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

ID: ALA4759743

PubChem CID: 162657481

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-/m0/s1

Standard InChI Key:  ZGPQAVBMVJZKPG-LBPRGKRZSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   28.4293  -19.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2899  -17.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2887  -18.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0035  -18.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7199  -18.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7171  -17.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0017  -16.8745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.4315  -18.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4314  -19.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1457  -19.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8605  -19.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8566  -18.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1418  -18.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4300  -16.8685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5758  -18.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8614  -18.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1471  -18.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1460  -19.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8651  -19.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5765  -19.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5762  -19.7589    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.7155  -19.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0003  -19.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2866  -19.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9989  -20.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7168  -18.5227    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  6
M  END

Alternative Forms

1. Parent:

   

   ALA4759743

   ---

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