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SOS1 PROTAC 23   Click here for help

GtoPdb Ligand ID: 13144

Synonyms: compound 23 [PMID: 38316747]
Compound class: Synthetic organic
Comment: This is a PROTAC degrader that targets the Son-of-sevenless homologue 1 (SOS1) protein [1] as a mechanism to disrupt RAS activation in cancers, particularly for potential to improve the antitumour response to KRASG12C inhibitors. PROTAC 23 engages SOS1 via a target-specific warhead (BI3406) that is linked to a ligand that engages the VHL E3 ubiquitin ligase.
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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Click here for structure editor
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 14
Hydrogen bond donors 5
Rotatable bonds 21
Topological polar surface area 217.63
Molecular weight 905.04
XLogP 2.67
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
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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 C[C@H](C1=CC(=CC(=C1)C(F)(F)F)N)NC2=C3C=C(C(=CC3=NC(=N2)C)OC)OCCCCC(=O)N[C@H](C(=O)N4C[C@@H](C[C@H]4C(=O)NCC5=CC=C(C=C5)C6=C(C)N=CS6)O)C(C)(C)C
Isomeric SMILES CC1=NC2=C(C(N[C@@H](C3=CC(N)=CC(C(F)(F)F)=C3)C)=N1)C=C(OCCCCC(N[C@H](C(N4C[C@@H](C[C@H]4C(NCC5=CC=C(C=C5)C6=C(N=CS6)C)=O)O)=O)C(C)(C)C)=O)C(OC)=C2
InChI InChI=1S/C46H55F3N8O6S/c1-25(30-16-31(46(47,48)49)18-32(50)17-30)53-42-34-20-38(37(62-7)21-35(34)54-27(3)55-42)63-15-9-8-10-39(59)56-41(45(4,5)6)44(61)57-23-33(58)19-36(57)43(60)51-22-28-11-13-29(14-12-28)40-26(2)52-24-64-40/h11-14,16-18,20-21,24-25,33,36,41,58H,8-10,15,19,22-23,50H2,1-7H3,(H,51,60)(H,56,59)(H,53,54,55)/t25-,33-,36+,41-/m1/s1
InChI Key PZZOZVWRQJUBBH-VXFROBSSSA-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/)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
(2S,4R)-1-((S)-2-(5-((4-(((R)-1-(3-Amino-5-(trifluoromethyl)phenyl)ethyl)amino)-7-methoxy-2-methylquinazolin-6-yl)oxy)pentanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
Synonyms Click here for help
compound 23 [PMID: 38316747]
Database Links Click here for help
GtoPdb PubChem SID 491299926
PubChem CID 171037440
Search Google for chemical match using the InChIKey PZZOZVWRQJUBBH-VXFROBSSSA-N
Search Google for chemicals with the same backbone PZZOZVWRQJUBBH
UniChem Compound Search for chemical match using the InChIKey PZZOZVWRQJUBBH-VXFROBSSSA-N
UniChem Connectivity Search for chemical match using the InChIKey PZZOZVWRQJUBBH-VXFROBSSSA-N