5-(benzo[d][1,3]dioxol-5-ylmethylene)-1-benzylpyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA3261357

PubChem CID: 2272071

Max Phase: Preclinical

Molecular Formula: C19H14N2O5

Molecular Weight: 350.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)N(Cc2ccccc2)C(=O)/C1=C\c1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C19H14N2O5/c22-17-14(8-13-6-7-15-16(9-13)26-11-25-15)18(23)21(19(24)20-17)10-12-4-2-1-3-5-12/h1-9H,10-11H2,(H,20,22,24)/b14-8-

Standard InChI Key:  AIQAOCWPVYYIGL-ZSOIEALJSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   10.7496   -9.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1582   -8.7913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9754   -8.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3840   -9.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9754  -10.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1582  -10.2095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9324   -9.5004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3840   -8.0822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3840  -10.9144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7496  -10.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9324  -10.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5238  -11.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7066  -11.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2980  -10.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7066  -10.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5238  -10.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2012   -9.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9748  -12.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7221  -11.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6340  -11.0852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8356  -10.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4270  -11.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4270  -10.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6098  -10.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2012  -10.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6098  -11.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  1  7  2  0
  3  8  2  0
  5  9  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 10 11  1  0
  6 10  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 22  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 22 26  2  0
 21 23  2  0
 17 24  1  0
  4 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3261357

   (5Z)-5-(1,3-benzodioxol-5-ylmethylidene)-1-benzyl-1,3-diazinane-2,4,6-trione

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: 350.33

Molecular Weight (Monoisotopic): 350.0903

AlogP: 2.08

#Rotatable Bonds: 3

Polar Surface Area: 84.94

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.08

CX Basic pKa: ┄

CX LogP: 2.35

CX LogD: 1.87

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.68

Np Likeness Score: -0.87

References

1. Rechfeld F, Gruber P, Kirchmair J, Boehler M, Hauser N, Hechenberger G, Garczarczyk D, Lapa GB, Preobrazhenskaya MN, Goekjian P, Langer T, Hofmann J..  (2014)  Thienoquinolines as novel disruptors of the PKCε/RACK2 protein-protein interaction.,  57  (8): [PMID:24712764] [10.1021/jm401605c]

Source

Source(1):

• Scientific Literature