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Compound Detail

CHEMBL193482

ESTRIOL
💊 Approved Drug
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💊 Approved Drug
C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1C[C@@H](O)[C@@H]2O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL193482
Name ESTRIOL
Phase Approved
Structure Type MOL
InChI Key PROQIPRRNZUXQM-ZXXIGWHRSA-N
Therapeutic ✓ Yes

Known Names

16.alpha.,17.beta.-estriol 16.ALPHA.-HYDROXYESTRADIOL Aacifemine Colpogyn Estriol Estriol acetate benzoate Estriol propionate Estriol succinate Gynest Incurin NSC-12169 Oestriol +5 more
12
Targets
17
Activities
4
Assay Types
2
PK Parameters
20
Publications
17
Known Names
6
Indications
1
Mechanisms

Molecular Properties

288.4
MW (Da)
2.58
ALogP
3
HBA
3
HBD
60.7
PSA (Ų)
0.69
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2000
Availability Unknown
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product
USAN Stem estr-

Extended Properties

Molecular Formula C18H24O3
MW 288.39
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness 2.51

Mechanism of Action

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

Indications

Atrophic Vaginitis Menopause Multiple Sclerosis, Chronic Progressive Multiple Sclerosis, Chronic Progressive Multiple Sclerosis, Relapsing-Remitting Pregnancy

ATC Classification

G03CA04
estriol
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G03CC06
estriol
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Activity Summary

IC50 6 meas. best 8.77
Ki 5 meas. best 9.32
EC50 4 meas. best 10.32
Kd 2 meas. best 6.63

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 EC50 10.32 10.32 0.0 1
Estrogen receptor beta
CHEMBL242
 EC50 9.9 9.9 0.1 1
Estrogen receptor
CHEMBL206
 Ki 9.32 9.32 0.5 1
Estrogen receptor
CHEMBL206
 IC50 8.77 8.77 1.7 1
Estrogen receptor
CHEMBL206
 EC50 8.7 8.7 2.0 1
Sex hormone-binding globulin
CHEMBL3305
 Kd 6.63 6.63 234.4 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 5.26 5.26 5491.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL4358
 IC50 5.06 5.06 8635.0 1
Solute carrier organic anion transporter family member 1A1
CHEMBL1781859
 Ki 5.01 5.01 9800.0 1
Corticosteroid-binding globulin
CHEMBL2421
 Ki 5.0 5.0 10000.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 4.99 4.99 10336.0 1
Glucocorticoid receptor
CHEMBL2034
 Ki 4.75 4.75 17884.0 1
Alpha-synuclein
CHEMBL6152
 IC50 4.7 4.7 20100.0 1
Glucocorticoid receptor
CHEMBL2034
 IC50 4.41 4.41 39345.0 1
Olfactory receptor 51E2
CHEMBL4523454
 EC50 4.28 4.28 53000.0 1
Sterol 14alpha-demethylase
CHEMBL5090
 Kd 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 614000000.0 M-1 -
Ka 7000000000.0 M-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 EC50 = 0.0483 nM 10.32 Growth response in cultures of MCF-7 (human breast cancer cell line) cells 9357533
Estrogen receptor beta EC50 = 0.1259 nM 9.9 Agonist activity at ER-beta (unknown origin) transfected in HEK293T cells after ... -
Estrogen receptor Ki = 0.483 nM 9.32 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Estrogen receptor IC50 = 1.691 nM 8.77 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Estrogen receptor EC50 = 1.995 nM 8.7 Agonist activity at ER-alpha (unknown origin) transfected in HEK293T cells after... -
Sex hormone-binding globulin Kd = 234.42 nM 6.63 Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding gl... 18330978
Sodium-dependent serotonin transporter Ki = 5491.0 nM 5.26 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Polyunsaturated fatty acid lipoxygenase ALOX15 IC50 = 8635.0 nM 5.06 DRUGMATRIX: Lipoxygenase 15-LO enzyme inhibition (substrate: Linoleic acid) -
Solute carrier organic anion transporter family member 1A1 Ki = 9800.0 nM 5.01 TP_TRANSPORTER: inhibition of E217betaG uptake in Oatp1-expressing HeLa cells 8779894
Corticosteroid-binding globulin Ki = 10000.0 nM 5.0 Binding affinity to human CBG receptor (corticosteroid-binding globulins) 15139751
Sodium-dependent serotonin transporter IC50 = 10336.0 nM 4.99 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Glucocorticoid receptor Ki = 17884.0 nM 4.75 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Alpha-synuclein IC50 = 20100.0 nM 4.7 Inhibition of alpha-synuclein aggregation (unknown origin) incubated for 8 days ... 30743095
Glucocorticoid receptor IC50 = 39345.0 nM 4.41 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Olfactory receptor 51E2 EC50 = 53000.0 nM 4.28 Agonist activity at PSGR/OR51E2 (unknown origin) expressed in human Hana3A cells... -
Sterol 14alpha-demethylase Kd = 100000.0 nM 4.0 Binding affinity to Mycobacterium tuberculosis His4-tagged recombinant CYP51 sub... 17846131

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 523
23288867 10.1124/dmd.112.049072 ADMET 6
23288867 10.1124/dmd.112.049072 UDP-glucuronosyltransferase 1A10 5
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B4 4
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B7 4
23288867 10.1124/dmd.112.049072 Liver microsome 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 1A1 3
23288867 10.1124/dmd.112.049072 UDP-glucuronosyltransferase 2B7 3
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 1-6 3
- 10.1039/C3MD00194F Estrogen receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 1A9 3
- 10.1039/C3MD00194F Estrogen receptor beta 3
22931300 10.1021/tx300075j Liver microsomes 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
19772289 10.1021/jm900921c 3-keto-steroid reductase/17-beta-hydroxysteroid dehydrogenase 7 2
7629815 10.1021/jm00014a028 Estrogen receptor 2
9554872 10.1021/jm970725m Nucleic Acid 2
7853335 10.1021/jm00003a005 Estrogen receptor 2

Data from ChEMBL 36 via Core Engine