2-(2-(4'-Chloro-3'-(piperidin-3-yloxy)-[1,1'-biphenyl]-3-carboxamido)phenyl)acetic acid

ID: ALA4759141

PubChem CID: 162658251

Max Phase: Preclinical

Molecular Formula: C26H25ClN2O4

Molecular Weight: 464.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1ccccc1NC(=O)c1cccc(-c2ccc(Cl)c(OC3CCCNC3)c2)c1

Standard InChI:  InChI=1S/C26H25ClN2O4/c27-22-11-10-18(14-24(22)33-21-8-4-12-28-16-21)17-6-3-7-20(13-17)26(32)29-23-9-2-1-5-19(23)15-25(30)31/h1-3,5-7,9-11,13-14,21,28H,4,8,12,15-16H2,(H,29,32)(H,30,31)

Standard InChI Key:  KUFQHOICNXMBSD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   23.5857  -17.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5845  -18.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2926  -19.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0023  -18.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9994  -17.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2908  -17.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2943  -19.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5848  -20.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5843  -21.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2924  -21.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0026  -21.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9996  -20.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7056  -17.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4148  -17.8041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7025  -16.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2933  -22.3076    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.1210  -17.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8287  -17.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5343  -17.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5317  -16.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8175  -16.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1147  -16.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8297  -18.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5379  -19.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5390  -19.8443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2451  -18.6176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7116  -21.4839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4180  -21.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1216  -21.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8258  -21.0756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8273  -20.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1185  -19.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4080  -20.2587    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
  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
 11 27  1  0
 27 28  1  0
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759141

   ---

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: 464.95

Molecular Weight (Monoisotopic): 464.1503

AlogP: 5.02

#Rotatable Bonds: 7

Polar Surface Area: 87.66

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.77

CX Basic pKa: 9.42

CX LogP: 2.42

CX LogD: 2.42

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: -0.82

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