N-(3-(8-acetamidoquinolin-4-yl)phenyl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide

ID: ALA3087661

PubChem CID: 76331700

Max Phase: Preclinical

Molecular Formula: C26H21N3O4

Molecular Weight: 439.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cccc2c(-c3cccc(NC(=O)c4ccc5c(c4)OCCO5)c3)ccnc12

Standard InChI:  InChI=1S/C26H21N3O4/c1-16(30)28-22-7-3-6-21-20(10-11-27-25(21)22)17-4-2-5-19(14-17)29-26(31)18-8-9-23-24(15-18)33-13-12-32-23/h2-11,14-15H,12-13H2,1H3,(H,28,30)(H,29,31)

Standard InChI Key:  MTVIGRQJMNWLRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   15.6071  -24.8678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3224  -25.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0393  -24.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0365  -24.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6083  -24.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3195  -23.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3175  -22.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6049  -22.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8930  -22.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8986  -23.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7493  -23.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4642  -24.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1767  -23.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1733  -22.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4514  -22.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7419  -22.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8934  -24.0268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6065  -23.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3232  -24.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6030  -22.7856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1860  -24.0513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3224  -24.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0382  -25.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0297  -23.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7461  -24.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7516  -24.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4659  -25.2421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1793  -24.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1738  -24.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4550  -23.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4688  -23.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7562  -24.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4641  -22.8170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 10 21  1  0
 19 22  2  0
 22 23  1  0
 23 26  2  0
 25 24  2  0
 24 19  1  0
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 21 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3087661

   N-[3-(8-acetamidoquinolin-4-yl)phenyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide

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: 439.47

Molecular Weight (Monoisotopic): 439.1532

AlogP: 4.88

#Rotatable Bonds: 4

Polar Surface Area: 89.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.48

CX Basic pKa: 3.41

CX LogP: 3.62

CX LogD: 3.62

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.47

Np Likeness Score: -1.12

References

1. Koh EJ, El-Gamal MI, Oh CH, Lee SH, Sim T, Kim G, Choi HS, Hong JH, Lee SG, Yoo KH..  (2013)  New diarylamides and diarylureas possessing 8-amino(acetamido)quinoline scaffold: synthesis, antiproliferative activities against melanoma cell lines, kinase inhibition, and in silico studies.,  70  [PMID:24128410] [10.1016/j.ejmech.2013.06.060]

Source

Source(1):

• Scientific Literature