PHTPP-1304   Click here for help

GtoPdb Ligand ID: 12144

Compound class: Synthetic organic
Comment: PHTPP-1304 is a novel protein degrader [1-2]. It binds to the estrogen receptor β via the ERβ antagonist PHTPP domain, and simultaneously to the autophagy receptor p62, to target the ERβ . This class of degrader is called an AUTOphagy-TArgeting Chimera, or AUTOTAC. AUTOTACs can be designed to target proteins of interest to autophagic membranes where they undergo lysosomal degradation, in a proteasome-independent manner.
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 6
Hydrogen bond donors 2
Rotatable bonds 27
Topological polar surface area 117.83
Molecular weight 944.36
XLogP 9.98
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 O[C@@H](COc1ccc(c(c1)OCCCc1ccccc1)OCc1ccccc1)CNCCOCCOCCOc1ccc(cc1)c1c(nn2c1nc(cc2C(F)(F)F)C(F)(F)F)c1ccccc1
Isomeric SMILES O[C@H](CNCCOCCOCCOc1ccc(cc1)c1c2nc(cc(n2nc1c1ccccc1)C(F)(F)F)C(F)(F)F)COc1cc(OCCCc2ccccc2)c(OCc2ccccc2)cc1
InChI InChI=1S/C51H50F6N4O7/c52-50(53,54)45-32-46(51(55,56)57)61-49(59-45)47(48(60-61)39-16-8-3-9-17-39)38-18-20-41(21-19-38)65-30-29-64-28-27-63-26-24-58-33-40(62)35-67-42-22-23-43(68-34-37-13-6-2-7-14-37)44(31-42)66-25-10-15-36-11-4-1-5-12-36/h1-9,11-14,16-23,31-32,40,58,62H,10,15,24-30,33-35H2/t40-/m1/s1
InChI Key RFLBGKJLIDOOAA-RRHRGVEJSA-N
References
1. Ji CH, Kim HY, Lee MJ, Heo AJ, Park DY, Lim S, Shin S, Ganipisetti S, Yang WS, Jung CA et al.. (2022)
The AUTOTAC chemical biology platform for targeted protein degradation via the autophagy-lysosome system.
Nat Commun, 13 (1): 904. [PMID:35173167]
2. Kwon YT, Ji CH, Ganipisetti S, Kim HY, Mun SR, Jung CH, Jung EJ, Sung KW. (2021)
Novel autophagy-targeting chimera (autotac) compound, and composition for preventing, alleviating, or treating diseases through target protein degradation comprising same.
Patent number: EP3828164A1. Assignee: Protech Co Ltd. Priority date: 24/07/2018. Publication date: 02/06/2021.