7-Amino-6-chloro-benzo[1,2,5]thiadiazole-4-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

ID: ALA142687

PubChem CID: 15681450

Max Phase: Preclinical

Molecular Formula: C14H16ClN5OS

Molecular Weight: 337.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1c(Cl)cc(C(=O)NC2CN3CCC2CC3)c2nsnc12

Standard InChI:  InChI=1S/C14H16ClN5OS/c15-9-5-8(12-13(11(9)16)19-22-18-12)14(21)17-10-6-20-3-1-7(10)2-4-20/h5,7,10H,1-4,6,16H2,(H,17,21)

Standard InChI Key:  DNQOMGGYJRBLOX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    3.5417   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1125   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -3.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -2.9542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -2.8667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -2.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -1.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -4.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6875   -2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -5.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -6.2417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4000   -1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  7  2  0
  5  1  2  0
  6  1  1  0
  7  5  1  0
  8  2  2  0
  9  3  2  0
 10  9  1  0
 11  6  1  0
 12 11  1  0
 13 14  1  0
 14 12  1  0
 15  6  2  0
 16 12  1  0
 17  4  1  0
 18  7  1  0
 19 16  1  0
 20 16  1  0
 21 19  1  0
 22 20  1  0
  4  2  1  0
  8 10  1  0
 22 13  1  0
 21 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA142687

   4-amino-N-(1-azabicyclo[2.2.2]octan-3-yl)-5-chloro-2,1,3-benzothiadiazole-7-carboxamide

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: 337.84

Molecular Weight (Monoisotopic): 337.0764

AlogP: 1.75

#Rotatable Bonds: 2

Polar Surface Area: 84.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.91

CX LogP: 1.34

CX LogD: 0.72

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.82

Np Likeness Score: -1.09

References

1. Blum E, Buchheit K, Buescher H, Gamse R, Kloeppner E, Meigel H, Papageorgiou C, Waelchli R, Revesz L.  (1992)  Design and synthesis of novel ligands for the 5-HT3 and the 5-HT4 receptor,  2  (5): [10.1016/S0960-894X(00)80170-5]

Source

Source(1):

• Scientific Literature