5-(4-Bromobenzamido)-4'-(piperidin-4-yl)-[1,1'-biphenyl]-3-carboxylic acid

ID: ALA4475814

PubChem CID: 155537709

Max Phase: Preclinical

Molecular Formula: C25H23BrN2O3

Molecular Weight: 479.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(NC(=O)c2ccc(Br)cc2)cc(-c2ccc(C3CCNCC3)cc2)c1

Standard InChI:  InChI=1S/C25H23BrN2O3/c26-22-7-5-19(6-8-22)24(29)28-23-14-20(13-21(15-23)25(30)31)17-3-1-16(2-4-17)18-9-11-27-12-10-18/h1-8,13-15,18,27H,9-12H2,(H,28,29)(H,30,31)

Standard InChI Key:  BCSRKJZOOSIKPD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   35.1543  -24.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1532  -25.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8612  -25.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5709  -25.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5680  -24.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8594  -23.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8629  -26.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1535  -26.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1529  -27.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8611  -28.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5712  -27.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5683  -26.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8656  -28.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1565  -29.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1554  -30.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8618  -30.5131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5708  -30.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5736  -29.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2742  -23.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9835  -24.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2711  -23.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4465  -23.9793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7389  -24.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0311  -23.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7391  -25.2053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0345  -23.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3276  -22.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6190  -23.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6218  -23.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3293  -24.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9106  -22.7549    0.0000 Br  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
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 10 13  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 24  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475814

   ---

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: 479.37

Molecular Weight (Monoisotopic): 478.0892

AlogP: 5.53

#Rotatable Bonds: 5

Polar Surface Area: 78.43

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.84

CX Basic pKa: 10.07

CX LogP: 2.77

CX LogD: 2.77

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: -0.79

References

1. Zhang Z, Hao K, Li H, Lu R, Liu C, Zhou M, Li B, Meng Z, Hu Q, Jiang C..  (2019)  Design, synthesis and anti-inflammatory evaluation of 3-amide benzoic acid derivatives as novel P2Y₁₄ receptor antagonists.,  181  [PMID:31376563] [10.1016/j.ejmech.2019.111564]

Source

Source(1):

• Scientific Literature