1-{4-[6-Amino-5-(4-chlorophenyl)pyridin-3-yl]phenyl}cyclopentanecarboxylic acid

ID: ALA4778859

PubChem CID: 126480545

Max Phase: Preclinical

Molecular Formula: C23H21ClN2O2

Molecular Weight: 392.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncc(-c2ccc(C3(C(=O)O)CCCC3)cc2)cc1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C23H21ClN2O2/c24-19-9-5-16(6-10-19)20-13-17(14-26-21(20)25)15-3-7-18(8-4-15)23(22(27)28)11-1-2-12-23/h3-10,13-14H,1-2,11-12H2,(H2,25,26)(H,27,28)

Standard InChI Key:  VHQILBJBMFWZGW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.3080   -4.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6472   -5.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9049   -5.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -5.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9741   -5.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1416   -2.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1405   -2.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8485   -3.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5582   -2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5553   -2.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8467   -1.7166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2630   -3.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2630   -4.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9705   -4.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6785   -4.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6746   -3.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9665   -2.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2615   -1.7106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4343   -3.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7267   -2.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0191   -3.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0180   -4.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7304   -4.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4350   -4.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3874   -4.5738    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6026   -4.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951   -4.5776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6022   -3.3515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
 10 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  7 19  1  0
 15 25  1  0
 22  1  1  0
  1 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4778859

   ---

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: 392.89

Molecular Weight (Monoisotopic): 392.1292

AlogP: 5.55

#Rotatable Bonds: 4

Polar Surface Area: 76.21

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.43

CX Basic pKa: 7.01

CX LogP: 3.92

CX LogD: 3.39

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -0.33

References

1. Dow RL,Ammirati M,Bagley SW,Bhattacharya SK,Buckbinder L,Cortes C,El-Kattan AF,Ford K,Freeman GB,Guimarães CRW,Liu S,Niosi M,Skoura A,Tess D.  (2018)  2-Aminopyridine-Based Mitogen-Activated Protein Kinase Kinase Kinase Kinase 4 (MAP4K4) Inhibitors: Assessment of Mechanism-Based Safety.,  61  (7): [PMID:29570292] [10.1021/acs.jmedchem.8b00152]

Source

Source(1):

• Scientific Literature