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amcenestrant   Click here for help

GtoPdb Ligand ID: 10566

Synonyms: compound 43d [PMID: 31721572] | SAR-439859 | SAR439859
PDB Ligand
Compound class: Synthetic organic
Comment: Amcenestrant (SAR439859) is a selective estrogen receptor degrader (SERD) [1]. It was designed (by Sanofi) to have improved pharmacokinetic properties compared to the existing clinically used SERD, fulvestrant. An X-ray structure of SAR439859 in complex with the ERα ligand binding domain indicates that the ligand occupies the orthosteric estradiol binding cavity.
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 3
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 49.77
Molecular weight 553.16
XLogP 8.95
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES FCCCN1CCC(C1)Oc1ccc(cc1)C1=C(CCCc2c1ccc(c2)C(=O)O)c1ccc(cc1Cl)Cl
Isomeric SMILES FCCCN1CCC(C1)Oc1ccc(cc1)C1=C(CCCc2c1ccc(c2)C(=O)O)c1ccc(cc1Cl)Cl
InChI InChI=1S/C31H30Cl2FNO3/c32-23-8-12-27(29(33)18-23)28-4-1-3-21-17-22(31(36)37)7-11-26(21)30(28)20-5-9-24(10-6-20)38-25-13-16-35(19-25)15-2-14-34/h5-12,17-18,25H,1-4,13-16,19H2,(H,36,37)
InChI Key KISZAGQTIXIVAR-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. El-Ahmad Y, Tabart M, Halley F, Certal V, Thompson F, Filoche-Rommé B, Gruss-Leleu F, Muller C, Brollo M, Fabien L et al.. (2020)
Discovery of 6-(2,4-Dichlorophenyl)-5-[4-[(3S)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7H-benzo[7]annulene-2-carboxylic acid (SAR439859), a Potent and Selective Estrogen Receptor Degrader (SERD) for the Treatment of Estrogen-Receptor-Positive Breast Cancer.
J Med Chem, 63 (2): 512-528. DOI: 10.1021/acs.jmedchem.9b01293 [PMID:31721572]