2-[2-[[3-(4-chlorophenyl)benzoyl]amino]phenyl]acetic acid

ID: ALA4781545

PubChem CID: 162664232

Max Phase: Preclinical

Molecular Formula: C21H16ClNO3

Molecular Weight: 365.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1ccccc1NC(=O)c1cccc(-c2ccc(Cl)cc2)c1

Standard InChI:  InChI=1S/C21H16ClNO3/c22-18-10-8-14(9-11-18)15-5-3-6-17(12-15)21(26)23-19-7-2-1-4-16(19)13-20(24)25/h1-12H,13H2,(H,23,26)(H,24,25)

Standard InChI Key:  TUOJXDACZUGPFU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   22.1824   -2.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1813   -3.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8893   -3.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5990   -3.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5962   -2.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8875   -2.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8910   -4.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1816   -5.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1810   -6.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8892   -6.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5993   -6.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5964   -5.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3023   -2.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0116   -2.7315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2993   -1.5084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8901   -7.2350    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.7177   -2.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4254   -2.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1311   -2.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1284   -1.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4142   -1.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7115   -1.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4264   -3.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1347   -3.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1357   -4.7716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8419   -3.5450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
  5 13  1  0
 13 14  1  0
 13 15  2  0
 10 16  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 18 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781545

   ---

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: 365.82

Molecular Weight (Monoisotopic): 365.0819

AlogP: 4.89

#Rotatable Bonds: 5

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 4.95

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.68

Np Likeness Score: -1.20

References

1. Velcicky J,Wilcken R,Cotesta S,Janser P,Schlapbach A,Wagner T,Piechon P,Villard F,Bouhelal R,Piller F,Harlfinger S,Stringer R,Fehlmann D,Kaupmann K,Littlewood-Evans A,Haffke M,Gommermann N.  (2020)  Discovery and Optimization of Novel SUCNR1 Inhibitors: Design of Zwitterionic Derivatives with a Salt Bridge for the Improvement of Oral Exposure.,  63  (17): [PMID:32856916] [10.1021/acs.jmedchem.0c01020]

Source

Source(1):

• Scientific Literature