4-amino-8-(2-fluoro-6-methoxyphenyl)-N-propylcinnoline-3-carboxamide

ID: ALA1783282

Cas Number: 942437-37-8

PubChem CID: 23581869

Product Number: A412213, Order Now?

Max Phase: Phase

Molecular Formula: C19H19FN4O2

Molecular Weight: 354.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Azd7325 | AZD-7325|942437-37-8|4-amino-8-(2-fluoro-6-methoxyphenyl)-N-propylcinnoline-3-carboxamide|AZD7325|UNII-KNM216XOUH|KNM216XOUH|CHEMBL1783282|KYDURMHFWXCKMW-UHFFFAOYSA-N|GTPL7712|SCHEMBL1962584|AZD 7325 [WHO-DD]|AZD 7325|BCP29554|EX-A3618|BDBM50418481|MFCD21337369|AKOS037649295|AZD 7325; AZD7325|DB13994|SB17497|BS-17902|HY-111052|CS-0034076|NS00072939|D81581|Q27074785|4-amino-8-(2-fluoro-6-methoxy-phenyl)-N-propyl-cinnoline-3-carboxamide|4-Amino-8-(2-fluoro-6-methoxy-phenyl)-N-propylcinnoShow More⌵

Canonical SMILES:  CCCNC(=O)c1nnc2c(-c3c(F)cccc3OC)cccc2c1N

Standard InChI:  InChI=1S/C19H19FN4O2/c1-3-10-22-19(25)18-16(21)12-7-4-6-11(17(12)23-24-18)15-13(20)8-5-9-14(15)26-2/h4-9H,3,10H2,1-2H3,(H2,21,23)(H,22,25)

Standard InChI Key:  KYDURMHFWXCKMW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -4.5598  -12.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5609  -12.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8461  -13.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479  -11.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325  -12.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291  -12.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4099  -13.3657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168  -11.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213  -10.8746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8476  -14.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855  -12.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6912  -12.9507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9711  -11.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566  -12.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9713  -10.8770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4578  -11.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1724  -12.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8868  -11.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5639  -14.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5657  -15.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8515  -15.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1339  -15.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1356  -14.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2763  -14.1800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2721  -13.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4226  -14.1813    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 11 13  1  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 13 15  2  0
  5  8  1  0
 14 16  1  0
  6  7  1  0
 16 17  1  0
  7 12  2  0
 17 18  1  0
 11  8  2  0
 10 19  1  0
  5  4  2  0
 19 20  2  0
  8  9  1  0
 20 21  1  0
  4  1  1  0
 21 22  2  0
  3 10  1  0
 22 23  1  0
 23 10  2  0
 11 12  1  0
 19 24  1  0
  5  6  1  0
 24 25  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1783282

   AZD-7325

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 354.39

Molecular Weight (Monoisotopic): 354.1492

AlogP: 3.17

#Rotatable Bonds: 5

Polar Surface Area: 90.13

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.92

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.73

Np Likeness Score: -1.07

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]

2. Unpublished dataset, 

3. 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]

4. Hall A, Chanteux H, Ménochet K, Ledecq M, Schulze MED..  (2021)  Designing Out PXR Activity on Drug Discovery Projects: A Review of Structure-Based Methods, Empirical and Computational Approaches.,  64  (10.0): [PMID:34003642] [10.1021/acs.jmedchem.0c02245]

5. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - IncuCyte,  [10.6019/CHEMBL5303304]

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• EUbOPEN Chemogenomic Library