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

ID: ALA4483489

PubChem CID: 155540536

Max Phase: Preclinical

Molecular Formula: C22H24N2O3

Molecular Weight: 364.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(NC(=O)C2CC2)cc(-c2ccc(C3CCNCC3)cc2)c1

Standard InChI:  InChI=1S/C22H24N2O3/c25-21(17-5-6-17)24-20-12-18(11-19(13-20)22(26)27)15-3-1-14(2-4-15)16-7-9-23-10-8-16/h1-4,11-13,16-17,23H,5-10H2,(H,24,25)(H,26,27)

Standard InChI Key:  WMNNSGJASLLONL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   34.4527  -14.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4515  -15.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1596  -16.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8692  -15.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8664  -14.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1578  -14.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1613  -16.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4518  -17.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4513  -18.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1594  -18.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8696  -18.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8666  -17.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1639  -19.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4549  -19.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4538  -20.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1601  -20.9007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8692  -20.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8719  -19.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5726  -14.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2818  -14.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5695  -13.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7449  -14.3670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0373  -14.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3295  -14.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0375  -15.5930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9207  -13.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5123  -14.3686    0.0000 C   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
 26 24  1  0
 27 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483489

   ---

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: 364.45

Molecular Weight (Monoisotopic): 364.1787

AlogP: 3.87

#Rotatable Bonds: 5

Polar Surface Area: 78.43

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.84

CX Basic pKa: 10.07

CX LogP: 0.93

CX LogD: 0.93

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -0.91

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