N-[3-acetamido-5-(hydroxymethyl)phenyl]-4-[[2-(diethylamino)acetyl]amino]benzamide

ID: ALA4740847

PubChem CID: 162646018

Max Phase: Preclinical

Molecular Formula: C22H28N4O4

Molecular Weight: 412.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN(CC)CC(=O)Nc1ccc(C(=O)Nc2cc(CO)cc(NC(C)=O)c2)cc1

Standard InChI:  InChI=1S/C22H28N4O4/c1-4-26(5-2)13-21(29)24-18-8-6-17(7-9-18)22(30)25-20-11-16(14-27)10-19(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:  SFCPDPQMXKOFJH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   19.7845   -3.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7834   -4.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4914   -4.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2011   -4.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1982   -3.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4896   -3.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4872   -2.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1937   -1.9787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0753   -4.8430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3680   -4.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6599   -4.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3686   -3.6166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9094   -4.8420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6165   -4.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3248   -4.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6152   -3.6151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3215   -5.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0290   -6.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7371   -5.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7331   -4.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0251   -4.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4459   -6.0596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1525   -5.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8614   -6.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1501   -4.8317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5679   -5.6448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2768   -6.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9833   -5.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5655   -4.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2720   -4.4170    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  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:

   

   ALA4740847

   ---

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: 12.86

CX Basic pKa: 7.67

CX LogP: 1.38

CX LogD: 0.92

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: -1.35

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