4-((4-(3-Cyano-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinolin-4-yl)phenoxy)methyl)benzoic acid

ID: ALA4167562

PubChem CID: 145952958

Max Phase: Preclinical

Molecular Formula: C25H22N2O4

Molecular Weight: 414.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(C#N)C(c2ccc(OCc3ccc(C(=O)O)cc3)cc2)C2=C(CCCC2=O)N1

Standard InChI:  InChI=1S/C25H22N2O4/c1-15-20(13-26)23(24-21(27-15)3-2-4-22(24)28)17-9-11-19(12-10-17)31-14-16-5-7-18(8-6-16)25(29)30/h5-12,23,27H,2-4,14H2,1H3,(H,29,30)

Standard InChI Key:  PRZLSAOGJBOUGQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    1.8311  -11.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299  -12.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5380  -13.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2476  -12.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2448  -11.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5362  -11.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1219  -13.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4145  -12.6388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212  -13.8651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9510  -11.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6602  -11.8114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664  -11.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0740  -11.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7797  -11.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7771  -10.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0629  -10.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601  -10.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4827  -10.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8928   -9.3478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4735   -9.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1838   -8.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1864   -8.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4805   -7.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7702   -8.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7658   -8.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8927  -10.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1889  -10.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0573   -9.3511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6008  -10.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1909  -11.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1843  -12.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 27  1  0
 18 20  1  0
 26 19  1  0
 19 21  1  0
 20 21  2  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 26 27  2  0
 25 28  2  0
 26 29  1  0
 27 30  1  0
 30 31  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4167562

   ---

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: 414.46

Molecular Weight (Monoisotopic): 414.1580

AlogP: 4.46

#Rotatable Bonds: 5

Polar Surface Area: 99.42

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.06

CX Basic pKa: ┄

CX LogP: 3.21

CX LogD: 0.09

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.75

Np Likeness Score: -0.98

References

1. Xiong H, Han J, Wang J, Lu W, Wang C, Chen Y, Fulin Lian, Zhang N, Liu YC, Zhang C, Ding H, Jiang H, Lu W, Luo C, Zhou B..  (2018)  Discovery of 1,8-acridinedione derivatives as novel GCN5 inhibitors via high throughput screening.,  151  [PMID:29665527] [10.1016/j.ejmech.2018.02.005]

Source

Source(1):

• Scientific Literature