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

ID: ALA5282173

Max Phase: Preclinical

Molecular Formula: C17H23ClN2

Molecular Weight: 290.84

Names and Identifiers

Canonical SMILES:  Clc1ccc2[nH]c(CNC3CCCCCCC3)cc2c1

Standard InChI:  InChI=1S/C17H23ClN2/c18-14-8-9-17-13(10-14)11-16(20-17)12-19-15-6-4-2-1-3-5-7-15/h8-11,15,19-20H,1-7,12H2

Standard InChI Key:  CVMHKEQERLYETC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -3.8307    1.3140    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1168    0.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007    1.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847    0.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847    0.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007   -0.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1168    0.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8945   -0.1859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4061    0.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8945    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4188    0.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8312   -0.2285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6562   -0.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776    0.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7452    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135    0.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8307   -0.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -1.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7418   -1.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9759   -0.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  2  0
  4  3  1  0
  4  5  2  0
  5  6  1  0
  2  7  1  0
  7  6  2  0
  5  8  1  0
  8  9  1  0
  9 10  2  0
  4 10  1  0
  9 11  1  0
 11 12  1  0
 13 12  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
 13 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282173

   ---

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: 290.84

Molecular Weight (Monoisotopic): 290.1550

AlogP: 5.02

#Rotatable Bonds: 3

Polar Surface Area: 27.82

Molecular Species: BASE

HBA: 1

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.87

CX LogP: 4.84

CX LogD: 2.44

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.82

Np Likeness Score: -0.95

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