(4R)-N-cyclopropyl-8-ethynyl-6-(2-fluorophenyl)-4-methyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxamide

ID: ALA4553352

PubChem CID: 130439889

Max Phase: Preclinical

Molecular Formula: C24H19FN4O

Molecular Weight: 398.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C#Cc1ccc2c(c1)C(c1ccccc1F)=N[C@H](C)c1c(C(=O)NC3CC3)ncn1-2

Standard InChI:  InChI=1S/C24H19FN4O/c1-3-15-8-11-20-18(12-15)21(17-6-4-5-7-19(17)25)27-14(2)23-22(26-13-29(20)23)24(30)28-16-9-10-16/h1,4-8,11-14,16H,9-10H2,2H3,(H,28,30)/t14-/m1/s1

Standard InChI Key:  YLZWVRAOJGXWTI-CQSZACIVSA-N

Molfile:  

 
     RDKit          2D

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   28.9305  -25.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9293  -26.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6332  -26.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6314  -25.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3390  -26.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3359  -25.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9868  -26.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7898  -26.7900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1420  -26.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9743  -25.1304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7847  -25.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1965  -24.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6473  -23.9744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8936  -24.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8144  -27.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2296  -26.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5257  -27.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0054  -24.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4154  -25.2928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4127  -23.8815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0407  -28.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8682  -28.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4697  -29.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2466  -29.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4154  -28.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1926  -28.0621    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.9591  -26.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2299  -23.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9379  -24.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9363  -23.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  6  4  2  0
  4  1  1  0
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  6 10  1  0
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  7  8  2  0
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  8  9  1  0
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 11 12  2  0
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  7 15  1  0
 16 17  3  0
  2 16  1  0
 12 18  1  0
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 18 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 15  1  0
 25 26  1  0
  9 27  1  1
 20 28  1  0
 29 28  1  0
 30 29  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553352

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 398.44

Molecular Weight (Monoisotopic): 398.1543

AlogP: 3.80

#Rotatable Bonds: 3

Polar Surface Area: 59.28

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.75

CX LogP: 3.74

CX LogD: 3.74

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.68

Np Likeness Score: -1.12

References

1. Maramai S, Benchekroun M, Ward SE, Atack JR..  (2020)  Subtype Selective γ-Aminobutyric Acid Type A Receptor (GABA_AR) Modulators Acting at the Benzodiazepine Binding Site: An Update.,  63  (7): [PMID:31738537] [10.1021/acs.jmedchem.9b01312]

Source

Source(1):

• Scientific Literature