{4-[6-Amino-5-(4-chlorophenyl)pyridin-3-yl]phenoxy}acetic acid

ID: ALA4779507

PubChem CID: 162663262

Max Phase: Preclinical

Molecular Formula: C19H15ClN2O3

Molecular Weight: 354.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncc(-c2ccc(OCC(=O)O)cc2)cc1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C19H15ClN2O3/c20-15-5-1-13(2-6-15)17-9-14(10-22-19(17)21)12-3-7-16(8-4-12)25-11-18(23)24/h1-10H,11H2,(H2,21,22)(H,23,24)

Standard InChI Key:  TYUVOSCOPCOESA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   27.7890  -11.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6226   -8.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6215   -9.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3295   -9.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0392   -9.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0364   -8.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3277   -8.2707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7440   -9.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7440  -10.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4515  -11.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1595  -10.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1556   -9.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4475   -9.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7425   -8.2647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9153   -9.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2077   -9.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5001   -9.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4990  -10.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2114  -11.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9160  -10.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8684  -11.1278    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.0820  -10.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3736  -11.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6666  -10.7181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3723  -11.9451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  5  8  1  0
  6 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  3 15  1  0
 11 21  1  0
 18  1  1  0
  1 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4779507

   ---

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: 354.79

Molecular Weight (Monoisotopic): 354.0771

AlogP: 4.11

#Rotatable Bonds: 5

Polar Surface Area: 85.44

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.80

CX Basic pKa: 6.03

CX LogP: 2.11

CX LogD: 0.85

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: -0.67

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