4-(3,4,5-trimethoxyphenylamino)quinoline-7-carbonitrile

ID: ALA4575895

PubChem CID: 155563824

Max Phase: Preclinical

Molecular Formula: C19H17N3O3

Molecular Weight: 335.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(Nc2ccnc3cc(C#N)ccc23)cc(OC)c1OC

Standard InChI:  InChI=1S/C19H17N3O3/c1-23-17-9-13(10-18(24-2)19(17)25-3)22-15-6-7-21-16-8-12(11-20)4-5-14(15)16/h4-10H,1-3H3,(H,21,22)

Standard InChI Key:  BLWQIEISIMYCHD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.4142  -18.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4131  -18.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050  -17.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934  -18.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985  -18.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7112  -19.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7031  -16.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2799  -17.6254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2893  -19.2738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748  -18.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2764  -16.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4098  -16.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1272  -19.2598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1296  -20.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4181  -20.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4202  -21.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1338  -21.7203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8412  -20.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8445  -21.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5531  -21.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2588  -21.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2516  -20.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5424  -20.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9735  -21.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6882  -22.1000    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
  3  7  1  0
  4  8  1  0
  5  9  1  0
  9 10  1  0
  8 11  1  0
  7 12  1  0
  1 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 19  1  0
 18 14  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 18  2  0
 24 25  3  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4575895

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 335.36

Molecular Weight (Monoisotopic): 335.1270

AlogP: 3.88

#Rotatable Bonds: 5

Polar Surface Area: 76.40

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.01

CX LogP: 2.95

CX LogD: 2.95

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: -0.94

References

1. Asquith CRM, Berger BT, Wan J, Bennett JM, Capuzzi SJ, Crona DJ, Drewry DH, East MP, Elkins JM, Fedorov O, Godoi PH, Hunter DM, Knapp S, Müller S, Torrice CD, Wells CI, Earp HS, Willson TM, Zuercher WJ..  (2019)  SGC-GAK-1: A Chemical Probe for Cyclin G Associated Kinase (GAK).,  62  (5): [PMID:30768268] [10.1021/acs.jmedchem.8b01213]

2. Asquith CRM,Treiber DK,Zuercher WJ.  (2019)  Utilizing comprehensive and mini-kinome panels to optimize the selectivity of quinoline inhibitors for cyclin G associated kinase (GAK).,  29  (14.0): [PMID:31129055] [10.1016/j.bmcl.2019.05.025]

3. Saul S,Pu SY,Zuercher WJ,Einav S,Asquith CRM.  (2020)  Potent antiviral activity of novel multi-substituted 4-anilinoquin(az)olines.,  30  (16): [PMID:32631507] [10.1016/j.bmcl.2020.127284]

Source

Source(1):

• Scientific Literature