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4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol

AlkaPlorer ID: AK323743

Synonym: None

IUPAC Name: 4-[(Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol

Structure

SMILES: CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1

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InChI: InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-

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InChIKey: TXUZVZSFRXZGTL-QPLCGJKRSA-N

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Reference

PubChem CID: 449459

CAS: 65213-48-1

NPASS: NPC484424

Source

Species Genus Family Order Class Phylum Kingdom Domain
Penicillium aurantiacobrunneum Penicillium Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota

Properties Information

Molecule Weight: 387.523

TPSA？: 32.7

MolLogP？: 5.701700000000005

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 39810.7 nM None
Chlorocebus sabaeus Vero CC50 19400.0 nM None
Chlorocebus sabaeus Vero IC50 15100.0 nM 10.1016/j.bmc.2021.116185
Equus caballus Ferritin light chain Potency 31622.8 nM None
Homo sapiens Androgen Receptor Potency 39810.7 nM None
Homo sapiens Androgen Receptor Potency 44668.4 nM None
Homo sapiens Ataxin-2 Potency 39810.7 nM None
Homo sapiens Beta-glucocerebrosidase Potency 19952.6 nM None
Homo sapiens Bile acid receptor FXR Potency 50118.7 nM None
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 44668.4 nM None
Homo sapiens CAMA-1 Activity nan None 10.1021/acs.jmedchem.1c00847
Homo sapiens Cellular tumor antigen p53 Potency 44668.4 nM None
Homo sapiens Cytochrome P450 19A1 IC50 530000.0 nM 10.1021/acs.jmedchem.5b01281
Homo sapiens DNA polymerase iota Potency 100000.0 nM None
Homo sapiens DU-145 IC50 15300.0 nM 10.1016/j.bmc.2021.116185
Homo sapiens Estrogen receptor alpha Activity 94.0 % 10.1021/acs.jmedchem.7b01682
Homo sapiens Estrogen receptor alpha Activity 263.0 % 10.1021/acs.jmedchem.0c02230
Homo sapiens Estrogen receptor alpha Activity nan None 10.1016/j.bmc.2019.03.042
Homo sapiens Estrogen receptor alpha Activity nan None 10.1021/acsmedchemlett.8b00414
Homo sapiens Estrogen receptor alpha DC50 0.13 nM 10.1021/acs.jmedchem.1c00847
Homo sapiens Estrogen receptor alpha EC50 nan None 10.1016/j.bmc.2019.03.042
Homo sapiens Estrogen receptor alpha Efficacy nan None 10.1021/acs.jmedchem.0c02230
Homo sapiens Estrogen receptor alpha Emax 10.0 % 10.1016/j.bmc.2019.03.042
Homo sapiens Estrogen receptor alpha Emax 62.0 % 10.1021/acs.jmedchem.1c00847
Homo sapiens Estrogen receptor alpha IC50 0.53 nM 10.1021/acsmedchemlett.6b00410
Homo sapiens Estrogen receptor alpha IC50 0.79 nM 10.1016/j.bmc.2019.03.042
Homo sapiens Estrogen receptor alpha IC50 1.36 nM 10.1021/acs.jmedchem.1c00847
Homo sapiens Estrogen receptor alpha IC50 2.1 nM 10.1016/j.bmc.2019.03.042
Homo sapiens Estrogen receptor alpha IC50 2.24 nM 10.1021/acs.jmedchem.0c02230
Homo sapiens Estrogen receptor alpha IC50 2.3 nM 10.1021/acs.jmedchem.0c02230
Homo sapiens Estrogen receptor alpha IC50 3.0 nM 10.1021/acs.jmedchem.7b01682
Homo sapiens Estrogen receptor alpha IC50 5.6 nM 10.1039/C6MD00553E
Homo sapiens Estrogen receptor alpha IC50 7.5 nM 10.1016/j.bmcl.2021.128383
Homo sapiens Estrogen receptor alpha IC50 10.0 nM 10.1016/j.bmc.2015.11.005
Homo sapiens Estrogen receptor alpha IC50 10.0 ug.mL-1 10.1016/j.ejmech.2021.113511
Homo sapiens Estrogen receptor alpha IC50 10.2 nM 10.1021/acs.jmedchem.7b01682
Homo sapiens Estrogen receptor alpha IC50 70.0 nM 10.1016/j.bmc.2015.11.005
Homo sapiens Estrogen receptor alpha Potency 28183.8 nM None
Homo sapiens Estrogen receptor alpha Potency 44668.4 nM None
Homo sapiens Estrogen receptor alpha RBA 14.7 % 10.1021/acs.jmedchem.0c02230
Homo sapiens Estrogen receptor beta IC50 1.0 nM 10.1021/acs.jmedchem.0c02230
Homo sapiens Estrogen receptor beta IC50 1.68 nM 10.1021/acs.jmedchem.0c02230
Homo sapiens Estrogen receptor beta RBA 60.7 % 10.1021/acs.jmedchem.0c02230
Homo sapiens Fibroblast Growth Rate -0.74 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast Growth Rate 0.13 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast Growth Rate 0.18 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast Growth Rate 0.22 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast Growth Rate 0.3 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast Growth Rate 0.4 None 10.6019/CHEMBL5303304
Homo sapiens Geminin Potency 3662.6 nM None
Homo sapiens Geminin Potency 11582.1 nM None
Homo sapiens Glucagon-like peptide 1 receptor Potency 7943.3 nM None
Homo sapiens Glucocorticoid receptor Potency 50118.7 nM None
Homo sapiens HEK-293T Growth Rate -0.92 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate -0.87 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate -0.68 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate -0.67 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate -0.63 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate -0.46 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate -0.33 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate -0.26 None 10.6019/CHEMBL5303304
Homo sapiens HeLa EC50 nan None 10.1021/jm500873e
Homo sapiens HepG2 IC50 relative 3900.0 nM 10.6019/EOS300108
Homo sapiens HepG2 Potency 35481.3 nM None
Homo sapiens Histone deacetylase 3 IC50 nan None 10.1016/j.bmc.2015.11.005
Homo sapiens Histone deacetylase 6 IC50 nan None 10.1016/j.bmc.2015.11.005
Homo sapiens Histone deacetylase 6 Inhibition -62.6 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 13.24 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 25118.9 nM None
Homo sapiens Ishikawa EC50 11500.0 nM 10.1021/jm500873e
Homo sapiens Ishikawa IC50 3.57 ug.mL-1 10.1016/j.bmcl.2017.04.034
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 16360.1 nM None
Homo sapiens Lysine-specific demethylase 4A Potency 56234.1 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 25118.9 nM None
Homo sapiens MCF-10A IC50 21500.0 nM 10.1021/acs.jmedchem.2c00525
Homo sapiens MCF7 Activity nan None 10.1021/acs.jmedchem.1c00847
Homo sapiens MCF7 Activity nan None 10.1021/acs.jmedchem.1c01730
Homo sapiens MCF7 Activity nan None 10.1021/acs.jmedchem.2c00008
Homo sapiens MCF7 EC50 3.5 nM 10.1021/acs.jmedchem.1c00847
Homo sapiens MCF7 EC50 7400.0 nM 10.1021/jm500873e
Homo sapiens MCF7 EC50 8800.0 nM 10.1021/jm500873e
Homo sapiens MCF7 IC50 0.95 ug.mL-1 10.1016/j.bmcl.2017.04.034
Homo sapiens MCF7 IC50 9.9 nM 10.1021/acs.jmedchem.7b01682
Homo sapiens MCF7 IC50 150.0 nM 10.1016/j.bmc.2015.11.005
Homo sapiens MCF7 IC50 670.0 nM 10.1021/acs.jmedchem.2c00525
Homo sapiens MCF7 IC50 9500.0 nM 10.1021/acs.jmedchem.8b00224
Homo sapiens MCF7 IC50 10100.0 nM 10.1016/j.ejmech.2019.03.058
Homo sapiens MCF7 IC50 15600.0 nM 10.1016/j.bmc.2021.116185
Homo sapiens MCF7 IC50 17500.0 nM 10.1021/acs.jnatprod.9b00340
Homo sapiens MCF7 IC50 nan None 10.1021/acs.jmedchem.0c02230
Homo sapiens MCF7 T/C -55.0 % 10.1021/acs.jmedchem.0c02230
Homo sapiens MDA-MB-231 EC50 7800.0 nM 10.1021/jm500873e
Homo sapiens MDA-MB-231 EC50 8000.0 nM 10.1021/jm500873e
Homo sapiens MDA-MB-231 IC50 6.51 ug.mL-1 10.1016/j.bmcl.2017.04.034
Homo sapiens MDA-MB-231 IC50 18430.0 nM 10.1021/acs.jmedchem.2c00525
Homo sapiens MDA-MB-231 IC50 nan None 10.1021/acs.jmedchem.0c02230
Homo sapiens MDA-MB-231 T/C 10.0 % 10.1021/acs.jmedchem.0c02230
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 10000.0 nM None
Homo sapiens microRNA 21 Potency 14689.2 nM None
Homo sapiens Microtubule-associated protein tau Potency 8912.5 nM None
Homo sapiens Microtubule-associated protein tau Potency 17782.8 nM None
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 35481.3 nM None
Homo sapiens Neuropeptide S receptor Potency 10000.0 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 30637.9 nM None
Homo sapiens Nuclear factor NF-kappa-B p105 subunit Potency 28183.8 nM None
Homo sapiens Peroxisome proliferator-activated receptor delta Potency 25118.9 nM None
Homo sapiens Peroxisome proliferator-activated receptor delta Potency 39810.7 nM None
Homo sapiens Peroxisome proliferator-activated receptor gamma Potency 39810.7 nM None
Homo sapiens Peroxisome proliferator-activated receptor gamma Potency 50118.7 nM None
Homo sapiens Prelamin-A/C Potency 31622.8 nM None
Homo sapiens Retinoid X receptor alpha Potency 3981.1 nM None
Homo sapiens Retinoid X receptor alpha Potency 22387.2 nM None
Homo sapiens T47D Activity nan None 10.1021/acs.jmedchem.1c00847
Homo sapiens T47D Activity nan None 10.1021/acs.jmedchem.9b01580
Homo sapiens Thyroid hormone receptor beta-1 Potency 10000.0 nM None
Homo sapiens Thyroid hormone receptor beta-1 Potency 25118.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 14581.0 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 29092.9 nM None
Homo sapiens U2OS Growth Rate -0.96 None 10.6019/CHEMBL5303304
Homo sapiens U2OS Growth Rate 0.9 None 10.6019/CHEMBL5303304
Homo sapiens Ubiquitin-conjugating enzyme E2 N IC50 20000.0 nM None
Homo sapiens Vitamin D receptor Potency 50118.7 nM None
Influenza A virus Nonstructural protein 1 Potency 11220.2 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 15848.9 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 35481.3 nM None
Rattus norvegicus Nuclear receptor subfamily 1 group I member 2 Potency 31622.8 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 0.28 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 12.96 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.31 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.24 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.19 % 10.21203/rs.3.rs-23951/v1
None ADMET CL 14.0 mL.min-1.kg-1 10.1021/acs.jmedchem.1c00847
None ADMET CL 32.0 mL.min-1.kg-1 10.1021/acs.jmedchem.1c00847
None ADMET CL nan None 10.1021/acs.jmedchem.1c00847
None ADMET IC50 10000.0 nM 10.1021/jm500873e
None ADMET Ratio IC50 32.09 None 10.1021/acs.jmedchem.2c00525
None ADMET Selectivity Index 1.0 None 10.1016/j.bmc.2021.116185
None Molecular identity unknown Potency 7943.3 nM None
None Molecular identity unknown Potency 25118.9 nM None
None NON-PROTEIN TARGET EC50 10000.0 nM 10.1021/jm500873e
None NON-PROTEIN TARGET IC50 3.4 nM 10.1021/acsmedchemlett.6b00410
None NON-PROTEIN TARGET IC50 20000.0 nM 10.1021/acsmedchemlett.6b00410
None NON-PROTEIN TARGET Ratio IC50/EC50 1.28 None 10.1021/jm500873e
None NON-PROTEIN TARGET Ratio IC50/EC50 13.5 None 10.1021/jm500873e
None No relevant target LogD 4.0 None 10.1021/acs.jmedchem.1c00847
None No relevant target Solubility 31000.0 nM 10.1021/acs.jmedchem.1c00847
None Unchecked AbsAC40_uM 2.41 uM None
None Unchecked Activity 10.0 % 10.1021/acs.jmedchem.5b01677
None Unchecked Activity nan None 10.1021/acs.jmedchem.1c00847
None Unchecked Activity nan None 10.1021/acs.jmedchem.2c00525
None Unchecked CC50 16615.0 nM None
None Unchecked IC50 8758.0 nM None
None Unchecked IC50 22220.0 nM 10.1021/acs.jmedchem.2c00525
None Unchecked IC50 22490.0 nM None
None Unchecked IC50 26520.0 nM None
None Unchecked IC50 100000.0 nM 10.1021/acs.jmedchem.8b00224
None Unchecked IC50 nan None 10.1021/acs.jmedchem.0c02230
None Unchecked Inhibition 21.51 % 10.1021/acs.jmedchem.8b00224
None Unchecked Potency 2818.4 nM None
None Unchecked Potency 11220.2 nM None
None Unchecked Potency 18356.4 nM None
None Unchecked Potency 20596.2 nM None
None Unchecked Potency 35481.3 nM None
None Unchecked Ratio 2.0 None 10.1021/acs.jmedchem.2c00008
None Unchecked T/C -57.0 % 10.1021/acs.jmedchem.0c02230

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT006666 CC/C(=C(\c1ccc(O)cc1)c1ccc(OCCN(C)C)cc1)c1ccccc1.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>CC/C(=C(/c1ccc(OCCN(C)C)cc1)c1ccc(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)cc1)c1ccccc1 enzymemap_34581
AKRT006667 CC/C(=C(\c1ccc(O)cc1)c1ccc(OCCN(C)C)cc1)c1ccccc1>>CC/C(=C(/c1ccc(OCCN(C)C)cc1)c1ccc(OS(=O)(=O)O)cc1)c1ccccc1 enzymemap_49875
AKRT006671 CC/C(=C(\c1ccccc1)c1ccc(OCCN(C)C)cc1)c1ccccc1>>CC/C(=C(\c1ccc(O)cc1)c1ccc(OCCN(C)C)cc1)c1ccccc1 R08267