2-(2-(3-cyano-4-(4-fluorophenyl)-6-(thiophen-2-yl)pyridin-2-ylthio)acetamido)acetic acid

ID: ALA4159754

PubChem CID: 9497209

Max Phase: Preclinical

Molecular Formula: C20H14FN3O3S2

Molecular Weight: 427.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c(-c2ccc(F)cc2)cc(-c2cccs2)nc1SCC(=O)NCC(=O)O

Standard InChI:  InChI=1S/C20H14FN3O3S2/c21-13-5-3-12(4-6-13)14-8-16(17-2-1-7-28-17)24-20(15(14)9-22)29-11-18(25)23-10-19(26)27/h1-8H,10-11H2,(H,23,25)(H,26,27)

Standard InChI Key:  JARLZQQNQKOMSB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.2888   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9969   -4.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7065   -3.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7037   -2.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9951   -2.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4114   -4.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4113   -4.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1188   -5.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8269   -4.9514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8230   -4.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1149   -3.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5822   -2.5012    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.1113   -2.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1062   -2.0884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1197   -6.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5286   -3.7178    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.2384   -4.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9440   -3.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6537   -4.1156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9398   -2.8934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3594   -3.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3552   -2.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0608   -2.4740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6454   -2.4812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4601   -6.6585    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.7135   -7.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5307   -7.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7823   -6.6571    0.0000 C   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
  4  7  1  0
  1 13  1  0
 12 14  1  0
 14 15  3  0
  9 16  1  0
 11 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 16 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4159754

   [({[3-Cyano-4-(4-fluorophenyl)-6-(2-thienyl)-2-pyridinyl]sulfanyl}acetyl)amino]acetic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 427.48

Molecular Weight (Monoisotopic): 427.0461

AlogP: 3.78

#Rotatable Bonds: 7

Polar Surface Area: 103.08

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.05

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 0.03

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -2.18

References

1. Xiong H, Han J, Wang J, Lu W, Wang C, Chen Y, Fulin Lian, Zhang N, Liu YC, Zhang C, Ding H, Jiang H, Lu W, Luo C, Zhou B..  (2018)  Discovery of 1,8-acridinedione derivatives as novel GCN5 inhibitors via high throughput screening.,  151  [PMID:29665527] [10.1016/j.ejmech.2018.02.005]

Source

Source(1):

• Scientific Literature