N-((5-nitro-1H-indol-2-yl)methyl)cyclooctanamine

ID: ALA5287632

Max Phase: Preclinical

Molecular Formula: C17H23N3O2

Molecular Weight: 301.39

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc2[nH]c(CNC3CCCCCCC3)cc2c1

Standard InChI:  InChI=1S/C17H23N3O2/c21-20(22)16-8-9-17-13(11-16)10-15(19-17)12-18-14-6-4-2-1-3-5-7-14/h8-11,14,18-19H,1-7,12H2

Standard InChI Key:  PGSGHIXXYWBNCJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -3.4732    0.9015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4732    1.7265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1883    0.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7593    0.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    0.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271    0.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432   -0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7593   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369   -0.5983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0485    0.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7764    0.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1888   -0.6409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0138   -0.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3352    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028    0.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8712    0.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1883   -0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8671   -1.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0995   -1.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3335   -1.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  1  4  1  0
  5  4  2  0
  6  5  1  0
  6  7  2  0
  7  8  1  0
  4  9  1  0
  9  8  2  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
  6 12  1  0
 11 13  1  0
 13 14  1  0
 15 14  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 15 22  1  0
M  CHG  2   1   1   3  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5287632

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 301.39

Molecular Weight (Monoisotopic): 301.1790

AlogP: 4.28

#Rotatable Bonds: 4

Polar Surface Area: 70.96

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.81

CX LogP: 4.18

CX LogD: 1.83

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.65

Np Likeness Score: -1.10

References

1. Tan YJ, Li M, Gunawan GA, Nyantakyi SA, Dick T, Go ML, Lam Y..  (2021)  Amide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility.,  12  (5.0): [PMID:34055215] [10.1021/acsmedchemlett.0c00588]

Source

Source(1):

• Scientific Literature