2-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butyl)-2-(4-oxo-1,4,5,6-tetrahydroazepino[4,5-b]indol-3(2H)-yl)acetamide

ID: ALA3799039

PubChem CID: 127047902

Max Phase: Preclinical

Molecular Formula: C25H27N3O4

Molecular Weight: 433.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)NC(=O)C(c1ccc2c(c1)OCO2)N1CCc2c([nH]c3ccccc23)CC1=O

Standard InChI:  InChI=1S/C25H27N3O4/c1-25(2,3)27-24(30)23(15-8-9-20-21(12-15)32-14-31-20)28-11-10-17-16-6-4-5-7-18(16)26-19(17)13-22(28)29/h4-9,12,23,26H,10-11,13-14H2,1-3H3,(H,27,30)

Standard InChI Key:  RLSLDGQGGMQYGX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    6.4078    5.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0481    3.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5425    5.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8493    5.4565    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
    8.2091    6.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5670   -0.3274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7035    0.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1509    2.0073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6608    1.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2980    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8564    0.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7688    1.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325    2.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5908    2.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3616    7.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3437    7.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4962    8.0787    0.0000 C   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
  4 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 21 25  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 24 29  2  0
 25 26  2  0
  2 28  1  0
 20 30  1  0
 20 31  1  0
 20 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3799039

   ---

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: 433.51

Molecular Weight (Monoisotopic): 433.2002

AlogP: 3.48

#Rotatable Bonds: 3

Polar Surface Area: 83.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.82

CX LogD: 2.82

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.66

Np Likeness Score: -0.51

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