1,3-dimethyl-5-((naphthalen-1-ylamino)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA4093635

PubChem CID: 135902997

Max Phase: Preclinical

Molecular Formula: C17H15N3O3

Molecular Weight: 309.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)C(=CNc2cccc3ccccc23)C(=O)N(C)C1=O

Standard InChI:  InChI=1S/C17H15N3O3/c1-19-15(21)13(16(22)20(2)17(19)23)10-18-14-9-5-7-11-6-3-4-8-12(11)14/h3-10,18H,1-2H3

Standard InChI Key:  YOSHEBUFWAUMKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.4134  -15.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4134  -14.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228  -13.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322  -14.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322  -15.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228  -15.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5453  -15.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5435  -13.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2559  -14.2806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9671  -13.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9630  -13.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734  -12.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3827  -13.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228  -13.0528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7045  -15.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3829  -13.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6744  -14.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6803  -15.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3938  -15.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1030  -15.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0937  -14.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7059  -13.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228  -16.3339    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
  5  7  2  0
  4  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 16  1  0
 17 10  1  0
  3 14  2  0
  1 15  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 16  2  0
  2 22  1  0
  6 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093635

   ---

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: 309.33

Molecular Weight (Monoisotopic): 309.1113

AlogP: 2.19

#Rotatable Bonds: 2

Polar Surface Area: 69.72

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.75

CX Basic pKa: ┄

CX LogP: 1.46

CX LogD: 1.46

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -1.13

References

1. Pianovich NA, Dean M, Lassak A, Reiss K, Jursic BS..  (2017)  Anticancer potential of aminomethylidene-diazinanes I. Synthesis of arylaminomethylidene of diazinetriones and its cytotoxic effects tested in glioblastoma cells.,  25  (19): [PMID:28864149] [10.1016/j.bmc.2017.08.020]

Source

Source(1):

• Scientific Literature