2-(4-chlorophenyl)-N-(2,6-dimethylphenyl)-2-(4-oxo-1,4,5,6-tetrahydroazepino[4,5-b]indol-3(2H)-yl)acetamide

ID: ALA3800049

PubChem CID: 127046453

Max Phase: Preclinical

Molecular Formula: C28H26ClN3O2

Molecular Weight: 471.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C)c1NC(=O)C(c1ccc(Cl)cc1)N1CCc2c([nH]c3ccccc23)CC1=O

Standard InChI:  InChI=1S/C28H26ClN3O2/c1-17-6-5-7-18(2)26(17)31-28(34)27(19-10-12-20(29)13-11-19)32-15-14-22-21-8-3-4-9-23(21)30-24(22)16-25(32)33/h3-13,27,30H,14-16H2,1-2H3,(H,31,34)

Standard InChI Key:  JGULJSGDGBKDOE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    6.4076    5.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0486    3.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5602    5.3703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3256    6.0768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5073    0.6244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6976    1.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488    2.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342    2.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2488    4.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7122    3.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001    2.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1854    1.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025    1.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6050    3.1610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3903    1.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0830    0.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0878    4.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903    4.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3830    1.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6846    7.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6048    8.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9665   10.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4080   10.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4879    9.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1262    7.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9901    7.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4515    8.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1305    2.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7739    1.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8573    0.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2975    0.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6542    1.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5707    2.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1642   -0.3656    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  5 13  1  0
  8 13  2  0
 14 15  1  0
 15 16  1  0
 17 18  1  0
 14 18  1  0
  6 16  1  0
  7 17  1  0
 15 19  2  0
  2 14  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 25 26  1  0
 21 27  1  0
  4 20  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 28 33  2  0
 31 34  1  0
  2 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3800049

   ---

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: 471.99

Molecular Weight (Monoisotopic): 471.1714

AlogP: 5.75

#Rotatable Bonds: 4

Polar Surface Area: 65.20

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.40

CX Basic pKa: ┄

CX LogP: 5.79

CX LogD: 5.79

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.40

Np Likeness Score: -0.97

References

1. Rentería-Gómez A, Islas-Jácome A, Díaz-Cervantes E, Villaseñor-Granados T, Robles J, Gámez-Montaño R..  (2016)  Synthesis of azepino[4,5-b]indol-4-ones via MCR/free radical cyclization and in vitro-in silico studies as 5-Ht₆R ligands.,  26  (9): [PMID:26996373] [10.1016/j.bmcl.2016.03.036]

Source

Source(1):

• Scientific Literature