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

PRT3789   Click here for help

GtoPdb Ligand ID: 13837

Synonyms: compound 1 [WO2024076985A2] [2] | PRT-3789
Compound class: Synthetic organic
Comment: The structure presented here is claimed in patent WO2024076985A2 as a SMARCA2-selective degrader [2]. This same chemical structure was disclosed as Prelude Therapeutics' PRT3789 during the 'First Time disclosures' session at the ACS Spring 2025 meeting in San Diego. In patent US20240018158A1 Prelude Therapeutics claim degraders that interact with the SMARCA2 bromodomain, and E3 ubiquitin ligase to promote ubiquitin-mediated degradation. PRT3789 is one of these claims, although it difficult to ascertain which of the exemplar compounds is the exact stereoisomeric match to PRT3789. PRT3789 utilises a VHL-based E3 ligase binding moiety.
In therapeutic terms, reducing/inhibiting SMARCA2 is considered as a novel anti-tumour intervention [1], notably to exploit synthetic lethality in cancers that are SMARA4 deficient and that switch dependence to SMARCA2 for survival.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 14
Hydrogen bond donors 4
Rotatable bonds 15
Topological polar surface area 204.82
Molecular weight 891.09
XLogP 4.36
No. Lipinski's rules broken 3

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
Canonical SMILES CC(C)[C@H](C1=CC(=NO1)O[C@@H](C)CN2CC[C@H](C2)N3CCN4[C@@H](CNC5=NN=C(C=C54)C6=C(C=CC=C6)O)C3)C(=O)N7C[C@@H](C[C@H]7C(=O)N[C@@H](C)C8=CC=C(C=C8)C9=C(C)N=CS9)O
Isomeric SMILES CC(C)[C@H](C1=CC(=NO1)O[C@@H](C)CN2CC[C@H](C2)N3CCN4[C@@H](CNC5=C4C=C(C6=C(C=CC=C6)O)N=N5)C3)C(=O)N7C[C@@H](C[C@H]7C(=O)N[C@@H](C)C8=CC=C(C=C8)C9=C(C)N=CS9)O
InChI InChI=1S/C47H58N10O6S/c1-27(2)43(47(61)57-25-35(58)18-39(57)46(60)50-29(4)31-10-12-32(13-11-31)44-30(5)49-26-64-44)41-20-42(53-63-41)62-28(3)22-54-15-14-33(23-54)55-16-17-56-34(24-55)21-48-45-38(56)19-37(51-52-45)36-8-6-7-9-40(36)59/h6-13,19-20,26-29,33-35,39,43,58-59H,14-18,21-25H2,1-5H3,(H,48,52)(H,50,60)/t28-,29-,33+,34-,35+,39-,43+/m0/s1
InChI Key OSRJAZPHBNGCLU-CMMQWICPSA-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/)

For advanced searching click here to open chemical structure editor

Similar Ligands Click here for help
YX862
Click here for ligand page
KT-333
Click here for ligand page
Targets
signal transducer and activator of transcription 3
MS8709
Click here for ligand page
Targets
euchromatic histone lysine methyltransferase 1; euchromatic histone lysine methyltransferase 2
lirodegimod
Click here for ligand page
Targets
signal transducer and activator of transcription 3
SOS1 PROTAC 23
Click here for ligand page
WD6305
Click here for ligand page
Targets
methyltransferase 3, N6-adenosine-methyltransferase complex catalytic subunit
MS132
Click here for ligand page
Targets
WD repeat domain 5
SGI-1776-VHL-02
Click here for ligand page
PIM447-VHL-01
Click here for ligand page
SMD-3040
Click here for ligand page
Targets
SWI/SNF related BAF chromatin remodeling complex subunit ATPase 2; SWI/SNF related BAF chromatin remodeling complex subunit ATPase 4
compound 11 [PMID: 37449845]
Click here for ligand page
Targets
transglutaminase 2
CoV Mpro VHL PROTAC 9 [US11518759]
Click here for ligand page
Targets
CoV 3C-like (main) protease
A947
Click here for ligand page
Targets
SWI/SNF related BAF chromatin remodeling complex subunit ATPase 2; SWI/SNF related BAF chromatin remodeling complex subunit ATPase 4
NAMPT PROTAC B4
Click here for ligand page
MS15
Click here for ligand page
Targets
AKT serine/threonine kinase 1; AKT serine/threonine kinase 2; AKT serine/threonine kinase 3
C004019
Click here for ligand page
MS8815
Click here for ligand page
Targets
von Hippel-Lindau tumor suppressor
SOS1 PROTAC 9d
Click here for ligand page
Targets
SOS Ras/Rac guanine nucleotide exchange factor 1
XL01126
Click here for ligand page
Targets
leucine rich repeat kinase 2
AZ14117230
Click here for ligand page
Targets
embryonic ectoderm development
SIM1
Click here for ligand page
Targets
bromodomain containing 2
DT2216
Click here for ligand page
TBK1 PROTAC 3i
Click here for ligand page
Targets
TANK binding kinase 1
MZ1
Click here for ligand page
Targets
bromodomain containing 4
PROTAC 3
Click here for ligand page
MS39
Click here for ligand page
Targets
epidermal growth factor receptor
compound 3 [PMID: 31804822]
Click here for ligand page
Targets
mitogen-activated protein kinase kinase 1
ARD-266
Click here for ligand page
Targets
Androgen receptor
ERD-308
Click here for ligand page
Targets
Estrogen receptor-α
ARV-771
Click here for ligand page
Targets
bromodomain containing 2; bromodomain containing 3; bromodomain containing 4
MS432
Click here for ligand page
Targets
mitogen-activated protein kinase kinase 1; mitogen-activated protein kinase kinase 2
dTRIM24
Click here for ligand page
Targets
tripartite motif containing 24
SIAIS178
Click here for ligand page
Targets
ABL proto-oncogene 1, non-receptor tyrosine kinase
ARD-69
Click here for ligand page
Targets
Androgen receptor