4-amino-8-(2,5-dimethoxyphenyl)-7-fluoro-N-propylcinnoline-3-carboxamide

ID: ALA1783272

PubChem CID: 25133110

Max Phase: Preclinical

Molecular Formula: C20H21FN4O3

Molecular Weight: 384.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC(=O)c1nnc2c(-c3cc(OC)ccc3OC)c(F)ccc2c1N

Standard InChI:  InChI=1S/C20H21FN4O3/c1-4-9-23-20(26)19-17(22)12-6-7-14(21)16(18(12)24-25-19)13-10-11(27-2)5-8-15(13)28-3/h5-8,10H,4,9H2,1-3H3,(H2,22,24)(H,23,26)

Standard InChI Key:  PFZUQESQYBPRGB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -3.7389   -6.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401   -7.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253   -8.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0271   -6.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3117   -6.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -7.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5891   -8.1740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5959   -6.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005   -5.6829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0267   -8.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431   -9.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7449  -10.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306  -10.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131  -10.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3148   -9.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5979  -10.6388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5964  -11.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4555   -8.9883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8689   -6.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8704   -7.7591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1720   -9.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4549   -8.1726    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1556   -6.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5600   -6.9165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1579   -5.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2734   -6.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9890   -6.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7023   -6.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  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
 11 12  1  0
 26 27  1  0
  2  3  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1783272

   4-amino-8-(2,5-dimethoxyphenyl)-7-fluoro-N-propylcinnoline-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: 384.41

Molecular Weight (Monoisotopic): 384.1598

AlogP: 3.18

#Rotatable Bonds: 6

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: 2.79

CX LogD: 2.79

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -1.00

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