(R,Z)-4-(furan-2-yl(hydroxy)methylene)-5-(3-phenoxyphenyl)-1-(pyridin-3-ylmethyl)pyrrolidine-2,3-dione

ID: ALA604091

PubChem CID: 986480

Max Phase: Preclinical

Molecular Formula: C27H20N2O5

Molecular Weight: 452.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ZINC 00633950 | CHEMBL604091|ZINC 00633950|BDBM50481402

Canonical SMILES:  O=C1C(=O)N(Cc2cccnc2)[C@H](c2cccc(Oc3ccccc3)c2)/C1=C(/O)c1ccco1

Standard InChI:  InChI=1S/C27H20N2O5/c30-25(22-12-6-14-33-22)23-24(29(27(32)26(23)31)17-18-7-5-13-28-16-18)19-8-4-11-21(15-19)34-20-9-2-1-3-10-20/h1-16,24,30H,17H2/b25-23-/t24-/m1/s1

Standard InChI Key:  VJDJKGFSWOCZNX-QQYUXEJHSA-N

Molfile:  

     RDKit          2D

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    3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3967    0.9602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3031    3.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9295    3.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9319    2.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0031    3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2947    3.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938    5.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919    5.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8928    3.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5923    6.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5943    3.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6137   -3.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143   -5.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938   -6.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972   -7.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211   -8.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6416   -7.3872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382   -5.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  8  2  0
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  3  4  1  0
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  4  5  1  0
 19 20  2  0
 20 15  1  0
  8 10  1  0
 19 21  1  0
 10 11  1  0
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  5  1  1  0
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  1  2  1  0
  1  6  2  0
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 26 24  2  0
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 12 13  2  0
  5 28  1  0
 13 14  1  0
 28 29  1  0
 14 10  2  0
 29 30  2  0
  2  7  2  0
 30 31  1  0
  4 15  1  6
 31 32  2  0
  2  3  1  0
 32 33  1  0
 15 16  2  0
 33 34  2  0
 34 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA604091

   (2R)-3-(furan-2-carbonyl)-4-hydroxy-2-(3-phenoxyphenyl)-1-(pyridin-3-ylmethyl)-2H-pyrrol-5-one

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: 452.47

Molecular Weight (Monoisotopic): 452.1372

AlogP: 5.09

#Rotatable Bonds: 6

Polar Surface Area: 92.87

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.37

CX Basic pKa: 5.01

CX LogP: 3.22

CX LogD: 1.37

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.25

Np Likeness Score: -1.20

References

1. Podvinec M, Lim SP, Schmidt T, Scarsi M, Wen D, Sonntag LS, Sanschagrin P, Shenkin PS, Schwede T..  (2010)  Novel inhibitors of dengue virus methyltransferase: discovery by in vitro-driven virtual screening on a desktop computer grid.,  53  (4): [PMID:20108931] [10.1021/jm900776m]

Source

Source(1):

• Scientific Literature