• NCGC00016880-07
• NCGC00016880-13
• NCGC00024566-01
• NCGC00024570-01
• NCGC00024570-02
• NCGC00024570-03
• NCGC00024570-04
• NCGC00093636-01
• NCGC00093636-02
• NCGC00260841-01
• LS-28558
• SMR000326748
• CAS-93379-54-5
• A-143
• AB00513856
• EU-0100156
• A13427
• D01471
• EN300-18539569
• SR-01000597666-1
• SR-01000597666-3
• W-200527
• BRD-K44993696-001-03-2
• BRD-K44993696-001-05-7
• Q24255323
• 4-((2S)-2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)BENZENEACETAMIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9936	99.36%
Caco-2	-	0.5218	52.18%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8513	85.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9641	96.41%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7905	79.05%
P-glycoprotein inhibitior	-	0.9348	93.48%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	-	0.6408	64.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4515	45.15%
CYP3A4 inhibition	-	0.9379	93.79%
CYP2C9 inhibition	-	0.9163	91.63%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.9537	95.37%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.7116	71.16%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9897	98.97%
Skin irritation	-	0.7574	75.74%
Skin corrosion	-	0.9379	93.79%
Ames mutagenesis	-	0.9528	95.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.7260	72.60%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.9196	91.96%
Acute Oral Toxicity (c)	III	0.7976	79.76%
Estrogen receptor binding	-	0.6595	65.95%
Androgen receptor binding	-	0.7844	78.44%
Thyroid receptor binding	+	0.5222	52.22%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5230	52.30%
PPAR gamma	-	0.5206	52.06%
Honey bee toxicity	-	0.9426	94.26%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7950	79.50%
Fish aquatic toxicity	-	0.8653	86.53%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2524	P06280	Alpha-galactosidase A	3548.1 nM	Potency	via CMAUP
CHEMBL213	P08588	Beta-1 adrenergic receptor	1.77 nM	IC50	via Super-PRED
CHEMBL210	P07550	Beta-2 adrenergic receptor	260 nM	Kd	via Super-PRED
CHEMBL1293237	P54132	Bloom syndrome protein	2.8 nM; 446683.6 nM; 2.8 nM; 446683.6 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	31622.78 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	39.8 nM; 39.8 nM; 39.8 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	5 nM; 1.6 nM; 1.6 nM	Potency; Potency; Potency	via Super-PRED; via Super-PRED; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	50.1 nM; 50.1 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	70.8 nM; 4 nM; 4 nM	Potency; Potency; Potency	via Super-PRED; via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.51%	98.95%
CHEMBL3437	Q16853	Amine oxidase, copper containing	94.88%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	93.83%	90.17%
CHEMBL2039	P27338	Monoamine oxidase B	92.82%	92.51%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.76%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.35%	94.45%
CHEMBL4208	P20618	Proteasome component C5	91.34%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	89.24%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.15%	95.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.87%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.61%	89.34%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.70%	95.89%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	86.74%	97.29%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.25%	95.56%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	86.05%	100.00%
CHEMBL3902	P09211	Glutathione S-transferase Pi	84.64%	93.81%
CHEMBL2535	P11166	Glucose transporter	84.29%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.92%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.52%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.62%	94.00%

Plants that contains it

• Asarum heterotropoides
• Asarum sieboldii

Cross-Links

• PubChem: 175540
• NPASS: NPC97870
• ChEMBL: CHEMBL343633