17β-estradiol   Click here for help

GtoPdb Ligand ID: 1013

Abbreviated name: E2
Synonyms: estrogen | oestrodiol | oestrogen
Approved drug PDB Ligand
17β-estradiol is an approved drug (FDA (1954, prior history unavailable))
Compound class: Metabolite or derivative
Comment: 17β-estradiol is the predominant form of circulating estrogen and is the endogenous agonist of the estrogen receptor α. In pre-menopausal women 17β-estradiol is mainly produced by the ovaries and placenta and is produced by adipose tissue in men and postmenopausal women.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: estradiol

17β-estradiol is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 40.46
Molecular weight 272.18
XLogP 4.23
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES Oc1ccc2c(c1)CCC1C2CCC2(C1CCC2O)C
Isomeric SMILES Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
InChI InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1
InChI Key VOXZDWNPVJITMN-ZBRFXRBCSA-N
Natural/Endogenous Targets
Target
Estrogen receptor-α
Estrogen receptor-β
GPER
Pregnane X receptor
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
GPER Ligand is endogenous in the given species Hs Agonist Full agonist 8.2 – 8.5 pKi - 4-5
⤷ pKi 8.2 – 8.5 [4-5]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
KCa1.1 Hs Activator - 5.6 pEC50 - 6
⤷ pEC50 5.6 [6]
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Estrogen receptor-α Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist 9.8 pKi - 2
⤷ pKi 9.8 [2]
Estrogen receptor-β Ligand is endogenous in the given species Hs Agonist Agonist 9.3 pKi - 2
⤷ pKi 9.3 [2]
Pregnane X receptor Ligand is endogenous in the given species Hs Agonist Agonist - - - 1
⤷ [1]
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Proton-coupled Amino acid Transporter 1 Hs Inhibitor Inhibition 5.0 – 5.2 pIC50 - 3
⤷ pIC50 5.0 – 5.2 [3]
Targets where the ligand is described in the comment field
Target Comment
CYP19A1 Converts androstenedione and testosterone to estrone and 17β-estradiol, respectively.
Ligand mentioned in the following text fields
3C. 3-Ketosteroid receptors overview
Steroid hormone receptors overview
Maxi chloride channel comments