2-amino-5-(4-(2-(3,5-difluorophenyl)-2-hydroxyacetamido)-2-methylphenyl)nicotinic acid

ID: ALA4865268

PubChem CID: 156117898

Max Phase: Preclinical

Molecular Formula: C21H17F2N3O4

Molecular Weight: 413.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(NC(=O)C(O)c2cc(F)cc(F)c2)ccc1-c1cnc(N)c(C(=O)O)c1

Standard InChI:  InChI=1S/C21H17F2N3O4/c1-10-4-15(26-20(28)18(27)11-5-13(22)8-14(23)6-11)2-3-16(10)12-7-17(21(29)30)19(24)25-9-12/h2-9,18,27H,1H3,(H2,24,25)(H,26,28)(H,29,30)

Standard InChI Key:  GTVXRXBVDPTLON-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   31.1674  -15.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1663  -16.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8743  -16.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5840  -16.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5811  -15.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8725  -15.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4617  -15.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4628  -14.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7558  -13.8958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0473  -14.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0501  -15.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7576  -15.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3389  -13.8972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3420  -15.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6328  -15.1325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3451  -16.3556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2923  -16.7573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9994  -16.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7077  -16.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9981  -15.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4148  -16.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1219  -16.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8284  -16.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8276  -15.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1143  -15.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4106  -15.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4582  -16.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5366  -16.7530    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.1101  -14.3026    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   34.7090  -17.5722    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
  4 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  2 27  1  0
 23 28  1  0
 25 29  1  0
 19 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4865268

   ---

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: 413.38

Molecular Weight (Monoisotopic): 413.1187

AlogP: 3.29

#Rotatable Bonds: 5

Polar Surface Area: 125.54

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.59

CX Basic pKa: 6.41

CX LogP: 2.04

CX LogD: 1.07

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: -0.85

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