5-(3-allyl-5-ethoxy-4-hydroxybenzylidene)-3-(2-fluorophenyl)imidazolidine-2,4-dione

ID: ALA583462

PubChem CID: 45484022

Max Phase: Preclinical

Molecular Formula: C21H19FN2O4

Molecular Weight: 382.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCc1cc(/C=C2\NC(=O)N(c3ccccc3F)C2=O)cc(OCC)c1O

Standard InChI:  InChI=1S/C21H19FN2O4/c1-3-7-14-10-13(12-18(19(14)25)28-4-2)11-16-20(26)24(21(27)23-16)17-9-6-5-8-15(17)22/h3,5-6,8-12,25H,1,4,7H2,2H3,(H,23,27)/b16-11-

Standard InChI Key:  TVVTUTPHXZVBHQ-WJDWOHSUSA-N

Molfile:  

     RDKit          2D

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    7.5516  -12.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2664  -12.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9828  -12.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9800  -11.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2646  -10.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2621  -10.0039    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6931  -10.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4727  -11.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9705  -10.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4951   -9.7535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7063   -9.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8792  -11.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9875   -9.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7900  -10.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1974   -9.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0207   -9.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4281   -8.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0105   -8.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1813   -8.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7776   -8.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7613   -7.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1662   -6.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7462   -6.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4170   -7.5556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2530   -8.9807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6702   -9.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4952   -9.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 12 14  2  0
  6  7  1  0
 10 15  2  0
  3  4  2  0
 15 16  1  0
  5  8  1  0
 16 17  2  0
  8  9  1  0
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  4  5  1  0
 19 20  1  0
  2  3  1  0
 20 21  2  0
 21 16  1  0
  5  6  2  0
 20 22  1  0
  9 10  1  0
 22 23  1  0
 10 11  1  0
 23 24  2  0
 11 12  1  0
 19 25  1  0
 12  8  1  0
 18 26  1  0
  6  1  1  0
 26 27  1  0
  9 13  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA583462

   (5Z)-5-[(3-allyl-5-ethoxy-4-hydroxy-phenyl)methylene]-3-(2-fluorophenyl)imidazolidine-2,4-dione

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: 382.39

Molecular Weight (Monoisotopic): 382.1329

AlogP: 3.76

#Rotatable Bonds: 6

Polar Surface Area: 78.87

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.91

CX Basic pKa: ┄

CX LogP: 3.70

CX LogD: 3.68

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -0.68

References

1. Gupta RK, Thakur TS, Desiraju GR, Tyagi JS..  (2009)  Structure-based design of DevR inhibitor active against nonreplicating Mycobacterium tuberculosis.,  52  (20): [PMID:19827833] [10.1021/jm900358q]

Source

Source(1):

• Scientific Literature