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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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
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1954, prior history unavailable))
Prodrug estradiol valerate
IUPAC Name Click here for help
(8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
International Nonproprietary Names Click here for help
INN number INN
406 estradiol
Synonyms Click here for help
estrogen | oestrodiol | oestrogen
Database Links Click here for help
Specialist databases
GPCRdb Ligand 17beta-estradiol
Other databases
CAS Registry No. 50-28-2 (source: DrugBank)
ChEBI CHEBI:16469
ChEMBL Ligand CHEMBL135
DrugBank Ligand DB00783
DrugCentral Ligand 1057
GtoPdb PubChem SID 135651381
PubChem CID 5757
RCSB PDB Ligand EST
Search Google for chemical match using the InChIKey VOXZDWNPVJITMN-ZBRFXRBCSA-N
Search Google for chemicals with the same backbone VOXZDWNPVJITMN
Search PubMed clinical trials estradiol
Search PubMed titles estradiol
Search PubMed titles/abstracts estradiol
SynPHARM 6509 (in complex with Estrogen receptor-α)
6522 (in complex with Estrogen receptor-β)
UniChem Compound Search for chemical match using the InChIKey VOXZDWNPVJITMN-ZBRFXRBCSA-N
UniChem Connectivity Search for chemical match using the InChIKey VOXZDWNPVJITMN-ZBRFXRBCSA-N
Wikipedia Estradiol

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Tocris
β-Estradiol (links to external site)
Cat. No. 2824