ethyl 6-oxo-4,5,6,11-tetrahydro-1H-pyrrolo[2',3':5,6]azepino[4,3-b]indole-2-carboxylate

ID: ALA5270989

Max Phase: Preclinical

Molecular Formula: C17H15N3O3

Molecular Weight: 309.33

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2c([nH]1)-c1[nH]c3ccccc3c1C(=O)NC2

Standard InChI:  InChI=1S/C17H15N3O3/c1-2-23-17(22)12-7-9-8-18-16(21)13-10-5-3-4-6-11(10)19-15(13)14(9)20-12/h3-7,19-20H,2,8H2,1H3,(H,18,21)

Standard InChI Key:  VRDTYGBQEWABDM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -3.5716    0.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570    0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    0.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -0.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552   -0.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5716   -0.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604   -0.7238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3603    0.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754   -0.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0514   -0.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3439    1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3817    1.7256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    1.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3788   -0.7956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2455    0.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -0.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7237    1.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7638   -1.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609   -0.9735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -1.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7745   -0.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5716    0.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  4  7  1  0
  3  8  1  0
  8  9  2  0
  9  7  1  0
  9 10  1  0
 10 11  2  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
  8 14  1  0
 10 15  1  0
 11 16  1  0
 16 17  2  0
 17 15  1  0
 14 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5270989

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 309.33

Molecular Weight (Monoisotopic): 309.1113

AlogP: 2.58

#Rotatable Bonds: 2

Polar Surface Area: 86.98

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.42

CX Basic pKa: ┄

CX LogP: 1.74

CX LogD: 1.74

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: -0.01

References

1. Akunuri R, Vadakattu M, Bujji S, Veerareddy V, Madhavi YV, Nanduri S..  (2021)  Fused-azepinones: Emerging scaffolds of medicinal importance.,  220  [PMID:33901899] [10.1016/j.ejmech.2021.113445]

Source

Source(1):

• Scientific Literature