2-(2-(3'-(Aminomethyl)-4'-chloro-[1,1'-biphenyl]-3-carboxamido)phenyl)acetic acid

ID: ALA4743401

PubChem CID: 162646617

Max Phase: Preclinical

Molecular Formula: C22H19ClN2O3

Molecular Weight: 394.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NCc1cc(-c2cccc(C(=O)Nc3ccccc3CC(=O)O)c2)ccc1Cl

Standard InChI:  InChI=1S/C22H19ClN2O3/c23-19-9-8-15(11-18(19)13-24)14-5-3-6-17(10-14)22(28)25-20-7-2-1-4-16(20)12-21(26)27/h1-11H,12-13,24H2,(H,25,28)(H,26,27)

Standard InChI Key:  ZFAJPOLKQKSTMN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   23.8787   -9.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8776  -10.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5856  -11.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2953  -10.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2925   -9.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5838   -9.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5873  -11.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8779  -12.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8773  -13.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5855  -13.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2956  -13.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2927  -12.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9986   -9.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7079   -9.8221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9955   -8.5990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5864  -14.3256    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.4140   -9.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1217   -9.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8274   -9.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8247   -8.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1105   -8.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4078   -8.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1227  -10.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8310  -11.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8320  -11.8622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5382  -10.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0047  -13.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7110  -13.0909    0.0000 N   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
M  END

Alternative Forms

1. Parent:

   

   ALA4743401

   ---

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: 394.86

Molecular Weight (Monoisotopic): 394.1084

AlogP: 4.35

#Rotatable Bonds: 6

Polar Surface Area: 92.42

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.77

CX Basic pKa: 8.95

CX LogP: 1.82

CX LogD: 1.81

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.08

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