1-(cyclopropylmethyl)-5-fluoro-4-methyl-N-(5-(1-methyl-1H-imidazol-4-yl)pyridin-2-yl)-1H-benzo[d]imidazol-6-amine

ID: ALA4581355

Cas Number: 1802661-73-9

PubChem CID: 118278442

Product Number: O412143, Order Now?

Max Phase: Preclinical

Molecular Formula: C21H21FN6

Molecular Weight: 376.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(F)c(Nc2ccc(-c3cn(C)cn3)cn2)cc2c1ncn2CC1CC1

Standard InChI:  InChI=1S/C21H21FN6/c1-13-20(22)16(7-18-21(13)25-12-28(18)9-14-3-4-14)26-19-6-5-15(8-23-19)17-10-27(2)11-24-17/h5-8,10-12,14H,3-4,9H2,1-2H3,(H,23,26)

Standard InChI Key:  INGJMHPGMVUEKY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   10.6952  -24.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4033  -24.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4015  -22.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9872  -24.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2798  -24.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2850  -23.3821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5784  -22.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8694  -23.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8714  -24.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1101  -23.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1149  -24.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8949  -24.4442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3723  -23.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8872  -23.1197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9886  -22.9723    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.3990  -22.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1609  -22.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750  -22.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2755  -21.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8673  -22.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4145  -23.3065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9427  -21.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9969  -26.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4103  -25.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 19  1  0
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  9 21  1  0
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 28 27  1  0
 18 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4581355

   ONO-8590580

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: 376.44

Molecular Weight (Monoisotopic): 376.1812

AlogP: 4.43

#Rotatable Bonds: 5

Polar Surface Area: 60.56

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.85

CX Basic pKa: 6.42

CX LogP: 3.87

CX LogD: 3.84

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -1.30

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]

2. Lewis A,Beresford A,Chambers MS,Clark G,Hartley DC,Hirst KL,Higashino M,Kawahadara S,Nakanishi M,Saito T,Imagawa A,Habashita H,Maidment S,Macleod AM,Owens AP,Rae A,Rouse C,Wishart G.  (2020)  Discovery of ONO-8590580: A novel, potent and selective GABA α negative allosteric modulator for the treatment of cognitive disorders.,  30  (22): [PMID:32898695] [10.1016/j.bmcl.2020.127536]

Source

Source(1):

• Scientific Literature