2-(4'-Chloro-[1,1'-biphenyl]-3-carboxamido)benzoic acid

ID: ALA4740249

PubChem CID: 162644696

Max Phase: Preclinical

Molecular Formula: C20H14ClNO3

Molecular Weight: 351.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1C(=O)O)c1cccc(-c2ccc(Cl)cc2)c1

Standard InChI:  InChI=1S/C20H14ClNO3/c21-16-10-8-13(9-11-16)14-4-3-5-15(12-14)19(23)22-18-7-2-1-6-17(18)20(24)25/h1-12H,(H,22,23)(H,24,25)

Standard InChI Key:  KRHLECJYYZUAHL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   15.4138   -2.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4126   -3.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1207   -4.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8303   -3.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8275   -2.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1189   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1224   -5.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4129   -5.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4124   -6.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1205   -6.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8307   -6.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8277   -5.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5337   -2.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2429   -2.9791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5306   -1.7560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1214   -7.4826    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.9491   -2.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6568   -2.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3624   -2.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3598   -1.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6456   -1.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9428   -1.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6578   -3.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9506   -4.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3660   -4.2021    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  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740249

   ---

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: 351.79

Molecular Weight (Monoisotopic): 351.0662

AlogP: 4.96

#Rotatable Bonds: 4

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: 3.55

CX Basic pKa: ┄

CX LogP: 5.62

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -1.16

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