N-[3-acetamido-5-(hydroxymethyl)phenyl]-3-[[2-(diethylamino)acetyl]amino]benzamide

ID: ALA4748123

PubChem CID: 162649177

Max Phase: Preclinical

Molecular Formula: C22H28N4O4

Molecular Weight: 412.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN(CC)CC(=O)Nc1cccc(C(=O)Nc2cc(CO)cc(NC(C)=O)c2)c1

Standard InChI:  InChI=1S/C22H28N4O4/c1-4-26(5-2)13-21(29)24-18-8-6-7-17(11-18)22(30)25-20-10-16(14-27)9-19(12-20)23-15(3)28/h6-12,27H,4-5,13-14H2,1-3H3,(H,23,28)(H,24,29)(H,25,30)

Standard InChI Key:  HPEJGUYMOOPUKX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    4.5716   -3.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704   -4.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2785   -4.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9881   -4.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853   -3.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2767   -2.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2742   -2.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9807   -1.7599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8624   -4.6242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550   -4.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4470   -4.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1556   -3.3979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6965   -4.6232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4035   -4.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1119   -4.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4022   -3.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1085   -5.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8160   -5.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5241   -5.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5202   -4.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8121   -4.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2258   -4.2007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9356   -4.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6412   -4.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9397   -5.4228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3510   -4.5984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0566   -4.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7664   -4.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3551   -5.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0649   -5.8206    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
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4748123

   ---

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: 412.49

Molecular Weight (Monoisotopic): 412.2111

AlogP: 2.67

#Rotatable Bonds: 9

Polar Surface Area: 110.77

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.08

CX Basic pKa: 7.68

CX LogP: 1.38

CX LogD: 0.91

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: -1.47

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