(R)-4-Benzyl-9-hydroxy-2-(2-methoxyethyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic Acid

ID: ALA4474376

PubChem CID: 155536871

Max Phase: Preclinical

Molecular Formula: C19H20N2O6

Molecular Weight: 372.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COCCN1C[C@@H](Cc2ccccc2)n2cc(C(=O)O)c(=O)c(O)c2C1=O

Standard InChI:  InChI=1S/C19H20N2O6/c1-27-8-7-20-10-13(9-12-5-3-2-4-6-12)21-11-14(19(25)26)16(22)17(23)15(21)18(20)24/h2-6,11,13,23H,7-10H2,1H3,(H,25,26)/t13-/m1/s1

Standard InChI Key:  LWDWGBYGZZWHRU-CYBMUJFWSA-N

Molfile:  

 
     RDKit          2D

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   22.3655   -3.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0749   -4.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0749   -2.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7843   -2.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7808   -3.6319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4870   -4.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2011   -3.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2046   -2.8166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4939   -2.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9186   -2.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6283   -2.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3381   -2.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0478   -2.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4963   -1.5773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6524   -2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0749   -1.5725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6542   -4.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9459   -3.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6554   -4.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4824   -4.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7683   -5.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0597   -4.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3460   -5.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3410   -6.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0555   -6.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7662   -6.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  2  0
  3  6  1  0
  5  4  2  0
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  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
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  9 11  1  0
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 13 14  1  0
 10 15  2  0
  1 16  2  0
  4 17  1  0
  2 18  1  0
 18 19  1  0
 18 20  2  0
  7 21  1  1
 21 22  1  0
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 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474376

   ---

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: 372.38

Molecular Weight (Monoisotopic): 372.1321

AlogP: 1.14

#Rotatable Bonds: 6

Polar Surface Area: 109.07

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.62

CX Basic pKa: ┄

CX LogP: 1.12

CX LogD: -2.22

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: -0.16

References

1. Miyagawa M, Akiyama T, Taoda Y, Takaya K, Takahashi-Kageyama C, Tomita K, Yasuo K, Hattori K, Shano S, Yoshida R, Shishido T, Yoshinaga T, Sato A, Kawai M..  (2019)  Synthesis and SAR Study of Carbamoyl Pyridone Bicycle Derivatives as Potent Inhibitors of Influenza Cap-dependent Endonuclease.,  62  (17): [PMID:31386363] [10.1021/acs.jmedchem.9b00861]

Source

Source(1):

• Scientific Literature