N-cyclooctyl-6-hydroxy-1H-indole-2-carboxamide

ID: ALA5278413

Max Phase: Preclinical

Molecular Formula: C17H22N2O2

Molecular Weight: 286.38

Names and Identifiers

Canonical SMILES:  O=C(NC1CCCCCCC1)c1cc2ccc(O)cc2[nH]1

Standard InChI:  InChI=1S/C17H22N2O2/c20-14-9-8-12-10-16(19-15(12)11-14)17(21)18-13-6-4-2-1-3-5-7-13/h8-11,13,19-20H,1-7H2,(H,18,21)

Standard InChI Key:  DUYZIGZRKBIRDB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    1.6490    0.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687    0.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    1.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4969    0.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125    0.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927   -0.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7291   -0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9669   -0.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281    0.2343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4176   -0.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8280   -1.1873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -0.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8891   -1.1450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6754   -0.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6754   -0.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8891    0.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879    0.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004   -0.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004   -0.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879   -1.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8125   -1.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  1  8  1  0
  1  9  1  0
 10  9  1  0
 10 11  2  0
 12 10  1  0
 13 12  1  0
 14 13  1  0
 15 14  2  0
 12 16  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 20  1  0
 21 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278413

   ---

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: 286.38

Molecular Weight (Monoisotopic): 286.1681

AlogP: 3.72

#Rotatable Bonds: 2

Polar Surface Area: 65.12

Molecular Species: NEUTRAL

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.51

CX Basic pKa: ┄

CX LogP: 3.45

CX LogD: 3.45

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.79

Np Likeness Score: -0.44

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