US9206167, 2

ID: ALA3982910

PubChem CID: 24963398

Max Phase: Preclinical

Molecular Formula: C23H23N3O2S

Molecular Weight: 405.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c2ccccc2cc1OCCN1CCN(c2cccc3sccc23)CC1

Standard InChI:  InChI=1S/C23H23N3O2S/c27-23-21(16-17-4-1-2-5-19(17)24-23)28-14-13-25-9-11-26(12-10-25)20-6-3-7-22-18(20)8-15-29-22/h1-8,15-16H,9-14H2,(H,24,27)

Standard InChI Key:  BOKAVZYMEBZBJT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078   -5.9988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6131   -7.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9147   -8.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2111   -7.4898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2060   -5.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043   -5.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5134   -8.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8088   -7.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1116   -8.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1191   -9.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8239  -10.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5198  -11.9472    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0288  -12.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4118  -10.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5211   -9.7357    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  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  9 10  1  0
 10 11  2  0
 11  2  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 15  1  0
 18 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 21  1  0
 29 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982910

   3-[2-[4-(1-benzothiophen-4-yl)piperazin-1-yl]ethoxy]-1H-quinolin-2-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 405.52

Molecular Weight (Monoisotopic): 405.1511

AlogP: 3.94

#Rotatable Bonds: 5

Polar Surface Area: 48.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.12

CX Basic pKa: 7.59

CX LogP: 4.10

CX LogD: 3.69

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -1.51

References

1.  (2015)  Piperazine-substituted benzothiophenes for treatment of mental disorders, 

Source

Source(1):

• BindingDB Database