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

ID: ALA4757838

PubChem CID: 162656122

Max Phase: Preclinical

Molecular Formula: C27H19FN2O4

Molecular Weight: 454.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)/C(=C/C(Cc2ccccc2)c2ccc(-c3ccc4cccc(F)c4c3)[nH]c2=O)O1

Standard InChI:  InChI=1S/C27H19FN2O4/c28-22-8-4-7-17-9-10-18(14-21(17)22)23-12-11-20(25(31)29-23)19(13-16-5-2-1-3-6-16)15-24-26(32)30-27(33)34-24/h1-12,14-15,19H,13H2,(H,29,31)(H,30,32,33)/b24-15-

Standard InChI Key:  IPTLDDDTNVLCOY-IWIPYMOSSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   16.7565  -11.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7565  -11.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4618  -12.3157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1671  -11.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1671  -11.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.0455  -10.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0494  -12.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8724  -12.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8699  -13.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5762  -13.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5771  -11.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2840  -12.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2828  -13.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9918  -13.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7026  -13.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.9902  -11.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9879  -11.0920    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.0401   -9.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3297   -9.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2346   -8.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4342   -8.4888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0302   -9.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5811   -9.8028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2181   -9.2901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8368   -8.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3403  -11.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9241  -11.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1068  -11.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6906  -12.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0906  -13.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9110  -13.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3236  -12.5105    0.0000 C   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
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 13 12  2  0
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  4  9  1  0
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 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 18 19  1  0
  7 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
 24 26  2  0
 22 27  2  0
  7 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4757838

   ---

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: 454.46

Molecular Weight (Monoisotopic): 454.1329

AlogP: 4.81

#Rotatable Bonds: 5

Polar Surface Area: 88.26

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.15

CX Basic pKa: ┄

CX LogP: 3.99

CX LogD: 2.80

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.42

Np Likeness Score: -0.41

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