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

ID: ALA4741143

PubChem CID: 162646654

Max Phase: Preclinical

Molecular Formula: C23H20ClN3

Molecular Weight: 373.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CC1(c2ccc(-c3cnc(N)c(-c4ccc(Cl)cc4)c3)cc2)CCCC1

Standard InChI:  InChI=1S/C23H20ClN3/c24-20-9-5-17(6-10-20)21-13-18(14-27-22(21)26)16-3-7-19(8-4-16)23(15-25)11-1-2-12-23/h3-10,13-14H,1-2,11-12H2,(H2,26,27)

Standard InChI Key:  KMYJNKQZFICCIK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   15.8490  -20.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1882  -21.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4458  -21.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2659  -21.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5150  -21.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6825  -18.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6814  -18.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3894  -19.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0991  -18.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0963  -18.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3877  -17.7055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8039  -19.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8039  -20.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5114  -20.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2195  -20.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2155  -19.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5074  -18.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8024  -17.6995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9753  -19.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2676  -18.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5600  -19.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5590  -20.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2713  -20.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9760  -20.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9283  -20.5626    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.1435  -20.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4387  -19.7505    0.0000 N   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  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741143

   ---

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: 373.89

Molecular Weight (Monoisotopic): 373.1346

AlogP: 5.99

#Rotatable Bonds: 3

Polar Surface Area: 62.70

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.01

CX LogP: 5.64

CX LogD: 5.62

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.55

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