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

ID: ALA4537552

PubChem CID: 130439778

Max Phase: Preclinical

Molecular Formula: C23H19FN4O

Molecular Weight: 386.43

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H19FN4O/c1-5-15-10-11-19-17(12-15)20(16-8-6-7-9-18(16)24)26-14(2)22-21(23(29)27(3)4)25-13-28(19)22/h1,6-14H,2-4H3/t14-/m1/s1

Standard InChI Key:  LNPOWXXHIUMIKI-CQSZACIVSA-N

Molfile:  

 
     RDKit          2D

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   21.6530  -25.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3569  -26.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3551  -24.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0627  -25.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0596  -25.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7105  -26.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5135  -26.2369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8656  -25.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6980  -24.5773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5084  -24.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9202  -24.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3710  -23.4214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6173  -23.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5381  -27.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9533  -26.3209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2494  -26.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7291  -24.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1391  -24.7398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1364  -23.3285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7644  -27.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5918  -28.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1934  -28.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9703  -28.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1391  -27.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9163  -27.5090    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.6828  -25.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9536  -23.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7264  -22.6216    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
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  7  8  2  0
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  7 15  1  0
 16 17  3  0
  2 16  1  0
 12 18  1  0
 18 19  2  0
 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
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  9 27  1  1
 20 28  1  0
 20 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537552

   ---

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: 386.43

Molecular Weight (Monoisotopic): 386.1543

AlogP: 3.61

#Rotatable Bonds: 2

Polar Surface Area: 50.49

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.76

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: -1.11

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