(+/-)-Benzyl 3-acetyl-4-(benzo[d][1,3]dioxol-5-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ID: ALA4473803

PubChem CID: 155536624

Max Phase: Preclinical

Molecular Formula: C22H20N2O5S

Molecular Weight: 424.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)N1C(=S)NC(C)=C(C(=O)OCc2ccccc2)C1c1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C22H20N2O5S/c1-13-19(21(26)27-11-15-6-4-3-5-7-15)20(24(14(2)25)22(30)23-13)16-8-9-17-18(10-16)29-12-28-17/h3-10,20H,11-12H2,1-2H3,(H,23,30)

Standard InChI Key:  QZLXDLKZWFZJOP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   38.9728  -23.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9728  -23.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6848  -24.2638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.3969  -23.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3969  -23.0303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6848  -22.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1108  -24.2689    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.2589  -24.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6853  -21.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4014  -21.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9699  -20.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9730  -21.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6867  -20.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3970  -20.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0093  -20.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.6774  -19.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8602  -19.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.2571  -22.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2547  -21.7949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5438  -23.0345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8281  -22.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1126  -22.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8259  -23.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1150  -21.7949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1147  -23.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3998  -22.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6869  -23.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6890  -23.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4097  -24.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1196  -23.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  2  0
  2  8  1  0
  9 10  2  0
 10 14  1  0
 13 11  1  0
 11 12  2  0
 12  9  1  0
  6  9  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  1 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
  5 22  1  0
 22 23  1  0
 22 24  2  0
 21 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4473803

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 424.48

Molecular Weight (Monoisotopic): 424.1093

AlogP: 3.21

#Rotatable Bonds: 4

Polar Surface Area: 77.10

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.60

Np Likeness Score: -0.47

References

1. Tawfik HO, El-Moselhy TF, El-Din NS, El-Hamamsy MH..  (2019)  Design, synthesis, and bioactivity of dihydropyrimidine derivatives as kinesin spindle protein inhibitors.,  27  (23): [PMID:31648875] [10.1016/j.bmc.2019.115126]

Source

Source(1):

• Scientific Literature