4-Amino-N-propyl-8-(pyrimidin-2-yl)cinnoline-3-carboxamide

ID: ALA1631468

Cas Number: 1261980-50-0

PubChem CID: 50915192

Max Phase: Preclinical

Molecular Formula: C16H16N6O

Molecular Weight: 308.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC(=O)c1nnc2c(-c3ncccn3)cccc2c1N

Standard InChI:  InChI=1S/C16H16N6O/c1-2-7-20-16(23)14-12(17)10-5-3-6-11(13(10)21-22-14)15-18-8-4-9-19-15/h3-6,8-9H,2,7H2,1H3,(H2,17,21)(H,20,23)

Standard InChI Key:  LHKDIYKHGIOMPL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.6861    1.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6849    1.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3998    0.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3980    2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1133    1.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1141    1.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8295    0.6367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5444    1.0515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5396    1.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8238    2.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026   -0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6873   -0.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4049   -1.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1207   -1.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1156   -0.5983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8195    3.1136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2517    2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9685    1.8901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2467    3.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6806    2.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3975    1.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1095    2.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 11 12  2  0
  5  6  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  6  7  1  0
 14 15  1  0
  1  2  2  0
 15 16  2  0
 16 11  1  0
  3 11  1  0
  7  8  2  0
 10 17  1  0
  5  4  2  0
  9 18  1  0
  8  9  1  0
 18 19  1  0
  4  1  1  0
 18 20  2  0
  9 10  2  0
 19 21  1  0
 10  5  1  0
 21 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1631468

   4-Amino-N-propyl-8-(pyrimidin-2-yl)cinnoline-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: 308.35

Molecular Weight (Monoisotopic): 308.1386

AlogP: 1.81

#Rotatable Bonds: 4

Polar Surface Area: 106.68

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.19

CX LogP: 1.53

CX LogD: 1.53

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: -1.31

References

1. Liu XF, Chang HF, Schmiesing RJ, Wesolowski SS, Knappenberger KS, Arriza JL, Chapdelaine MJ..  (2010)  Developing dual functional allosteric modulators of GABA(A) receptors.,  18  (23): [PMID:20980155] [10.1016/j.bmc.2010.09.058]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data