5-Amino-6-chloro-quinoline-8-carboxylic acid (1-aza-bicyclo[3.3.1]non-4-yl)-amide

ID: ALA143871

PubChem CID: 44361170

Max Phase: Preclinical

Molecular Formula: C18H21ClN4O

Molecular Weight: 344.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1c(Cl)cc(C(=O)NC2CCN3CCCC2C3)c2ncccc12

Standard InChI:  InChI=1S/C18H21ClN4O/c19-14-9-13(17-12(16(14)20)4-1-6-21-17)18(24)22-15-5-8-23-7-2-3-11(15)10-23/h1,4,6,9,11,15H,2-3,5,7-8,10,20H2,(H,22,24)

Standard InChI Key:  ZXTPPBDZBKAHMV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  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
    4.2625   -3.7542    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   -4.1750    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
    2.1125   -5.0042    0.0000 C   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
    2.8250   -5.4167    0.0000 C   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
    5.8292   -1.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -2.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -2.9625    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
    5.3917   -2.1500    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
    1.4042   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -2.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4000   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  3  1  0
  5  1  1  0
  6  8  1  0
  7  2  1  0
  8  5  2  0
  9  7  1  0
 10 16  1  0
 11  9  1  0
 12  3  1  0
 13 11  1  0
 14  9  1  0
 15  2  2  0
 16 14  1  0
 17  6  1  0
 18  8  1  0
 19  4  1  0
 20 10  1  0
 21 11  1  0
 22 21  1  0
 23 12  2  0
 24 23  1  0
  4  6  2  0
 24 19  2  0
 13 10  1  0
 22 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA143871

   5-amino-N-(1-azabicyclo[3.3.1]nonan-4-yl)-6-chloroquinoline-8-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: 344.85

Molecular Weight (Monoisotopic): 344.1404

AlogP: 2.68

#Rotatable Bonds: 2

Polar Surface Area: 71.25

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.77

CX LogP: 1.46

CX LogD: 0.07

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.82

Np Likeness Score: -0.68

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