N-(3,4,5-trimethoxyphenyl)quinolin-4-amine

ID: ALA4586588

PubChem CID: 155566995

Max Phase: Preclinical

Molecular Formula: C18H18N2O3

Molecular Weight: 310.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(Nc2ccnc3ccccc23)cc(OC)c1OC

Standard InChI:  InChI=1S/C18H18N2O3/c1-21-16-10-12(11-17(22-2)18(16)23-3)20-15-8-9-19-14-7-5-4-6-13(14)15/h4-11H,1-3H3,(H,19,20)

Standard InChI Key:  YUFKUUNLQBRXJX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   33.3390  -11.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3379  -11.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6258  -10.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9183  -11.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9233  -11.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6319  -12.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6238   -9.8817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2047  -10.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2141  -12.3565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4997  -11.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2012   -9.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3346   -9.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0520  -12.3425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0544  -13.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3430  -13.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3450  -14.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0586  -14.8030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7660  -13.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7693  -14.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4779  -14.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1837  -14.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1764  -13.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4672  -13.1553    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA4586588

   ---

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: 310.35

Molecular Weight (Monoisotopic): 310.1317

AlogP: 4.00

#Rotatable Bonds: 5

Polar Surface Area: 52.61

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.30

CX LogP: 3.10

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.77

Np Likeness Score: -0.65

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