ethyl 2-((4S)-6-(4-chlorophenyl)-1-methyl-4H-benzo[f][1,2,4]triazolo[4,3-a]azepin-4-yl)acetate

ID: ALA5276062

Max Phase: Preclinical

Molecular Formula: C22H20ClN3O2

Molecular Weight: 393.87

Names and Identifiers

Canonical SMILES:  CCOC(=O)C[C@H]1C=C(c2ccc(Cl)cc2)c2ccccc2-n2c(C)nnc21

Standard InChI:  InChI=1S/C22H20ClN3O2/c1-3-28-21(27)13-16-12-19(15-8-10-17(23)11-9-15)18-6-4-5-7-20(18)26-14(2)24-25-22(16)26/h4-12,16H,3,13H2,1-2H3/t16-/m1/s1

Standard InChI Key:  NRCOTKSVARGOIM-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

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   -1.8251    0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3175   -0.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4933   -0.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    0.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1502    1.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    1.6258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6138    0.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2127    0.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0232    1.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342    1.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7296   -0.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177   -1.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -2.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5539   -2.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654   -1.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5576   -0.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4257    1.8510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711    2.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0421    2.5813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3540    3.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8239    0.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0372   -0.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8335   -0.7648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543   -1.1344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4165   -0.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2127   -0.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661   -3.0251    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  5  4  1  0
  6  5  1  0
  7  6  1  0
  1  7  1  0
  2  8  1  0
  9  8  2  0
 10  9  1  0
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  1 11  1  0
 12  3  1  0
 13 12  2  0
 14 13  1  0
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 16 15  1  0
 12 17  1  0
 17 16  2  0
  6 18  2  0
  7 19  1  0
 19 20  2  0
 20 18  1  0
 19 21  1  0
  5 22  1  1
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 26 27  1  0
 15 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5276062

   ---

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: 393.87

Molecular Weight (Monoisotopic): 393.1244

AlogP: 4.71

#Rotatable Bonds: 4

Polar Surface Area: 57.01

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.99

CX LogP: 3.70

CX LogD: 3.70

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: -0.63

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