Diethyl {2-benzyl-5-[(3-(3-fluorobenzoyl)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)methyl]isoxazolidin-3-yl}phosphonate

ID: ALA4098905

PubChem CID: 137662294

Max Phase: Preclinical

Molecular Formula: C30H31FN3O7P

Molecular Weight: 595.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OCC)C1CC(Cn2c(=O)n(C(=O)c3cccc(F)c3)c(=O)c3ccccc32)ON1Cc1ccccc1

Standard InChI:  InChI=1S/C30H31FN3O7P/c1-3-39-42(38,40-4-2)27-18-24(41-33(27)19-21-11-6-5-7-12-21)20-32-26-16-9-8-15-25(26)29(36)34(30(32)37)28(35)22-13-10-14-23(31)17-22/h5-17,24,27H,3-4,18-20H2,1-2H3

Standard InChI Key:  RMDHLFBXEZDNSQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 42 46  0  0  0  0  0  0  0  0999 V2000
   11.4191   -5.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5471  -11.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6890  -12.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5878   -5.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4215   -5.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8360   -5.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3590  -11.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3865  -10.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5868   -7.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6879   -9.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7075   -6.3462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9851   -9.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2892   -8.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2089  -11.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8412  -11.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8742   -6.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5373   -8.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1283   -6.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5692  -11.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2592   -5.9424    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7075   -7.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5449   -6.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8326   -7.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9996   -8.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8716   -9.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9996   -5.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5452   -7.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5064  -12.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9996   -7.5755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8373   -8.2454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1242   -7.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5748   -9.7007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2916   -7.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8758   -7.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0621  -10.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1595  -10.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2943   -6.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9982   -5.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3977   -9.7916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1687   -8.9950    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.4173   -7.5807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2005   -9.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 21 11  1  0
 29 24  1  0
 23 27  2  0
 18 31  2  0
 40 32  1  0
  6 18  1  0
 21 41  2  0
  1  5  2  0
 26 38  2  0
 15  7  2  0
 11 26  1  0
  9 33  1  0
  4 16  2  0
 16 34  1  0
 39 42  1  0
 39 35  1  0
 25  8  1  0
  7  2  1  0
 22 20  1  0
 13 24  1  0
 40 30  2  0
 10 25  1  0
 32 36  1  0
 34  9  2  0
 22  6  2  0
 37 26  1  0
  3 28  2  0
 33 29  1  0
 40 10  1  0
 27 22  1  0
 13 17  1  0
 14  3  1  0
 35  2  1  0
 12 40  1  0
 29 21  1  0
 17 12  1  0
 33 37  2  0
  1 18  1  0
 28 15  1  0
 37  4  1  0
  2 14  2  0
 42 13  1  0
 11  1  1  0
 36 19  1  0
 31 23  1  0
 12 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098905

   ---

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: 595.56

Molecular Weight (Monoisotopic): 595.1884

AlogP: 4.79

#Rotatable Bonds: 10

Polar Surface Area: 109.07

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.77

CX LogD: 4.77

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.24

Np Likeness Score: -0.66

References

1. Piotrowska DG, Andrei G, Schols D, Snoeck R, Łysakowska M..  (2017)  Synthesis, anti-varicella-zoster virus and anti-cytomegalovirus activity of quinazoline-2,4-diones containing isoxazolidine and phosphonate substructures.,  126  [PMID:27750154] [10.1016/j.ejmech.2016.10.002]

Source

Source(1):

• Scientific Literature