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

ID: ALA4745252

PubChem CID: 162648855

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(OC3CCNCC3)c2)c1

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

Standard InChI Key:  CNMYDAVATJWRII-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   16.6478  -17.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6467  -18.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3547  -18.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0644  -18.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0616  -17.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3529  -17.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3564  -19.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6470  -20.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6464  -20.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3546  -21.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0647  -20.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0618  -20.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7677  -17.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4770  -17.6102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7646  -16.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3554  -22.1136    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.1831  -17.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8908  -17.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5965  -17.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5938  -16.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8796  -15.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1769  -16.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8918  -18.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6001  -18.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6011  -19.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3072  -18.4236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7738  -21.2899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4801  -20.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1837  -21.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8879  -20.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8895  -20.0641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1806  -19.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4702  -20.0648    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:

   

   ALA4745252

   ---

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: 9.82

CX LogP: 1.97

CX LogD: 1.97

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: -0.70

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