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

ID: ALA4547569

PubChem CID: 155553285

Max Phase: Preclinical

Molecular Formula: C22H21BrN2O3

Molecular Weight: 441.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=C(C(=O)Nc2ccccc2C)C(c2ccc(Br)o2)C2=C(CCCC2=O)N1

Standard InChI:  InChI=1S/C22H21BrN2O3/c1-12-6-3-4-7-14(12)25-22(27)19-13(2)24-15-8-5-9-16(26)20(15)21(19)17-10-11-18(23)28-17/h3-4,6-7,10-11,21,24H,5,8-9H2,1-2H3,(H,25,27)

Standard InChI Key:  VJJZMDYDXDGRAA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   12.5674  -28.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5674  -29.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2768  -29.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2768  -28.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9862  -28.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9828  -29.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6889  -29.9768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4031  -29.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4066  -28.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6959  -28.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2768  -27.5080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1085  -29.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1164  -28.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1207  -27.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8261  -28.7555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5401  -28.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2490  -28.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9625  -28.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9673  -27.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2526  -27.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5420  -27.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2435  -29.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6967  -27.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3592  -27.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1089  -26.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2916  -26.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0370  -27.0349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8131  -25.5959    0.0000 Br  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  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 23  1  0
 10 23  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4547569

   ---

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: 441.33

Molecular Weight (Monoisotopic): 440.0736

AlogP: 4.96

#Rotatable Bonds: 3

Polar Surface Area: 71.34

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.16

CX LogD: 3.16

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -1.68

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