GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

ARD-1676   Click here for help

GtoPdb Ligand ID: 13248

Synonyms: ARD1676 | compound 39 [PMID: 37683104]
Compound class: Synthetic organic
Comment: ARD-1676 is a potent orally bioactive androgen receptor (AR) PROTAC [1]. The PROTAC includes TX-16 to engage the cereblon E3 ubiquitin lagase. ARD-1676 was designed as a potential prostate cancer therapy.

ARD-1676 is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 12
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 137.37
Molecular weight 788.33
XLogP 2.5
No. Lipinski's rules broken 2

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
Click here for help

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/)

✖
Canonical SMILES C[C@H]1CC2(CCN(CC2)C3=CC=C(C=C3)C(=O)N4CCC(CC4)CN5CC6=C(C=C7C(=C6)C(=O)N(C8CCC(=O)NC8=O)C7=O)C5)CN1C9=CC=C(C#N)C(=C9)Cl
Isomeric SMILES ClC1=C(C#N)C=CC(N2[C@@H](C)CC3(CCN(C4=CC=C(C(N5CCC(CN6CC7=CC8=C(C(N(C9C(NC(CC9)=O)=O)C8=O)=O)C=C7C6)CC5)=O)C=C4)CC3)C2)=C1
InChI InChI=1S/C44H46ClN7O5/c1-27-21-44(26-51(27)34-7-4-30(22-46)37(45)20-34)12-16-49(17-13-44)33-5-2-29(3-6-33)41(55)50-14-10-28(11-15-50)23-48-24-31-18-35-36(19-32(31)25-48)43(57)52(42(35)56)38-8-9-39(53)47-40(38)54/h2-7,18-20,27-28,38H,8-17,21,23-26H2,1H3,(H,47,53,54)/t27-,38?/m0/s1
InChI Key GAXWAKXJBZHVQF-ZVENJKCTSA-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. Xiang W, Zhao L, Han X, Xu T, Kregel S, Wang M, Miao B, Qin C, Wang M, McEachern D et al.. (2023)
Discovery of ARD-1676 as a Highly Potent and Orally Efficacious AR PROTAC Degrader with a Broad Activity against AR Mutants for the Treatment of AR + Human Prostate Cancer.
J Med Chem, 66 (18): 13280-13303. [PMID:37683104]