(2R)-2-{4-[6-Amino-5-(4-chlorophenyl)pyridin-3-yl]phenoxy}propanoic acid

ID: ALA4756318

PubChem CID: 162655528

Max Phase: Preclinical

Molecular Formula: C20H17ClN2O3

Molecular Weight: 368.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H](Oc1ccc(-c2cnc(N)c(-c3ccc(Cl)cc3)c2)cc1)C(=O)O

Standard InChI:  InChI=1S/C20H17ClN2O3/c1-12(20(24)25)26-17-8-4-13(5-9-17)15-10-18(19(22)23-11-15)14-2-6-16(21)7-3-14/h2-12H,1H3,(H2,22,23)(H,24,25)/t12-/m1/s1

Standard InChI Key:  ZGPQAVBMVJZKPG-GFCCVEGCSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   40.9436   -3.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.8041   -1.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8029   -2.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5178   -2.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2341   -2.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2313   -1.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5159   -0.8580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.9457   -2.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9456   -3.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6598   -3.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.3746   -3.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.3707   -2.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6559   -2.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9442   -0.8519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.0901   -2.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3757   -2.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6615   -2.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6604   -3.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3794   -3.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0908   -3.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.0902   -3.7422    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   40.2299   -3.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5148   -3.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8011   -3.3287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5134   -4.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.2313   -2.5061    0.0000 C   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
 22 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4756318

   ---

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: 368.82

Molecular Weight (Monoisotopic): 368.0928

AlogP: 4.50

#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: 3.84

CX Basic pKa: 6.03

CX LogP: 2.69

CX LogD: 1.43

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -0.68

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