6-((4-(Dimethylamino)phenyl)(pyrimidin-2-ylamino)methyl)-benzo[d][1,3]dioxol-5-ol

ID: ALA4755608

PubChem CID: 162655232

Max Phase: Preclinical

Molecular Formula: C20H20N4O3

Molecular Weight: 364.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(C(Nc2ncccn2)c2cc3c(cc2O)OCO3)cc1

Standard InChI:  InChI=1S/C20H20N4O3/c1-24(2)14-6-4-13(5-7-14)19(23-20-21-8-3-9-22-20)15-10-17-18(11-16(15)25)27-12-26-17/h3-11,19,25H,12H2,1-2H3,(H,21,22,23)

Standard InChI Key:  JBKNXYFJSNUZBY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    9.5000   -9.3987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0195  -10.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5000  -10.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2888  -10.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2888   -9.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0005   -9.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7164   -9.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7164  -10.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0005  -10.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4322  -10.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4322   -9.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1439   -9.6517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8597   -9.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8597   -8.4142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5715   -8.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2873   -8.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2873   -9.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5715   -9.6517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4322   -8.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7164   -8.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7164   -7.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4322   -6.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1439   -7.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1439   -8.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4322   -5.9392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7164   -5.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1439   -5.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  5  6  2  0
  8 10  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 12 13  1  0
 11 12  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 25 26  1  0
 25 27  1  0
 22 25  1  0
 11 19  1  0
  7 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4755608

   ---

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: 364.41

Molecular Weight (Monoisotopic): 364.1535

AlogP: 3.18

#Rotatable Bonds: 5

Polar Surface Area: 79.74

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.42

CX Basic pKa: 4.83

CX LogP: 3.14

CX LogD: 3.13

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -0.70

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