N-cyclooctyl-5-methoxy-1H-indole-2-carboxamide

ID: ALA5280212

Max Phase: Preclinical

Molecular Formula: C18H24N2O2

Molecular Weight: 300.40

Names and Identifiers

Canonical SMILES:  COc1ccc2[nH]c(C(=O)NC3CCCCCCC3)cc2c1

Standard InChI:  InChI=1S/C18H24N2O2/c1-22-15-9-10-16-13(11-15)12-17(20-16)18(21)19-14-7-5-3-2-4-6-8-14/h9-12,14,20H,2-8H2,1H3,(H,19,21)

Standard InChI Key:  VHRBBFBCKHSBRA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    2.0035    0.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232    0.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869    1.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8512    0.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1669    0.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8471   -0.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -0.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3215   -0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1827    0.2343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723   -0.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826   -1.1872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484   -0.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5343   -1.1449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3204   -0.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3204   -0.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5343    0.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328    0.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453   -0.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453   -0.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328   -1.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4555    0.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1669   -0.0619    0.0000 C   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 18  1  0
 22 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280212

   ---

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: 300.40

Molecular Weight (Monoisotopic): 300.1838

AlogP: 4.02

#Rotatable Bonds: 3

Polar Surface Area: 54.12

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.60

CX LogD: 3.60

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.90

Np Likeness Score: -0.85

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