elacestrant   Click here for help

GtoPdb Ligand ID: 12339

Synonyms: ER-306323 | ER306323 | Orserdu® | RAD-1901 | RAD1901
Approved drug PDB Ligand
elacestrant is an approved drug (FDA & EMA (2023))
Compound class: Synthetic organic
Comment: Elacestrant is an orally bioactive, selective, non-steroidal dual estrogen receptor degrader (SERD)/selective estrogen receptor modulator (SERM; with antagonist action) [6]. It was developed primarily for antineoplastic potential (via its SERD action at high concentrations) [3]. It has also demonstrated potential to treat the vasomotor symptoms of the menopause with estrogen-like effects detected at low concentrations (SERM activity), but the pharmacology in this setting is very complex [4]. Elacestrant crosses the blood-brain barrier, so is predicted to provide efficacy against breast cancer metastases in the brain.
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 2
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 44.73
Molecular weight 458.29
XLogP 6.6
No. Lipinski's rules broken 1
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 CCNCCc1ccc(cc1)CN(c1cc(OC)ccc1[C@@H]1CCc2c(C1)ccc(c2)O)CC
Isomeric SMILES CCNCCc1ccc(cc1)CN(CC)c1c(ccc(c1)OC)[C@@H]1CCc2c(C1)ccc(c2)O
InChI InChI=1S/C30H38N2O2/c1-4-31-17-16-22-6-8-23(9-7-22)21-32(5-2)30-20-28(34-3)14-15-29(30)26-11-10-25-19-27(33)13-12-24(25)18-26/h6-9,12-15,19-20,26,31,33H,4-5,10-11,16-18,21H2,1-3H3/t26-/m1/s1
InChI Key SIFNOOUKXBRGGB-AREMUKBSSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA & EMA (2023))
IUPAC Name Click here for help
(6R)-6-[2-[ethyl-[[4-[2-(ethylamino)ethyl]phenyl]methyl]amino]-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-ol
International Nonproprietary Names Click here for help
INN number INN
10247 elacestrant
Synonyms Click here for help
ER-306323 | ER306323 | Orserdu® | RAD-1901 | RAD1901
Database Links Click here for help
BindingDB Ligand 349630
CAS Registry No. 722533-56-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL4297509
DrugBank Ligand DB06374
GtoPdb PubChem SID 479821130
PubChem CID 23642301
RCSB PDB Ligand I0V
Search Google for chemical match using the InChIKey SIFNOOUKXBRGGB-AREMUKBSSA-N
Search Google for chemicals with the same backbone SIFNOOUKXBRGGB
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UniChem Compound Search for chemical match using the InChIKey SIFNOOUKXBRGGB-AREMUKBSSA-N
UniChem Connectivity Search for chemical match using the InChIKey SIFNOOUKXBRGGB-AREMUKBSSA-N