5-(benzyloxy)-N-cyclooctyl-1H-indole-2-carboxamide

ID: ALA5285245

Max Phase: Preclinical

Molecular Formula: C24H28N2O2

Molecular Weight: 376.50

Names and Identifiers

Canonical SMILES:  O=C(NC1CCCCCCC1)c1cc2cc(OCc3ccccc3)ccc2[nH]1

Standard InChI:  InChI=1S/C24H28N2O2/c27-24(25-20-11-7-2-1-3-8-12-20)23-16-19-15-21(13-14-22(19)26-23)28-17-18-9-5-4-6-10-18/h4-6,9-10,13-16,20,26H,1-3,7-8,11-12,17H2,(H,25,27)

Standard InChI Key:  QTPJJRODZLOIRQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -3.4554    1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1620    2.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758    1.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758    0.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1692    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452    0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452   -0.4073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0362   -0.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113   -0.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113   -1.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238   -2.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0362   -1.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747   -1.8996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605   -1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747   -0.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4813   -1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -1.9418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918   -0.5203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -0.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0322    0.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7960    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5603    0.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758   -0.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5562   -1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7925   -1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0305   -1.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  1  6  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  2  0
 11 10  1  0
 11 12  2  0
 12 13  1  0
  9 14  1  0
 14 13  2  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 11 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 21 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 21 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285245

   ---

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: 376.50

Molecular Weight (Monoisotopic): 376.2151

AlogP: 5.59

#Rotatable Bonds: 5

Polar Surface Area: 54.12

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.32

CX LogD: 5.32

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -0.89

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