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

ID: ALA4793121

PubChem CID: 162671261

Max Phase: Preclinical

Molecular Formula: C20H17ClN2O2

Molecular Weight: 352.82

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H17ClN2O2/c21-17-8-6-15(7-9-17)18-11-16(12-23-20(18)22)14-4-1-13(2-5-14)3-10-19(24)25/h1-2,4-9,11-12H,3,10H2,(H2,22,23)(H,24,25)

Standard InChI Key:  CPYBMXWQSDLGOO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   27.8468   -4.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6804   -1.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6793   -2.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3873   -3.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0970   -2.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0941   -1.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3855   -1.5598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8018   -3.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8017   -4.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5093   -4.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2173   -4.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2134   -3.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5053   -2.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8003   -1.5538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9731   -3.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2654   -2.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5579   -3.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5568   -4.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2692   -4.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9738   -4.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9262   -4.4169    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.1398   -4.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4314   -4.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7244   -4.0073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4301   -5.2342    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:

   

   ALA4793121

   ---

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: 352.82

Molecular Weight (Monoisotopic): 352.0979

AlogP: 4.67

#Rotatable Bonds: 5

Polar Surface Area: 76.21

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.66

CX Basic pKa: 7.01

CX LogP: 2.87

CX LogD: 2.35

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -0.31

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