3-((4-bromophenyl)(1-tert-butyl-1H-tetrazol-5-yl)methyl)-2,3,5,6-tetrahydroazepino[4,5-b]indol-4(1H)-one

ID: ALA3799674

PubChem CID: 72696315

Max Phase: Preclinical

Molecular Formula: C24H25BrN6O

Molecular Weight: 493.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)n1nnnc1C(c1ccc(Br)cc1)N1CCc2c([nH]c3ccccc23)CC1=O

Standard InChI:  InChI=1S/C24H25BrN6O/c1-24(2,3)31-23(27-28-29-31)22(15-8-10-16(25)11-9-15)30-13-12-18-17-6-4-5-7-19(17)26-20(18)14-21(30)32/h4-11,22,26H,12-14H2,1-3H3

Standard InChI Key:  WOQBVIPHRNHEPD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -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
   -1.2488    4.0196    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
   -0.7025    1.4634    0.0000 C   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
    2.0878    4.1757    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
    3.5903    4.2733    0.0000 C   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
    4.6050    3.1610    0.0000 N   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
    6.0486    3.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4076    5.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7926    5.5784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6868    7.0747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2311    7.4364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4372    6.1637    0.0000 N   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 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.9436    6.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635    7.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4271    4.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473    5.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  9  5  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 10 12  1  0
 11 13  1  0
 12 14  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 16 22  1  0
 25 28  1  0
 21 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3799674

   3-[(4-Bromophenyl)-(1-tert-butyltetrazol-5-yl)methyl]-1,2,5,6-tetrahydroazepino[4,5-b]indol-4-one

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: 493.41

Molecular Weight (Monoisotopic): 492.1273

AlogP: 4.39

#Rotatable Bonds: 3

Polar Surface Area: 79.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.25

CX LogD: 4.25

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -1.22

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