4-Methyl-1-(2-(4-propionylpiperazin-1-yl)ethyl)-5-((4-((6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-methyl)-1H-indole-2-carbonitrile

ID: ALA4210021

PubChem CID: 117636594

Max Phase: Preclinical

Molecular Formula: C33H39F3N8OS

Molecular Weight: 652.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)N1CCN(CCn2c(C#N)cc3c(C)c(CN4CCC(Nc5ncnc6sc(CC(F)(F)F)cc56)CC4)ccc32)CC1

Standard InChI:  InChI=1S/C33H39F3N8OS/c1-3-30(45)43-13-10-41(11-14-43)12-15-44-25(19-37)16-27-22(2)23(4-5-29(27)44)20-42-8-6-24(7-9-42)40-31-28-17-26(18-33(34,35)36)46-32(28)39-21-38-31/h4-5,16-17,21,24H,3,6-15,18,20H2,1-2H3,(H,38,39,40)

Standard InChI Key:  CUUAMNOCGMUEBO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 46 51  0  0  0  0  0  0  0  0999 V2000
   20.4036  -18.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4025  -19.2434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1105  -19.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1087  -18.0150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8132  -18.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8139  -19.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6022  -19.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0795  -18.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5944  -18.1629    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.8967  -18.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3011  -18.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1183  -18.1025    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.8884  -17.4020    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.7015  -17.3963    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.1116  -20.4696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8157  -20.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8153  -21.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5195  -22.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2291  -21.6951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2300  -20.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5213  -20.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9358  -22.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6445  -21.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3488  -22.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3479  -20.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6425  -20.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3448  -22.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0595  -20.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0575  -21.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8329  -21.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3143  -21.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8362  -20.6373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1312  -21.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9484  -21.2981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8311  -19.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5363  -19.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5312  -18.5888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2359  -18.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2327  -17.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5243  -16.9599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8173  -17.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8188  -18.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5223  -16.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2290  -15.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8136  -15.7359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9377  -16.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
  3 15  1  0
 15 16  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 24 29  1  0
 28 25  1  0
 25 26  2  0
 26 23  1  0
 24 27  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 28  1  0
 33 34  3  0
 31 33  1  0
 32 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 37 42  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 40 43  1  0
 43 44  1  0
 43 45  2  0
 44 46  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4210021

   4-Methyl-1-[2-(4-propanoylpiperazin-1-yl)ethyl]-5-[[4-[[6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl]amino]piperidin-1-yl]methyl]indole-2-carbonitrile

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: 652.79

Molecular Weight (Monoisotopic): 652.2920

AlogP: 5.56

#Rotatable Bonds: 9

Polar Surface Area: 93.32

Molecular Species: BASE

HBA: 9

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.76

CX LogP: 4.80

CX LogD: 3.30

Aromatic Rings: 4

Heavy Atoms: 46

QED Weighted: 0.25

Np Likeness Score: -1.72

References

1. Borkin D, Klossowski S, Pollock J, Miao H, Linhares BM, Kempinska K, Jin Z, Purohit T, Wen B, He M, Sun D, Cierpicki T, Grembecka J..  (2018)  Complexity of Blocking Bivalent Protein-Protein Interactions: Development of a Highly Potent Inhibitor of the Menin-Mixed-Lineage Leukemia Interaction.,  61  (11): [PMID:29738674] [10.1021/acs.jmedchem.8b00071]

Source

Source(1):

• Scientific Literature