(Z)-5-(1-(6-(8-fluoronaphthalen-2-yl)-2-oxo-1,2-dihydropyridin-3-yl)-2-methylpropylidene)thiazolidine-2,4-dione

ID: ALA4764161

PubChem CID: 137487342

Max Phase: Preclinical

Molecular Formula: C22H17FN2O3S

Molecular Weight: 408.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)/C(=C1/SC(=O)NC1=O)c1ccc(-c2ccc3cccc(F)c3c2)[nH]c1=O

Standard InChI:  InChI=1S/C22H17FN2O3S/c1-11(2)18(19-21(27)25-22(28)29-19)14-8-9-17(24-20(14)26)13-7-6-12-4-3-5-16(23)15(12)10-13/h3-11H,1-2H3,(H,24,26)(H,25,27,28)/b19-18-

Standard InChI Key:  OJXAVNBFKSWDBP-HNENSFHCSA-N

Molfile:  

 
     RDKit          2D

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   13.9418   -5.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6471   -5.4108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3523   -5.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3523   -4.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6471   -3.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2308   -3.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2347   -5.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0576   -5.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0551   -6.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7614   -6.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7624   -5.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4692   -5.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4680   -6.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1770   -6.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8878   -6.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8850   -5.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1754   -5.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5254   -4.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8154   -3.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5300   -5.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1731   -4.1871    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.2253   -2.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8837   -2.4787    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.6268   -1.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8096   -1.7075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5616   -2.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7858   -2.7431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1034   -1.0391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  7  1  0
  2  8  2  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 13 12  2  0
 12  9  1  0
  4  9  1  0
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 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  7 19  1  0
 19 20  1  0
 19 21  1  0
 18 22  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
  7 23  2  0
 27 28  2  0
 25 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4764161

   ---

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: 408.45

Molecular Weight (Monoisotopic): 408.0944

AlogP: 4.68

#Rotatable Bonds: 3

Polar Surface Area: 79.03

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.19

CX Basic pKa: ┄

CX LogP: 3.10

CX LogD: 1.94

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.62

Np Likeness Score: -0.89

References

1. Zhang X,Zhu B,Guo L,Bakaj I,Rankin M,Ho G,Kauffman J,Lee SP,Norquay L,Macielag MJ.  (2021)  Discovery of a Novel Series of Pyridone-Based EP3 Antagonists for the Treatment of Type 2 Diabetes.,  12  (3): [PMID:33738072] [10.1021/acsmedchemlett.0c00667]

Source

Source(1):

• Scientific Literature