2-(3-chlorobenzo[b]thiophen-2-yl)-3-(4-nitrophenyl)quinazolin-4(3H)-one

ID: ALA4163780

PubChem CID: 145957305

Max Phase: Preclinical

Molecular Formula: C22H12ClN3O3S

Molecular Weight: 433.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1c2ccccc2nc(-c2sc3ccccc3c2Cl)n1-c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C22H12ClN3O3S/c23-19-16-6-2-4-8-18(16)30-20(19)21-24-17-7-3-1-5-15(17)22(27)25(21)13-9-11-14(12-10-13)26(28)29/h1-12H

Standard InChI Key:  HUNLGTRHASFQPN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   22.2609   -3.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2597   -4.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9678   -4.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9660   -3.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6746   -3.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6780   -4.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3903   -4.7330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1039   -4.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1005   -3.4945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3836   -3.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8127   -4.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3791   -2.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9010   -5.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5590   -4.3908    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.1075   -4.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7023   -5.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1109   -6.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9246   -6.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3280   -5.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9170   -4.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2965   -6.0875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.8059   -3.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5152   -3.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2211   -3.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2190   -2.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5051   -1.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8021   -2.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9286   -1.8522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9250   -1.0350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6381   -2.2576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 10 12  2  0
 11 13  2  0
 13 16  1  0
 15 14  1  0
 14 11  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 13 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  9 22  1  0
 28 29  2  0
 28 30  1  0
 25 28  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4163780

   ---

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: 433.88

Molecular Weight (Monoisotopic): 433.0288

AlogP: 5.83

#Rotatable Bonds: 3

Polar Surface Area: 78.03

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.06

CX LogD: 6.06

Aromatic Rings: 5

Heavy Atoms: 30

QED Weighted: 0.26

Np Likeness Score: -1.48

References

1. Keri RS, Chand K, Budagumpi S, Balappa Somappa S, Patil SA, Nagaraja BM..  (2017)  An overview of benzo[b]thiophene-based medicinal chemistry.,  138  [PMID:28759875] [10.1016/j.ejmech.2017.07.038]

Source

Source(1):

• Scientific Literature