MS8709   Click here for help

GtoPdb Ligand ID: 13288

Synonyms: Compound 10 [PMID: 38464025] [1] | MS-8709
Compound class: Synthetic organic
Comment: MS8709 is a first-in-class G9a/GLP PROTAC degrader whose structure was disclosed in preprint [1]. Note that in this context G9a and GLP are histone lysine methyltransferases encoded by EHMT2 and EHMT1 respectively. Excessive activation of the G9a/GLP axis promotes cancer progression, survival, and metastasis, making these targets for oncology drug development. Interaction with the target proteins is achieved by inclusion of the UNC0642 parent inhibitor, and this is linked to a von Hippel Lindau (VHL)-binding moiety to engage with the E3 ligase.
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 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.

✖
Hydrogen bond acceptors 18
Hydrogen bond donors 5
Rotatable bonds 36
Topological polar surface area 230.43
Molecular weight 1200.57
XLogP 7.52
No. Lipinski's rules broken 4
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.

✖
Canonical SMILES CC1=C(C2=CC=C(C=C2)CNC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCCNC(=O)CCCN4CCC(CC4)NC5=C6C=C(C(=CC6=NC(=N5)N7CCC(CC7)(F)F)OCCCN8CCCC8)OC)O)SC=N1
Isomeric SMILES FC1(CCN(CC1)C2=NC3=CC(=C(C=C3C(=N2)NC4CCN(CC4)CCCC(=O)NCCCCCCCCCCCC(=O)N[C@H](C(=O)N5[C@@H](C[C@H](C5)O)C(=O)NCC6=CC=C(C=C6)C7=C(N=CS7)C)C(C)(C)C)OC)OCCCN8CCCC8)F
InChI InChI=1S/C64H95F2N11O7S/c1-45-57(85-44-69-45)47-23-21-46(22-24-47)42-68-60(81)52-39-49(78)43-77(52)61(82)58(63(2,3)4)72-56(80)19-13-11-9-7-6-8-10-12-14-29-67-55(79)20-17-32-75-34-25-48(26-35-75)70-59-50-40-53(83-5)54(84-38-18-33-74-30-15-16-31-74)41-51(50)71-62(73-59)76-36-27-64(65,66)28-37-76/h21-24,40-41,44,48-49,52,58,78H,6-20,25-39,42-43H2,1-5H3,(H,67,79)(H,68,81)(H,72,80)(H,70,71,73)/t49-,52+,58-/m1/s1
InChI Key CLUWNSLFLMBFKA-RMCUFUCFSA-N
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-(12-(4-(4-((2-(4,4-difluoropiperidin-1-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazolin-4-yl)amino)piperidin-1-yl)butanamido)dodecanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
Synonyms Click here for help
Compound 10 [PMID: 38464025] [1] | MS-8709
Database Links Click here for help
GtoPdb PubChem SID 496703258
Search Google for chemical match using the InChIKey CLUWNSLFLMBFKA-RMCUFUCFSA-N
Search Google for chemicals with the same backbone CLUWNSLFLMBFKA
UniChem Compound Search for chemical match using the InChIKey CLUWNSLFLMBFKA-RMCUFUCFSA-N
UniChem Connectivity Search for chemical match using the InChIKey CLUWNSLFLMBFKA-RMCUFUCFSA-N