Rac-2-(5-Ethylthiophen-2-yl)-6-fluoro-3-(4-fluorobenzyl)-2,3-dihydroquinazolin-4(1H)-one

ID: ALA3322091

Cas Number: 1542098-94-1

PubChem CID: 72720908

Max Phase: Preclinical

Molecular Formula: C21H18F2N2OS

Molecular Weight: 384.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(C2Nc3ccc(F)cc3C(=O)N2Cc2ccc(F)cc2)s1

Standard InChI:  InChI=1S/C21H18F2N2OS/c1-2-16-8-10-19(27-16)20-24-18-9-7-15(23)11-17(18)21(26)25(20)12-13-3-5-14(22)6-4-13/h3-11,20,24H,2,12H2,1H3

Standard InChI Key:  SVXVTSKHYHQIPJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.9277  -10.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9265  -11.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6414  -12.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395  -10.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3549  -10.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3583  -11.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0735  -12.1211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7900  -11.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7865  -10.8778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667  -10.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5056  -12.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0622   -9.6392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5945  -12.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4015  -13.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105  -12.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2560  -11.7795    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6305  -12.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1185  -12.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4997  -10.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4971   -9.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2127   -9.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2105   -8.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4942   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7788   -8.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7844   -9.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4906   -7.1665    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132  -10.4750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 10 12  2  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 11  1  0
 15 17  1  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3322091

   2-(5-Ethylthiophene-2-yl)-6-fluoro-3-(4-fluorobenzyl)-2,3-dihydroquinazoline-4(1H)-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: 384.45

Molecular Weight (Monoisotopic): 384.1108

AlogP: 5.36

#Rotatable Bonds: 4

Polar Surface Area: 32.34

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.11

CX Basic pKa: ┄

CX LogP: 6.29

CX LogD: 6.29

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -1.49

References

1. Carney DW, Nelson CD, Ferris BD, Stevens JP, Lipovsky A, Kazakov T, DiMaio D, Atwood WJ, Sello JK..  (2014)  Structural optimization of a retrograde trafficking inhibitor that protects cells from infections by human polyoma- and papillomaviruses.,  22  (17): [PMID:25087050] [10.1016/j.bmc.2014.06.053]

Source

Source(1):

• Scientific Literature