(R)-2-amino-5-(4-(2-(3,5-difluorophenyl)-2-hydroxyacetamido)-2-methylphenyl)-N-methylnicotinamide

ID: ALA4875875

PubChem CID: 156118285

Max Phase: Preclinical

Molecular Formula: C22H20F2N4O3

Molecular Weight: 426.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cc(-c2ccc(NC(=O)[C@H](O)c3cc(F)cc(F)c3)cc2C)cnc1N

Standard InChI:  InChI=1S/C22H20F2N4O3/c1-11-5-16(28-22(31)19(29)12-6-14(23)9-15(24)7-12)3-4-17(11)13-8-18(21(30)26-2)20(25)27-10-13/h3-10,19,29H,1-2H3,(H2,25,27)(H,26,30)(H,28,31)/t19-/m1/s1

Standard InChI Key:  XMJPZNCMRRFABT-LJQANCHMSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    5.0627   -2.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0615   -3.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7696   -4.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4793   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4764   -2.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7678   -2.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -2.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3581   -1.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6511   -1.2954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454   -2.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6529   -2.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2342   -1.2967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373   -2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281   -2.5320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404   -3.7551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342   -4.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1876   -4.1568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8947   -3.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6030   -4.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8934   -2.9299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3101   -3.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0171   -4.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7237   -3.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7229   -2.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0096   -2.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3059   -2.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3535   -4.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4319   -4.1526    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.0054   -1.7022    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.6043   -4.9718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  1  7  1  0
 10 13  1  0
 14 15  2  0
 14 16  1  0
 11 14  1  0
 16 17  1  0
  4 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  2 28  1  0
 24 29  1  0
 26 30  1  0
 20 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4875875

   ---

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: 426.42

Molecular Weight (Monoisotopic): 426.1503

AlogP: 2.95

#Rotatable Bonds: 5

Polar Surface Area: 117.34

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.01

CX Basic pKa: 5.02

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: -1.05

References

1. Calvo V, Surguladze D, Li AH, Surman MD, Malibhatla S, Bandaru M, Jonnalagadda SK, Adarasandi R, Velmala M, Singireddi DRP, Velpuri M, Nareddy BR, Sastry V, Mandati C, Guguloth R, Siddiqui S, Patil BS, Chad E, Wolfley J, Gasparek J, Feldman K, Betzenhauser M, Wiens B, Koszelak-Rosenblum M, Zhu G, Du H, Rigby AC, Mulvihill MJ..  (2021)  Discovery of 2-amino-3-amido-5-aryl-pyridines as highly potent, orally bioavailable, and efficacious PERK kinase inhibitors.,  43  [PMID:33895276] [10.1016/j.bmcl.2021.128058]

Source

Source(1):

• Scientific Literature