N-(2-Chloro-5-methoxyphenyl)-2-methyl-5-oxo-4-propyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxamide

ID: ALA4476587

PubChem CID: 155538299

Max Phase: Preclinical

Molecular Formula: C21H25ClN2O3

Molecular Weight: 388.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCC1C(C(=O)Nc2cc(OC)ccc2Cl)=C(C)NC2=C1C(=O)CCC2

Standard InChI:  InChI=1S/C21H25ClN2O3/c1-4-6-14-19(12(2)23-16-7-5-8-18(25)20(14)16)21(26)24-17-11-13(27-3)9-10-15(17)22/h9-11,14,23H,4-8H2,1-3H3,(H,24,26)

Standard InChI Key:  TVBFFVDMWQOGLF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   22.0642   -4.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7736   -4.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7736   -3.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4830   -3.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4795   -4.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1857   -4.8791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8998   -4.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9033   -3.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1926   -3.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7736   -2.4103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6052   -4.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6132   -3.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6175   -2.4242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3228   -3.6578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0368   -3.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7458   -3.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4593   -3.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4640   -2.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7494   -2.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0388   -2.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1950   -2.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9038   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9062   -1.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7403   -4.4844    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.7508   -1.2074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4592   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
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  8  9  2  0
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 21 16  1  0
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 17 25  1  0
 20 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476587

   ---

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: 388.90

Molecular Weight (Monoisotopic): 388.1554

AlogP: 4.59

#Rotatable Bonds: 5

Polar Surface Area: 67.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.37

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: 3.40

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.77

Np Likeness Score: -1.14

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