2-(4-((4-(2,3-Dichlorophenoxy)benzyl)oxy)piperidin-1-yl)-N-methylethan-1-amine

ID: ALA3984626

PubChem CID: 134156697

Max Phase: Preclinical

Molecular Formula: C21H26Cl2N2O2

Molecular Weight: 409.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCCN1CCC(OCc2ccc(Oc3cccc(Cl)c3Cl)cc2)CC1

Standard InChI:  InChI=1S/C21H26Cl2N2O2/c1-24-11-14-25-12-9-17(10-13-25)26-15-16-5-7-18(8-6-16)27-20-4-2-3-19(22)21(20)23/h2-8,17,24H,9-15H2,1H3

Standard InChI Key:  NHEFIVVNRQJHSA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    6.6892   -9.1005    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4015   -9.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1138   -9.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1138   -8.2755    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8302   -9.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5425   -9.1005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2548   -9.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9670   -9.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6793   -9.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6793  -10.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3957  -10.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1080  -10.3360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8203  -10.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5367  -10.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2490  -10.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2490  -11.5715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9613  -11.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6736  -11.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6736  -10.7464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3900  -10.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5367  -11.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8203  -11.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9670  -10.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2548  -10.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8302  -10.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1138  -10.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4015  -10.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 13 22  1  0
 10 23  1  0
 23 24  2  0
  7 24  1  0
  5 25  2  0
 25 26  1  0
 26 27  2  0
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3984626

   ---

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: 409.36

Molecular Weight (Monoisotopic): 408.1371

AlogP: 4.99

#Rotatable Bonds: 8

Polar Surface Area: 33.73

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.94

CX LogP: 4.22

CX LogD: 1.73

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -0.92

References

1. Shen Y, Szewczyk MM, Eram MS, Smil D, Kaniskan HÜ, de Freitas RF, Senisterra G, Li F, Schapira M, Brown PJ, Arrowsmith CH, Barsyte-Lovejoy D, Liu J, Vedadi M, Jin J..  (2016)  Discovery of a Potent, Selective, and Cell-Active Dual Inhibitor of Protein Arginine Methyltransferase 4 and Protein Arginine Methyltransferase 6.,  59  (19): [PMID:27584694] [10.1021/acs.jmedchem.6b01033]

Source

Source(1):

• Scientific Literature