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

ID: ALA4467584

PubChem CID: 155532833

Max Phase: Preclinical

Molecular Formula: C19H22N2O5S

Molecular Weight: 390.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H22N2O5S/c1-10(2)8-24-18(23)16-11(3)20-19(27)21(12(4)22)17(16)13-5-6-14-15(7-13)26-9-25-14/h5-7,10,17H,8-9H2,1-4H3,(H,20,27)

Standard InChI Key:  MSHJOFCKIQEXTF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   16.3337  -23.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3337  -24.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0457  -24.9339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7578  -24.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7578  -23.7006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0457  -23.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4717  -24.9391    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.6198  -24.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0463  -22.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7623  -22.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3308  -21.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3340  -22.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0477  -20.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7578  -21.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3702  -20.6755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0384  -19.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2211  -20.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6180  -23.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6156  -22.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9047  -23.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1890  -23.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4735  -23.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1868  -23.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4759  -22.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4758  -23.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7601  -23.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4782  -24.5340    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  1  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4467584

   ---

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: 390.46

Molecular Weight (Monoisotopic): 390.1249

AlogP: 2.67

#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: 2.63

CX LogD: 2.63

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -0.45

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