N-(2,5-Dichlorophenyl)-2-methyl-5-oxo-4-(piperidin-4-ylmethyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxamide

ID: ALA4538973

PubChem CID: 155544536

Max Phase: Preclinical

Molecular Formula: C23H27Cl2N3O2

Molecular Weight: 448.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=C(C(=O)Nc2cc(Cl)ccc2Cl)C(CC2CCNCC2)C2=C(CCCC2=O)N1

Standard InChI:  InChI=1S/C23H27Cl2N3O2/c1-13-21(23(30)28-19-12-15(24)5-6-17(19)25)16(11-14-7-9-26-10-8-14)22-18(27-13)3-2-4-20(22)29/h5-6,12,14,16,26-27H,2-4,7-11H2,1H3,(H,28,30)

Standard InChI Key:  CJEJZAPXRVGVEQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   21.5606  -14.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5606  -15.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2700  -15.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2700  -13.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9795  -14.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9760  -15.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6822  -15.4448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3963  -15.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3998  -14.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6891  -13.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2700  -12.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1017  -15.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1096  -13.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1139  -12.9899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8193  -14.2235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5333  -13.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2423  -14.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9558  -13.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9605  -13.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2458  -12.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5353  -13.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2368  -15.0501    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.2472  -11.7731    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.6914  -12.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2681  -12.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0615  -12.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6370  -12.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4247  -11.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6313  -11.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0503  -11.6134    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
 20 23  1  0
 10 24  1  0
 24 25  1  0
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538973

   ---

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: 448.39

Molecular Weight (Monoisotopic): 447.1480

AlogP: 4.82

#Rotatable Bonds: 4

Polar Surface Area: 70.23

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.44

CX Basic pKa: 10.25

CX LogP: 3.31

CX LogD: 0.60

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.62

Np Likeness Score: -1.15

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