7-((4-hydroxy-3,5-dimethoxyphenyl)(5-methylpyridin-2-ylamino)methyl)quinolin-8-ol

ID: ALA4790355

PubChem CID: 162668822

Max Phase: Preclinical

Molecular Formula: C24H23N3O4

Molecular Weight: 417.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C(Nc2ccc(C)cn2)c2ccc3cccnc3c2O)cc(OC)c1O

Standard InChI:  InChI=1S/C24H23N3O4/c1-14-6-9-20(26-13-14)27-21(16-11-18(30-2)24(29)19(12-16)31-3)17-8-7-15-5-4-10-25-22(15)23(17)28/h4-13,21,28-29H,1-3H3,(H,26,27)

Standard InChI Key:  MITSWHDEOSTHCR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   12.5669  -13.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4254  -12.0510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8525  -12.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8556  -10.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8536  -12.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1394  -11.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5651  -11.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4280  -10.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4247   -9.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1392  -10.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7176  -11.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7222  -10.8281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0152  -10.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3067  -10.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3095  -11.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171  -12.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1259   -9.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8538   -9.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5983  -10.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2800  -12.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2850  -12.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0051  -13.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7206  -12.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7115  -12.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9909  -11.6238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5611  -10.8209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5564   -9.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5508   -8.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7174   -9.1806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0127   -9.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1177   -8.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  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
 20  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
 14 19  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  7 26  1  0
 27 28  1  0
 18 27  1  0
 29 30  1  0
  9 29  1  0
 17 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790355

   ---

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: 417.47

Molecular Weight (Monoisotopic): 417.1689

AlogP: 4.57

#Rotatable Bonds: 6

Polar Surface Area: 96.73

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.47

CX Basic pKa: 6.89

CX LogP: 3.91

CX LogD: 3.93

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: -0.75

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