Compound Detail

CHEMBL299613

2-METHOXYESTRADIOL

🧪 Phase II

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🧪 Phase II

COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL299613
Name	2-METHOXYESTRADIOL
Phase	Phase II
Structure Type	MOL
InChI Key	CQOQDQWUFQDJMK-SSTWWWIQSA-N

Known Names

2-methoxyestradiol 2-methoxyoestradiol NSC-659853

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

302.4

MW (Da)

3.62

ALogP

HBA

HBD

49.7

PSA (Å²)

0.83

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem

-estr-

Extended Properties

Molecular Formula	C19H26O3
MW	302.41
Aromatic Rings	1
Heavy Atoms	22
NP-Likeness	2.16

Indications

Multiple Myeloma Neoplasms

Activity Summary

IC50 59 meas. best 6.6

Ki 2 meas. best 4.44

Kd 1 meas. best 9.08

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sex hormone-binding globulin CHEMBL3305	Kd	9.08	9.08	0.8	1
MDA-MB-231 CHEMBL400	IC50	6.6	6.0167	250.0	6
LNCaP CHEMBL612518	IC50	6.3	6.3	500.0	1
HUVEC CHEMBL613979	IC50	6.28	5.9586	523.0	7
HeLa CHEMBL399	IC50	6.23	5.84	586.0	3
K562 CHEMBL385	IC50	6.1	6.1	800.0	1
MCF7 CHEMBL387	IC50	6.08	5.64	842.0	3
SK-OV-3 CHEMBL614925	IC50	6.06	5.4933	867.0	3
HL-60 CHEMBL383	IC50	6.05	5.76	900.0	2
MDA-MB-435 CHEMBL614697	IC50	6.0	6.0	1000.0	1
A549 CHEMBL392	IC50	5.96	5.96	1100.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.92	5.5425	1200.0	4
Tubulin CHEMBL2111464	IC50	5.85	5.85	1400.0	1
SK-N-SH CHEMBL614924	IC50	5.8	5.8	1600.0	1
Tubulin CHEMBL2111354	IC50	5.66	5.66	2200.0	1
HepG2 CHEMBL395	IC50	5.64	5.3	2300.0	2
PC-3 CHEMBL390	IC50	5.58	5.245	2650.0	2
Tubulin beta chain CHEMBL3394	IC50	5.54	5.41	2900.0	2
U-937 CHEMBL612794	IC50	5.54	5.54	2910.0	1
Tubulin CHEMBL2094134	IC50	5.51	4.995	3100.0	4
B16 CHEMBL381	IC50	5.47	5.47	3400.0	1
MGC-803 CHEMBL3706566	IC50	5.4	5.4	4000.0	1
ECa-109 cell line CHEMBL614668	IC50	5.39	5.39	4100.0	1
HEK-293T CHEMBL3706568	IC50	5.34	5.34	4600.0	1
Unchecked CHEMBL612545	IC50	5.16	4.7333	7000.0	3
SMMC-7721 CHEMBL613831	IC50	5.08	5.08	8400.0	1
Ishikawa CHEMBL614649	IC50	5.05	5.05	8960.0	1
Plasmodium falciparum CHEMBL364	IC50	4.9	4.9	12589.2	1
Aromatase CHEMBL1978	IC50	4.7	4.7	19998.6	1
T47D CHEMBL614361	IC50	4.6	4.6	25200.0	1
Cytochrome P450 1B1 CHEMBL4878	Ki	4.44	4.44	36000.0	1
Cytochrome P450 1A1 CHEMBL2231	Ki	4.06	4.06	88000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	42.94	ng.hr.mL-1	Mus musculus
Cmax	294.0	nM	Mus musculus
T1/2	0.3	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sex hormone-binding globulin	Kd	=	0.8318	nM	9.08	Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding gl...	18330978
MDA-MB-231	IC50	=	250.0	nM	6.6	Inhibition of estrogen receptor negative MDA-MB 231 breast cancer cell prolifera...	9357519
LNCaP	IC50	=	500.0	nM	6.3	Antiproliferative activity against human LNCaP cell line	16650989
HUVEC	IC50	=	523.0	nM	6.28	Antiangiogenic activity against HUVEC cells assessed as inhibition of proliferat...	18260615
HeLa	IC50	=	586.0	nM	6.23	Antiproliferative activity against human HeLa cells expressing tubulin 3beta by ...	20973488
HeLa	IC50	=	608.0	nM	6.22	Antiproliferative activity against human HeLa cells by sulforhodamine B assay	20973488
HUVEC	IC50	=	680.0	nM	6.17	Antiangiogenic activity against HUVEC assessed as growth inhibition after 48 hrs...	19782564
HUVEC	IC50	=	680.0	nM	6.17	Antiangiogenic activity in HUVEC assessed as inhibition of cell proliferation	19782568
MDA-MB-231	IC50	=	790.0	nM	6.1	Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by WST1 a...	19782564
MDA-MB-231	IC50	=	790.0	nM	6.1	Antiproliferative activity against human MDA-MB-231 cells	19782568
K562	IC50	=	800.0	nM	6.1	Anticancer activity against human K562 cells assessed as cell growth inhibition ...	25108078
HUVEC	IC50	=	840.0	nM	6.08	Growth inhibitory concentration against MDA-MB-231 cancer cell line	15456256
MCF7	IC50	=	842.0	nM	6.08	Antiproliferative activity against human MCF7 cells after 72 hrs by crystal viol...	20334421
HUVEC	IC50	=	840.0	nM	6.08	Antiangiogenic activity against HUVECs by Brdu incorporation assay	19762246
HUVEC	IC50	=	840.0	nM	6.08	Antiproliferative activity against human HUVECs after 48 hrs	17910916
SK-OV-3	IC50	=	867.0	nM	6.06	Antiproliferative activity against human SKOV3 cells by sulforhodamine B assay	20973488
HL-60	IC50	=	900.0	nM	6.05	Cytotoxicity against vincristine-resistant human HL60 cells after 72 hrs MTS ass...	20411988
MDA-MB-231	IC50	=	1000.0	nM	6.0	Antiproliferative activity against human MDA-MB-231 cells after 48 hrs	17910916
MDA-MB-231	IC50	=	1000.0	nM	6.0	Growth inhibitory concentration against HUVEC cancer cell line	15456256
MDA-MB-435	IC50	=	1000.0	nM	6.0	Antiproliferative activity against human MDA-MB-435 cells by Brdu incorporation ...	19762246

Literature References

PubMed	DOI	Target Context	# Activities
18052315	10.1021/jm070639e	Plasma	15
12361402	10.1021/jm020218r	Homo sapiens	8
12672229	10.1021/jm034007d	HUVEC	6
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
31102934	10.1016/j.ejmech.2019.04.071	ADMET	5
33691794	10.1186/s13148-021-01037-1	A549	4
25108078	10.1016/j.ejmech.2014.08.002	NON-PROTEIN TARGET	3
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	3
10882369	10.1021/jm0001119	Tubulin	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
19762246	10.1016/j.bmc.2009.08.038	Liver microsomes	3
20411988	10.1021/jm901805m	HL-60	3
20973488	10.1021/jm101010n	HeLa	3
19782564	10.1016/j.bmcl.2009.08.020	Mus musculus	3
20973488	10.1021/jm101010n	SK-OV-3	3
22305612	10.1016/j.ejmech.2012.01.033	Hepatocyte	2
31102934	10.1016/j.ejmech.2019.04.071	MGC-803	2
-	10.1016/S0960-894X(00)80369-8	Mus musculus	2
20225862	10.1021/jm9018806	Unchecked	2
28810190	10.1016/j.ejmech.2017.08.016	Ishikawa	2

Data from ChEMBL 36 via Core Engine