4-chloro-N1-(3-methylbenzyl)-N3-phenylisophthalamide

ID: ALA5287514

Max Phase: Preclinical

Molecular Formula: C22H19ClN2O2

Molecular Weight: 378.86

Names and Identifiers

Canonical SMILES:  Cc1cccc(CNC(=O)c2ccc(Cl)c(C(=O)Nc3ccccc3)c2)c1

Standard InChI:  InChI=1S/C22H19ClN2O2/c1-15-6-5-7-16(12-15)14-24-21(26)17-10-11-20(23)19(13-17)22(27)25-18-8-3-2-4-9-18/h2-13H,14H2,1H3,(H,24,26)(H,25,27)

Standard InChI Key:  QJGUAEWTHPWKAH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -2.1425    1.0334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -0.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -1.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425   -1.4452    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7115   -1.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -0.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131    0.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276   -0.2037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    0.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566   -0.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566   -1.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5731   -1.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2833   -1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2833   -0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5712    0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9977    0.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131    1.0338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7133    0.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569   -0.2041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715    0.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2814   -0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    1.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833    1.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715    1.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 12  2  0
 16 18  1  0
  9 19  2  0
  8 20  1  0
 20  3  2  0
 21  2  1  0
 22 21  1  0
 23 22  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
 22 27  2  0
 27 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287514

   ---

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: 378.86

Molecular Weight (Monoisotopic): 378.1135

AlogP: 4.83

#Rotatable Bonds: 5

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.98

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 4.98

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -1.73

References

1. Orsi DL, Ferrara SJ, Siegel S, Friberg A, Bouché L, Pook E, Lienau P, Bluck JP, Lemke CT, Akcay G, Stellfeld T, Meyer H, Pütter V, Holton SJ, Korr D, Jerchel-Furau I, Pantelidou C, Strathdee CA, Meyerson M, Eis K, Goldstein JT..  (2023)  Discovery and characterization of orally bioavailable 4-chloro-6-fluoroisophthalamides as covalent PPARG inverse-agonists.,  78  [PMID:36542958] [10.1016/j.bmc.2022.117130]

Source

Source(1):

• Scientific Literature