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Compound Detail

CHEMBL2386285

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CC/C(=C(/c1ccc(O)cc1)c1ccc(OCCN)cc1)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2386285
Phase Preclinical
Structure Type MOL
InChI Key YCQBLTPGQSYLHD-WCWDXBQESA-N
7
Targets
19
Activities
3
Assay Types
4
PK Parameters
15
Publications
0
Known Names

Molecular Properties

359.5
MW (Da)
5.10
ALogP
3
HBA
2
HBD
55.5
PSA (Ų)
0.58
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H25NO2
MW 359.47
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness 0.15

Activity Summary

IC50 8 meas. best 7.12
EC50 6 meas. best 7.57
Ki 5 meas. best 7.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor
CHEMBL206
 EC50 7.57 7.3433 27.0 3
Estrogen receptor beta
CHEMBL242
 EC50 7.45 7.2233 35.2 3
Aromatase
CHEMBL1978
 Ki 7.32 7.32 48.0 1
Aromatase
CHEMBL1978
 IC50 7.12 7.07 76.8 4
Cytochrome P450 1A2
CHEMBL3356
 Ki 7.12 7.12 76.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 6.68 6.68 207.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 6.54 6.54 285.0 1
Cytochrome P450 3A4
CHEMBL340
 Ki 6.43 6.43 375.0 1
Cytochrome P450 3A5
CHEMBL3019
 IC50 6.14 6.14 723.0 1
Cytochrome P450 3A5
CHEMBL3019
 Ki 6.08 6.08 829.0 1
Cytochrome P450 2A6
CHEMBL5282
 Ki 5.66 5.66 2180.0 1
Cytochrome P450 2A6
CHEMBL5282
 IC50 5.2 5.2 6370.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 5.8 ng.hr.mL-1 Mus musculus
Cmax 1947.31 nM Mus musculus
T1/2 21.4 hr Mus musculus
Tmax 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor EC50 = 27.0 nM 7.57 Displacement of fluorescein-labeled ES2 from human recombinant ERalpha receptor ... 25751283
Estrogen receptor beta EC50 = 35.2 nM 7.45 Displacement of fluorescein-labeled ES2 from human recombinant ERbeta receptor a... 25751283
Aromatase Ki = 48.0 nM 7.32 Inhibition of human recombinant microsomal aromatase using 7-methoxy-4-trifluoro... 23731360
Estrogen receptor EC50 = 58.7 nM 7.23 Displacement of fluorescent ES2 from human recombinant ERalpha after 2 hrs by fl... 23731360
Estrogen receptor EC50 = 58.7 nM 7.23 Displacement of fluorescent ES2 from recombinant human ERalpha after 2 hrs in ab... 27647367
Aromatase IC50 = 76.8 nM 7.12 Inhibition of human recombinant microsomal aromatase-mediated 7-methoxy-4-triflu... 23731360
Aromatase IC50 = 76.8 nM 7.12 Inhibition of recombinant human microsomal CYP19 using MFC as substrate measured... 27647367
Cytochrome P450 1A2 Ki = 76.0 nM 7.12 Inhibition of human recombinant CYP1A2 assessed as metabolism of 3-cyano-7-ethox... 25751283
Estrogen receptor beta EC50 = 78.5 nM 7.11 Displacement of fluorescent ES2 from human recombinant ERbeta after 2 hrs by flu... 23731360
Estrogen receptor beta EC50 = 78.5 nM 7.11 Displacement of fluorescent ES2 from recombinant human ERbeta after 2 hrs in abs... 27647367
Aromatase IC50 = 90.0 nM 7.05 Inhibition of human recombinant placental aromatase 23731360
Aromatase IC50 = 102.0 nM 6.99 Inhibition of human recombinant aromatase using 7-methoxy-trifluoromethylcoumari... 25751283
Cytochrome P450 1A2 IC50 = 207.0 nM 6.68 Inhibition of human recombinant CYP1A2 assessed as metabolism of 3-cyano-7-ethox... 25751283
Cytochrome P450 3A4 IC50 = 285.0 nM 6.54 Inhibition of human recombinant CYP3A4 assessed as metabolism of 7-benzyloxy-4-t... 25751283
Cytochrome P450 3A4 Ki = 375.0 nM 6.43 Inhibition of human recombinant CYP3A4 assessed as metabolism of 7-benzyloxy-4-t... 25751283
Cytochrome P450 3A5 IC50 = 723.0 nM 6.14 Inhibition of human recombinant CYP3A5 assessed as metabolism of 7-benzyloxy-4-t... 25751283
Cytochrome P450 3A5 Ki = 829.0 nM 6.08 Inhibition of human recombinant CYP3A5 assessed as metabolism of 7-benzyloxy-4-t... 25751283
Cytochrome P450 2A6 Ki = 2180.0 nM 5.66 Inhibition of human recombinant CYP2A6 assessed as metabolism of coumarin to 7-h... 25751283
Cytochrome P450 2A6 IC50 = 6370.0 nM 5.2 Inhibition of human recombinant CYP2A6 assessed as metabolism of coumarin to 7-h... 25751283

Literature References

PubMed DOI Target Context # Activities
23731360 10.1021/jm400364h Mus musculus 7
23731360 10.1021/jm400364h Aromatase 3
25751283 10.1021/jm501218e Cytochrome P450 1A2 2
25751283 10.1021/jm501218e Cytochrome P450 3A5 2
25751283 10.1021/jm501218e Cytochrome P450 3A4 2
25751283 10.1021/jm501218e Cytochrome P450 2D6 2
25751283 10.1021/jm501218e Cytochrome P450 2A6 2
25751283 10.1021/jm501218e Estrogen receptor 2
27647367 10.1016/j.bmc.2016.08.064 Aromatase 2
23731360 10.1021/jm400364h Estrogen receptor beta 1
23731360 10.1021/jm400364h Estrogen receptor 1
25751283 10.1021/jm501218e Aromatase 1
25751283 10.1021/jm501218e Estrogen receptor beta 1
27647367 10.1016/j.bmc.2016.08.064 Estrogen receptor 1
27647367 10.1016/j.bmc.2016.08.064 Estrogen receptor beta 1

Data from ChEMBL 36 via Core Engine