N1-benzyl-4-fluoro-N3-phenylisophthalamide

ID: ALA5286808

Max Phase: Preclinical

Molecular Formula: C21H17FN2O2

Molecular Weight: 348.38

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccccc1)c1ccc(F)c(C(=O)Nc2ccccc2)c1

Standard InChI:  InChI=1S/C21H17FN2O2/c22-19-12-11-16(20(25)23-14-15-7-3-1-4-8-15)13-18(19)21(26)24-17-9-5-2-6-10-17/h1-13H,14H2,(H,23,25)(H,24,26)

Standard InChI Key:  BWDXKXJTDKUEGJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -1.7851    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0707   -0.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0707   -1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851   -1.4450    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3542   -1.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3558   -0.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702    0.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7846   -0.2037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4991    0.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2135   -0.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2135   -1.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299   -1.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9281    0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3561    0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4995   -0.2041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2140    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9239   -0.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401    1.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9257    1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2140    1.0333    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
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  4  6  2  0
  6  7  1  0
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  9 18  2  0
  8 19  1  0
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 24 23  1  0
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 21 26  2  0
 26 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286808

   ---

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: 348.38

Molecular Weight (Monoisotopic): 348.1274

AlogP: 4.01

#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: 13.76

CX Basic pKa: ┄

CX LogP: 4.01

CX LogD: 4.01

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.73

Np Likeness Score: -1.67

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