ARD-2585   Click here for help

GtoPdb Ligand ID: 11755

Synonyms: ARD2585 | compound 43 [PMID: 34473519]
PDB Ligand
Compound class: Synthetic organic
Comment: ARD-2585 is a highly potent and orally bioavailable PROTAC androgen receptor (AR) degrader molecule [1]. It was designed to reduce AR in metastatic castration-resistant prostate cancer (mCRPC), as an alternative mechanism to antagonising AR signaling with drugs such as enzalutamide and apalutamide. Structurally ARD-2585 is a bifunctional molecule that contains an AR antagonist ligand linked to a cereblon binding component, that targets the AR to the cereblon/cullin 4A E3 ligase complex for degradation. It shares structural similarities to bavdegalutamide, which was the first AR PROTAC to advance to clinical evaluation in humans.
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 13
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 149.4
Molecular weight 762.3
XLogP 5.26
No. Lipinski's rules broken 2
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 N#Cc1ccc(cc1Cl)N([C@@H]1CC[C@H](CC1)NC(=O)c1ccc(cc1)N1CCN(CC1)C1CN(C1)c1ccc2c(c1)C(=O)N(C2=O)C1CCC(=O)NC1=O)C
Isomeric SMILES Clc1c(C#N)ccc(N(C)[C@H]2CC[C@@H](CC2)NC(=O)c2ccc(N3CCN(C4CN(C4)c4cc5c(C(=O)N(C6C(=O)NC(=O)CC6)C5=O)cc4)CC3)cc2)c1
InChI InChI=1S/C41H43ClN8O5/c1-46(30-9-4-26(22-43)35(42)21-30)28-10-5-27(6-11-28)44-38(52)25-2-7-29(8-3-25)47-16-18-48(19-17-47)32-23-49(24-32)31-12-13-33-34(20-31)41(55)50(40(33)54)36-14-15-37(51)45-39(36)53/h2-4,7-9,12-13,20-21,27-28,32,36H,5-6,10-11,14-19,23-24H2,1H3,(H,44,52)(H,45,51,53)/t27-,28-,36?
InChI Key LUCHABJUYSYJAT-RVWRWSNSSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
Synonyms Click here for help
ARD2585 | compound 43 [PMID: 34473519]
Database Links Click here for help
GtoPdb PubChem SID 458923790
PubChem CID 162366967
RCSB PDB Ligand 0QQ
Search Google for chemical match using the InChIKey LUCHABJUYSYJAT-RVWRWSNSSA-N
Search Google for chemicals with the same backbone LUCHABJUYSYJAT
UniChem Compound Search for chemical match using the InChIKey LUCHABJUYSYJAT-RVWRWSNSSA-N
UniChem Connectivity Search for chemical match using the InChIKey LUCHABJUYSYJAT-RVWRWSNSSA-N