N1-[3-acetamido-5-(chloromethyl)phenyl]-N4-[3-(dimethylamino)propyl]terephthalamide

ID: ALA4759519

PubChem CID: 162658177

Max Phase: Preclinical

Molecular Formula: C22H27ClN4O3

Molecular Weight: 430.94

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(CCl)cc(NC(=O)c2ccc(C(=O)NCCCN(C)C)cc2)c1

Standard InChI:  InChI=1S/C22H27ClN4O3/c1-15(28)25-19-11-16(14-23)12-20(13-19)26-22(30)18-7-5-17(6-8-18)21(29)24-9-4-10-27(2)3/h5-8,11-13H,4,9-10,14H2,1-3H3,(H,24,29)(H,25,28)(H,26,30)

Standard InChI Key:  LIPZBAFVFYXITP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   21.0392  -11.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0381  -12.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7461  -12.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4558  -12.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4529  -11.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7443  -11.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7419  -10.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4484  -10.0722    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.3300  -12.9365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6226  -12.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9146  -12.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6233  -11.7101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1641  -12.9355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8712  -12.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5795  -12.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8699  -11.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5762  -13.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2837  -14.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9917  -13.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9878  -12.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2797  -12.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7006  -14.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7030  -14.9703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4071  -13.7424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1160  -14.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8226  -13.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5314  -14.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2380  -13.7342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9469  -14.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2356  -12.9170    0.0000 C   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
  6  7  1  0
  7  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 15  1  0
 19 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759519

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 430.94

Molecular Weight (Monoisotopic): 430.1772

AlogP: 3.32

#Rotatable Bonds: 9

Polar Surface Area: 90.54

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.78

CX Basic pKa: 9.30

CX LogP: 2.04

CX LogD: 0.15

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: -1.26

References

1. Khan GS,Pilkington LI,Barker D.  (2016)  Synthesis and biological activity of benzamide DNA minor groove binders.,  26  (3.0): [PMID:26739782] [10.1016/j.bmcl.2015.12.090]

Source

Source(1):

• Scientific Literature