6-((2,2-Difluorobenzo[d][1,3]dioxol-5-yl)(piperidin-1-yl)methyl)-benzofuran-7-ol

ID: ALA4776896

PubChem CID: 162643307

Max Phase: Preclinical

Molecular Formula: C21H19F2NO4

Molecular Weight: 387.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Oc1c(C(c2ccc3c(c2)OC(F)(F)O3)N2CCCCC2)ccc2ccoc12

Standard InChI:  InChI=1S/C21H19F2NO4/c22-21(23)27-16-7-5-14(12-17(16)28-21)18(24-9-2-1-3-10-24)15-6-4-13-8-11-26-20(13)19(15)25/h4-8,11-12,18,25H,1-3,9-10H2

Standard InChI Key:  YWTCGWLCGFLFTK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.3577  -12.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8780  -12.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1006  -12.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1001  -11.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3917  -13.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6824  -12.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6819  -11.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3907  -11.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3902  -10.5663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9767  -11.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2678  -11.7935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5585  -11.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8538  -11.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8543  -12.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5595  -13.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2684  -12.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1454   -8.1343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9558   -8.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2906   -8.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6804   -9.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9752   -8.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2663   -9.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2668  -10.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9762  -10.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6809  -10.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7328   -7.7947    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7886   -7.2474    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
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  5  9  2  0
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  9 10  1  0
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 18 22  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 22 23  2  0
 19 27  1  0
 19 28  1  0
 11 25  1  0
  8 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776896

   ---

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: 387.38

Molecular Weight (Monoisotopic): 387.1282

AlogP: 5.04

#Rotatable Bonds: 3

Polar Surface Area: 55.07

Molecular Species: ZWITTERION

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.09

CX Basic pKa: 9.21

CX LogP: 4.14

CX LogD: 4.14

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -0.26

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