rac-(3R,4S)-1-(2-chloro-6-fluorobenzyl)-N,N-dimethyl-4-(1-methyl-1H-indol-3-yl)pyrrolidin-3-amine

ID: ALA4095605

PubChem CID: 137655015

Max Phase: Preclinical

Molecular Formula: C22H25ClFN3

Molecular Weight: 385.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)[C@H]1CN(Cc2c(F)cccc2Cl)C[C@@H]1c1cn(C)c2ccccc12

Standard InChI:  InChI=1S/C22H25ClFN3/c1-25(2)22-14-27(13-18-19(23)8-6-9-20(18)24)12-17(22)16-11-26(3)21-10-5-4-7-15(16)21/h4-11,17,22H,12-14H2,1-3H3/t17-,22+/m1/s1

Standard InChI Key:  SGJDIPHHTWORQM-VGSWGCGISA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   23.0040   -6.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0029   -7.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7177   -8.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4342   -7.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4313   -6.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7158   -6.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1442   -6.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1411   -5.7023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8034   -5.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5456   -4.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7204   -4.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4686   -5.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0280   -3.7616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8488   -3.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6895   -3.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2305   -3.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4824   -2.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8131   -2.5024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4055   -3.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1503   -2.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3448   -2.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7939   -3.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0539   -4.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8588   -4.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8094   -1.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7134   -5.7083    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.1493   -8.1845    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 10 13  1  1
 13 14  1  0
 13 15  1  0
 16 17  2  0
 17 18  1  0
 18 20  1  0
 19 16  1  0
 11 16  1  6
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 18 25  1  0
  6 26  1  0
  4 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095605

   ---

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: 385.91

Molecular Weight (Monoisotopic): 385.1721

AlogP: 4.50

#Rotatable Bonds: 4

Polar Surface Area: 11.41

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.03

CX LogP: 4.56

CX LogD: 2.93

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: -1.20

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]

Source

Source(1):

• Scientific Literature