4-amino-N-cyclobutyl-8-(2,5-dimethoxyphenyl)-7-fluorocinnoline-3-carboxamide

ID: ALA1783273

PubChem CID: 54587228

Max Phase: Preclinical

Molecular Formula: C21H21FN4O3

Molecular Weight: 396.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(-c2c(F)ccc3c(N)c(C(=O)NC4CCC4)nnc23)c1

Standard InChI:  InChI=1S/C21H21FN4O3/c1-28-12-6-9-16(29-2)14(10-12)17-15(22)8-7-13-18(23)20(26-25-19(13)17)21(27)24-11-4-3-5-11/h6-11H,3-5H2,1-2H3,(H2,23,25)(H,24,27)

Standard InChI Key:  KADHNYOMTSABQA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   10.5486   -5.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5474   -6.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2622   -7.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2604   -5.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9758   -5.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9792   -6.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6984   -7.1740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6916   -5.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6870   -4.6829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2608   -7.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5444   -8.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5426   -9.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2569   -9.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9744   -9.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9727   -8.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6896   -9.6388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6911  -10.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8320   -7.9883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4186   -5.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4171   -6.7591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1155   -8.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8326   -7.1726    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.1319   -5.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8475   -5.9165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1296   -4.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5609   -5.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3554   -5.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5667   -4.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7692   -4.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
 15 10  1  0
  5  8  1  0
 14 16  1  0
  6  7  1  0
 16 17  1  0
  7 20  2  0
 11 18  1  0
 19 20  1  0
 19  8  2  0
  5  4  2  0
  8  9  1  0
 18 21  1  0
  4  1  1  0
  2 22  1  0
  3 10  1  0
 19 23  1  0
  5  6  1  0
 23 24  1  0
 10 11  2  0
 23 25  2  0
 24 26  1  0
 26 27  1  0
 11 12  1  0
  2  3  1  0
 12 13  2  0
 27 28  1  0
 28 29  1  0
 29 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1783273

   4-amino-N-cyclobutyl-8-(2,5-dimethoxyphenyl)-7-fluorocinnoline-3-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 396.42

Molecular Weight (Monoisotopic): 396.1598

AlogP: 3.32

#Rotatable Bonds: 5

Polar Surface Area: 99.36

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.36

CX LogP: 2.82

CX LogD: 2.82

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -0.88

References

1. Alhambra C, Becker C, Blake T, Chang AH, Damewood JR, Daniels T, Dembofsky BT, Gurley DA, Hall JE, Herzog KJ, Horchler CL, Ohnmacht CJ, Schmiesing RJ, Dudley A, Ribadeneira MD, Knappenberger KS, Maciag C, Stein MM, Chopra M, Liu XF, Christian EP, Arriza JL, Chapdelaine MJ..  (2011)  Development and SAR of functionally selective allosteric modulators of GABAA receptors.,  19  (9): [PMID:21498079] [10.1016/j.bmc.2011.03.035]

Source

Source(1):

• Scientific Literature