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Compound Detail

CHEMBL174984

TRETOQUINOL
🧪 Phase II
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🧪 Phase II
COc1cc(C[C@@H]2NCCc3cc(O)c(O)cc32)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL174984
Name TRETOQUINOL
Phase Phase II
Structure Type MOL
InChI Key RGVPOXRFEPSFGH-AWEZNQCLSA-N

Known Names

(-)-tretoquinol Dl-trimetoquinol Inolin NSC-288748 Racemic-trimetoquinol RO-07-5965 S-(-)-tretoquinol Tretoquinol Tretoquinol hydrochloride Tretoquinol hydrochloride hydrate Tretoquinol, (-)- Trimetoquinol hydrochloride
11
Targets
27
Activities
3
Assay Types
0
PK Parameters
20
Publications
12
Known Names
1
Indications

Molecular Properties

345.4
MW (Da)
2.55
ALogP
6
HBA
3
HBD
80.2
PSA (Ų)
0.72
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Extended Properties

Molecular Formula C19H23NO5
MW 345.40
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 1.18

Indications

Lung Diseases, Obstructive

ATC Classification

R03AC09
tretoquinol
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R03CC09
tretoquinol
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Activity Summary

Ki 12 meas. best 7.36
IC50 9 meas. best 8.21
EC50 6 meas. best 8.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-3 adrenergic receptor
CHEMBL246
 EC50 8.77 8.77 1.7 1
Beta-2 adrenergic receptor
CHEMBL210
 EC50 8.46 8.46 3.5 1
Beta-1 adrenergic receptor
CHEMBL213
 IC50 8.21 8.21 6.1 1
Beta-2 adrenergic receptor
CHEMBL210
 IC50 8.21 8.21 6.1 1
Beta-1 adrenergic receptor
CHEMBL213
 EC50 7.85 7.85 14.0 1
Beta-2 adrenergic receptor
CHEMBL5414
 EC50 7.58 7.58 26.3 1
Adrenergic receptor beta
CHEMBL2094118
 EC50 7.51 7.51 31.0 1
Beta-2 adrenergic receptor
CHEMBL210
 Ki 7.36 7.36 43.6 2
Beta-2 adrenergic receptor
CHEMBL5414
 Ki 7.31 7.31 49.0 1
Beta-1 adrenergic receptor
CHEMBL5471
 Ki 7.06 7.06 87.1 1
Adrenergic receptor beta
CHEMBL2095166
 Ki 7.0 7.0 100.0 1
Thromboxane A2 receptor
CHEMBL2069
 Ki 6.79 6.775 162.2 2
Beta-1 adrenergic receptor
CHEMBL5471
 EC50 6.76 6.76 173.8 1
Thromboxane A2 receptor
CHEMBL2069
 IC50 6.55 6.45 281.8 2
Beta-1 adrenergic receptor
CHEMBL213
 Ki 6.49 6.49 323.6 2
Homo sapiens
CHEMBL372
 IC50 5.94 5.076 1148.2 5
Beta-3 adrenergic receptor
CHEMBL246
 Ki 5.43 5.43 3715.3 1
Dopamine receptor
CHEMBL2093868
 Ki 5.3 5.3 5000.0 1
Adrenergic receptor alpha
CHEMBL2094111
 Ki 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-3 adrenergic receptor EC50 = 1.7 nM 8.77 Inhibitory activity against human beta-3 adrenergic receptor (AR) 11055339
Beta-2 adrenergic receptor EC50 = 3.5 nM 8.46 Compound was evaluated for its inhibitory activity against human beta-2 adrenerg... 11055339
Beta-1 adrenergic receptor IC50 = 6.1 nM 8.21 Compound was evaluated for its inhibitory activity against CHO cells expressing ... 11055339
Beta-2 adrenergic receptor IC50 = 6.1 nM 8.21 Compound was evaluated for its inhibitory activity against CHO cells expressing ... 11055339
Beta-1 adrenergic receptor EC50 = 14.0 nM 7.85 Compound was evaluated for its inhibitory activity against human Beta-1 adrenerg... 11055339
Beta-2 adrenergic receptor EC50 = 26.3 nM 7.58 Inhibitory activity against Beta-2 adrenergic receptor in guinea pig trachea aft... 1346651
Adrenergic receptor beta EC50 = 31.0 nM 7.51 Compound was tested for its intrinsic activity against beta adrenergic receptor ... 2878080
Beta-2 adrenergic receptor Ki = 43.65 nM 7.36 Binding Affinity against human beta-2 adrenergic receptor expressed in Chinese h... 10377236
Beta-2 adrenergic receptor Ki = 43.65 nM 7.36 Binding affinity for human Beta-2 adrenergic receptor expressed in CHO cells by ... 8809159
Beta-2 adrenergic receptor Ki = 48.98 nM 7.31 Binding affinity against Beta-2 adrenergic receptor in guinea pig lung membranes 1346651
Beta-1 adrenergic receptor Ki = 87.1 nM 7.06 Binding affinity against Beta-1 adrenergic receptor in guinea pig left ventricle 1346651
Adrenergic receptor beta Ki = 100.0 nM 7.0 Inhibition of [3H]dihydroalprenolol binding to Beta adrenergic receptor from rat... 6248642
Thromboxane A2 receptor Ki = 162.18 nM 6.79 Binding affinity for human Platelet Thromboxane A2 / Prostaglandin (TP), by radi... 8809159
Beta-1 adrenergic receptor EC50 = 173.78 nM 6.76 Inhibitory activity against Beta-1 adrenergic receptor in guinea pig atria after... 1346651
Thromboxane A2 receptor Ki = 173.78 nM 6.76 Inhibitory concentration against radioligand [3H]SQ-29,548 (5 nM) binding to TP ... 9016331
Thromboxane A2 receptor IC50 = 281.84 nM 6.55 Inhibitory activity against U-46,619-induced responses in human platelet aggrega... 1346651
Beta-1 adrenergic receptor Ki = 323.59 nM 6.49 Binding affinity for human Beta-1 adrenergic receptor expressed in CHO cells by ... 8809159
Beta-1 adrenergic receptor Ki = 323.59 nM 6.49 Binding Affinity against human Beta-1 adrenergic receptor expressed in Chinese h... 10377236
Thromboxane A2 receptor IC50 = 446.68 nM 6.35 Inhibitory concentration against radioligand [3H]SQ-29,548 (5 nM) binding to TP ... 9016331
Homo sapiens IC50 = 1148.15 nM 5.94 Inhibitory activity against U-46,619-induced (1 uM) human platelet activation (a... 9016331

Literature References

PubMed DOI Target Context # Activities
31479 10.1021/jm00209a019 Adrenergic receptor beta 6
31479 10.1021/jm00209a019 Unchecked 4
1346651 10.1021/jm00081a007 Beta-2 adrenergic receptor 4
1346651 10.1021/jm00081a007 Beta-1 adrenergic receptor 4
9016331 10.1021/jm950896w Beta-2 adrenergic receptor 3
10377236 10.1021/jm990012z Beta-3 adrenergic receptor 3
10377236 10.1021/jm990012z Beta-2 adrenergic receptor 3
10377236 10.1021/jm990012z Beta-1 adrenergic receptor 3
11055339 10.1016/s0960-894x(00)00459-5 Beta-2 adrenergic receptor 3
11055339 10.1016/s0960-894x(00)00459-5 Beta-1 adrenergic receptor 3
2878080 10.1021/jm00161a039 No relevant target 3
2869145 10.1021/jm00152a003 Homo sapiens 3
9016331 10.1021/jm950896w Beta-1 adrenergic receptor 3
9016331 10.1021/jm950896w Homo sapiens 3
950642 10.1021/jm00228a005 Unchecked 3
6120236 10.1021/jm00140a011 Beta-2 adrenergic receptor 2
8809159 10.1021/jm960208o Thromboxane A2 receptor 2
11055339 10.1016/s0960-894x(00)00459-5 Beta-3 adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
10691685 10.1021/jm990463j Beta-2 adrenergic receptor 2

Data from ChEMBL 36 via Core Engine