7-((3-fluorophenyl)(4-methylpyridin-2-ylamino)methyl)quinolin-8-ol

ID: ALA4755661

PubChem CID: 3163231

Max Phase: Preclinical

Molecular Formula: C22H18FN3O

Molecular Weight: 359.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccnc(NC(c2cccc(F)c2)c2ccc3cccnc3c2O)c1

Standard InChI:  InChI=1S/C22H18FN3O/c1-14-9-11-24-19(12-14)26-20(16-4-2-6-17(23)13-16)18-8-7-15-5-3-10-25-21(15)22(18)27/h2-13,20,27H,1H3,(H,24,26)

Standard InChI Key:  OTFQEKBHSZDRLM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    9.2280  -10.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0978   -9.1235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5177   -9.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5208   -7.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5188   -9.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8046   -8.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2262   -8.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0974   -7.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0941   -6.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8044   -7.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0802   -9.9349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3632  -10.3212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3452  -11.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0381  -11.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7540  -11.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7720  -10.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7911   -6.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5190   -6.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9369   -9.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9420   -9.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6579  -10.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3693   -9.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3602   -9.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6437   -8.7058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2221   -7.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4529  -11.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3837   -6.2702    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0
 10  4  2  0
  6 10  1  0
  9  8  2  0
 17  9  1  0
  7  5  1  0
  8 10  1  0
  5  6  1  0
 19  7  2  0
  5  3  2  0
  6  2  1  0
  4 18  1  0
  3  1  1  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  7 25  1  0
 15 26  1  0
  9 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4755661

   7-[(3-Fluorophenyl)[(4-methylpyridin-2-YL)amino]methyl]quinolin-8-OL

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: 359.40

Molecular Weight (Monoisotopic): 359.1434

AlogP: 4.98

#Rotatable Bonds: 4

Polar Surface Area: 58.04

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.55

CX Basic pKa: 7.28

CX LogP: 4.65

CX LogD: 4.56

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: -1.37

References

1. Shergalis A,Xue D,Gharbia FZ,Driks H,Shrestha B,Tanweer A,Cromer K,Ljungman M,Neamati N.  (2020)  Characterization of Aminobenzylphenols as Protein Disulfide Isomerase Inhibitors in Glioblastoma Cell Lines.,  63  (18): [PMID:32830969] [10.1021/acs.jmedchem.0c00728]

Source

Source(1):

• Scientific Literature