Compound Detail

CHEMBL954

ENCLOMIPHENE

🧪 Phase III

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🧪 Phase III

CCN(CC)CCOc1ccc(/C(=C(/Cl)c2ccccc2)c2ccccc2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL954
Name	ENCLOMIPHENE
Phase	Phase III
Structure Type	MOL
InChI Key	GKIRPKYJQBWNGO-OCEACIFDSA-N
Active Moiety	CHEMBL1056

Known Names

Cisclomiphene Clomiphene trans-form Enclomifene Enclomifeno Enclomiphene ICI-46476 ISOMER B ISOMER-B RMI 16,289 Rmi-16,289 RMI-16289

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

406.0

MW (Da)

6.56

ALogP

HBA

HBD

12.5

PSA (Å²)

0.37

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product Prodrug

USAN Year

1974

Extended Properties

Molecular Formula	C26H28ClNO
MW	405.97
Aromatic Rings	3
Heavy Atoms	29
NP-Likeness	-0.67

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Estrogen receptor alpha modulator	MODULATOR	Estrogen receptor	✓	✓

Indications

Hypogonadism Obesity

Activity Summary

IC50 39 meas. best 8.34

Ki 30 meas. best 9.0

EC50 1 meas. best 5.37

Kd 1 meas. best 4.51

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase CHEMBL4931	Ki	9.0	9.0	1.0	1
Estrogen receptor CHEMBL206	Ki	8.88	8.88	1.3	1
Estrogen receptor CHEMBL206	IC50	8.34	8.34	4.6	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	8.1	8.01	8.0	2
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	7.54	7.54	29.0	1
Unchecked CHEMBL612545	Ki	7.52	6.404	30.0	5
Unchecked CHEMBL612545	IC50	7.31	6.304	49.0	5
C-8 sterol isomerase ERG2 CHEMBL3224	Ki	6.8	6.8	160.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.67	6.67	215.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	6.64	6.64	230.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.47	6.47	339.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.46	6.46	351.0	1
Prostaglandin G/H synthase 1 CHEMBL221	IC50	6.46	6.46	346.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	6.41	6.41	392.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	6.36	6.36	439.0	1
D(3) dopamine receptor CHEMBL234	Ki	6.35	6.35	448.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	6.21	6.21	623.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	6.2	6.2	638.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.18	6.18	666.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.15	6.15	707.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.14	6.14	721.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	6.11	6.11	784.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	6.07	6.07	855.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	6.06	6.06	862.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.06	6.06	867.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.03	6.03	945.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	6.03	6.03	936.0	1
Epidermal growth factor receptor CHEMBL203	IC50	5.98	5.98	1050.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	5.9	5.9	1272.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	5.9	5.9	1272.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	5.89	5.89	1290.0	1
D(3) dopamine receptor CHEMBL234	IC50	5.88	5.88	1319.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	5.87	5.87	1363.0	1
Plasmodium falciparum CHEMBL364	IC50	5.86	5.86	1370.0	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	5.83	5.83	1482.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	5.82	5.82	1522.0	1
Substance-K receptor CHEMBL2327	Ki	5.82	5.82	1508.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	5.8	5.8	1578.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	5.79	5.79	1628.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	5.78	5.78	1651.0	1
Receptor tyrosine-protein kinase erbB-2 CHEMBL1824	IC50	5.78	5.78	1669.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	5.75	5.75	1771.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	5.68	5.68	2071.0	1
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	5.6	5.6	2513.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	5.6	5.6	2529.0	1
Adenosine receptor A3 CHEMBL256	Ki	5.52	5.52	3024.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	5.48	5.48	3308.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	5.44	5.44	3628.0	1
Rev responsive element (RRE) RNA CHEMBL613297	IC50	5.43	5.43	3700.0	1
Human immunodeficiency virus 1 CHEMBL378	EC50	5.37	5.37	4300.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	Ki	=	1.0	nM	9.0	Affinity for human EMP expressed in ERG2 deficient strain of Saccharomyces cerev...	16033255
Estrogen receptor	Ki	=	1.304	nM	8.88	DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol)	-
Estrogen receptor	IC50	=	4.564	nM	8.34	DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol)	-
Sigma non-opioid intracellular receptor 1	Ki	=	8.0	nM	8.1	Affinity for sigma receptor type 1 of guinea pig using [3H]ifenprodil or (+)-[3H...	16033255
Sigma non-opioid intracellular receptor 1	Ki	=	12.0	nM	7.92	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Sigma non-opioid intracellular receptor 1	IC50	=	29.0	nM	7.54	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Unchecked	Ki	=	30.0	nM	7.52	DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil)	-
Unchecked	IC50	=	49.0	nM	7.31	DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil)	-
C-8 sterol isomerase ERG2	Ki	=	160.0	nM	6.8	Affinity for ERG2 of Saccharomyces cerevisiae using [3H]ifenprodil or (+)-[3H]pe...	16033255
Alpha-2C adrenergic receptor	Ki	=	215.0	nM	6.67	DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912)	-
Muscarinic acetylcholine receptor M4	Ki	=	230.0	nM	6.64	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Sodium-dependent serotonin transporter	Ki	=	339.0	nM	6.47	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
Prostaglandin G/H synthase 1	IC50	=	346.0	nM	6.46	DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid)	-
Alpha-2A adrenergic receptor	Ki	=	351.0	nM	6.46	DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912)	-
Muscarinic acetylcholine receptor M1	Ki	=	392.0	nM	6.41	DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M3	Ki	=	439.0	nM	6.36	DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
D(3) dopamine receptor	Ki	=	448.0	nM	6.35	DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone)	-
Unchecked	Ki	=	580.0	nM	6.24	DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox...	-
Sodium-dependent dopamine transporter	Ki	=	623.0	nM	6.21	DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55)	-
Unchecked	IC50	=	636.0	nM	6.2	DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	415
16472241	10.2174/1570163043334794	Hepatotoxicity	18
34473495	10.1021/acs.jmedchem.1c00941	Staphylococcus aureus	5
-	10.6019/CHEMBL3392926	NON-PROTEIN TARGET	2
-	10.6019/CHEMBL3392926	Leishmania donovani	2
38318365	10.1016/j.isci.2024.108907	Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	1
4009597	10.1021/jm00383a011	Calf thymus DNA	1
32832035	10.1021/acsmedchemlett.0c00298	Unchecked	1
31534649	10.1039/C9MD00195F	Rev responsive element (RRE) RNA	1
31534649	10.1039/C9MD00195F	Human immunodeficiency virus 1	1
-	10.6019/CHEMBL3392926	Plasmodium falciparum	1
-	10.6019/CHEMBL3392926	Trypanosoma brucei rhodesiense	1
-	10.6019/CHEMBL3392926	Trypanosoma cruzi	1
-	10.6019/CHEMBL3301361	No relevant target	1
16033255	10.1021/jm049073+	C-8 sterol isomerase ERG2	1
16033255	10.1021/jm049073+	Sigma non-opioid intracellular receptor 1	1
16033255	10.1021/jm049073+	3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	1
4009597	10.1021/jm00383a011	Estrogen receptor	1

Data from ChEMBL 36 via Core Engine