4-Cyclopentyl-2-methyl-5-oxo-N-(o-tolyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxamide

ID: ALA4513816

PubChem CID: 155539179

Max Phase: Preclinical

Molecular Formula: C23H28N2O2

Molecular Weight: 364.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=C(C(=O)Nc2ccccc2C)C(C2CCCC2)C2=C(CCCC2=O)N1

Standard InChI:  InChI=1S/C23H28N2O2/c1-14-8-3-6-11-17(14)25-23(27)20-15(2)24-18-12-7-13-19(26)22(18)21(20)16-9-4-5-10-16/h3,6,8,11,16,21,24H,4-5,7,9-10,12-13H2,1-2H3,(H,25,27)

Standard InChI Key:  FTXMZBSYRAZADP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   11.9483   -3.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9483   -3.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6577   -4.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6577   -2.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3671   -3.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3637   -3.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0699   -4.2724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7840   -3.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7875   -3.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0768   -2.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6577   -1.8036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4894   -4.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4973   -2.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5016   -1.8175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2070   -3.0511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9210   -2.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6299   -3.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3434   -2.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3482   -1.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6335   -1.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9229   -1.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6245   -3.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0803   -1.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7427   -1.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4924   -0.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6752   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4206   -1.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  4 11  2  0
  8 12  1  0
  9 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 17 22  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 10 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513816

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 364.49

Molecular Weight (Monoisotopic): 364.2151

AlogP: 4.62

#Rotatable Bonds: 3

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.30

CX LogP: 3.73

CX LogD: 3.73

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -1.04

References

1. Ulven ER, Quon T, Sergeev E, Barki N, Brvar M, Hudson BD, Dutta P, Hansen AH, Bielefeldt LØ, Tobin AB, McKenzie CJ, Milligan G, Ulven T..  (2020)  Structure-Activity Relationship Studies of Tetrahydroquinolone Free Fatty Acid Receptor 3 Modulators.,  63  (7): [PMID:32141297] [10.1021/acs.jmedchem.9b02036]

Source

Source(1):

• Scientific Literature