syn-6-(8-Fluoronaphthalen-2-yl)-2-oxo-1,2-dihydropyridin-3-yl)-3-methylbutyl)thiazolidine-2,4-dione

ID: ALA4763179

PubChem CID: 137490797

Max Phase: Preclinical

Molecular Formula: C23H21FN2O3S

Molecular Weight: 424.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](C[C@H]1SC(=O)NC1=O)c1ccc(-c2ccc3cccc(F)c3c2)[nH]c1=O

Standard InChI:  InChI=1S/C23H21FN2O3S/c1-12(2)16(11-20-22(28)26-23(29)30-20)15-8-9-19(25-21(15)27)14-7-6-13-4-3-5-18(24)17(13)10-14/h3-10,12,16,20H,11H2,1-2H3,(H,25,27)(H,26,28,29)/t16-,20+/m0/s1

Standard InChI Key:  JIWDAZJAHHBDEK-OXJNMPFZSA-N

Molfile:  

 
     RDKit          2D

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   22.2994   -4.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0047   -4.8949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7100   -4.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7100   -3.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0047   -3.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5884   -3.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5923   -4.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4153   -4.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.8269   -4.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8256   -5.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5347   -6.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2454   -5.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2427   -4.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5331   -4.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8830   -3.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1730   -3.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8876   -4.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5307   -3.6712    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.5830   -2.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2880   -2.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0370   -2.3576    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.5798   -1.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1665   -1.0416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3684   -1.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7574   -0.6742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3931   -1.8267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
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  4  5  2  0
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 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  6
 19 20  1  0
 19 21  1  0
 18 22  1  0
  7 23  1  0
 24 23  1  6
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 24 28  1  0
 28 29  2  0
 26 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4763179

   ---

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: 424.50

Molecular Weight (Monoisotopic): 424.1257

AlogP: 4.82

#Rotatable Bonds: 5

Polar Surface Area: 79.03

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.62

CX Basic pKa: ┄

CX LogP: 3.77

CX LogD: 2.95

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.62

Np Likeness Score: -0.65

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