rac-(3R,4S)-1-(2-methoxybenzyl)-N,N-dimethyl-4-(1-methyl-1H-indol-3-yl)pyrrolidin-3-amine

ID: ALA4074159

Chembl Id: CHEMBL4074159

PubChem CID: 124037093

Max Phase: Preclinical

Molecular Formula: C23H29N3O

Molecular Weight: 363.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1CN1C[C@H](c2cn(C)c3ccccc23)[C@@H](N(C)C)C1

Standard InChI:  InChI=1S/C23H29N3O/c1-24(2)22-16-26(13-17-9-5-8-12-23(17)27-4)15-20(22)19-14-25(3)21-11-7-6-10-18(19)21/h5-12,14,20,22H,13,15-16H2,1-4H3/t20-,22+/m1/s1

Standard InChI Key:  CXQQECCQTKSQKN-IRLDBZIGSA-N

Alternative Forms

1. Parent:

   

   ALA4074159

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 363.51

Molecular Weight (Monoisotopic): 363.2311

AlogP: 3.72

#Rotatable Bonds: 5

Polar Surface Area: 20.64

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.29

CX LogP: 3.66

CX LogD: 1.77

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -0.65

References

1. Curtin ML, Pliushchev MA, Li HQ, Torrent M, Dietrich JD, Jakob CG, Zhu H, Zhao H, Wang Y, Ji Z, Clark RF, Sarris KA, Selvaraju S, Shaw B, Algire MA, He Y, Richardson PL, Sweis RF, Sun C, Chiang GG, Michaelides MR..  (2017)  SAR of amino pyrrolidines as potent and novel protein-protein interaction inhibitors of the PRC2 complex through EED binding.,  27  (7): [PMID:28254486] [10.1016/j.bmcl.2017.02.030]

2. Wang Y, Edalji RP, Panchal SC, Sun C, Djuric SW, Vasudevan A..  (2017)  Are We There Yet? Applying Thermodynamic and Kinetic Profiling on Embryonic Ectoderm Development (EED) Hit-to-Lead Program.,  60  (20): [PMID:28926243] [10.1021/acs.jmedchem.7b00576]

3. Martin MC,Zeng G,Yu J,Schiltz GE.  (2020)  Small Molecule Approaches for Targeting the Polycomb Repressive Complex 2 (PRC2) in Cancer.,  63  (24.0): [PMID:33283516] [10.1021/acs.jmedchem.0c01344]

4. Tomassi S, Romanelli A, Zwergel C, Valente S, Mai A..  (2021)  Polycomb Repressive Complex 2 Modulation through the Development of EZH2-EED Interaction Inhibitors and EED Binders.,  64  (16.0): [PMID:34351144] [10.1021/acs.jmedchem.1c00226]

5. Liu KL, Zhu K, Zhang H..  (2022)  An overview of the development of EED inhibitors to disable the PRC2 function.,  13  (1.0): [PMID:35224495] [10.1039/d1md00274k]

Source

Source(1):

• Scientific Literature