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

ID: ALA4585882

PubChem CID: 155566890

Max Phase: Preclinical

Molecular Formula: C18H20N2O6S

Molecular Weight: 392.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COCCOC(=O)C1=C(C)NC(=S)N(C(C)=O)C1c1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C18H20N2O6S/c1-10-15(17(22)24-7-6-23-3)16(20(11(2)21)18(27)19-10)12-4-5-13-14(8-12)26-9-25-13/h4-5,8,16H,6-7,9H2,1-3H3,(H,19,27)

Standard InChI Key:  UAMXWPNQNSFOEW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   26.6758  -23.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6758  -24.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3878  -24.6049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0999  -24.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0999  -23.3715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3878  -22.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8138  -24.6100    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.9619  -24.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3882  -22.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1044  -21.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6728  -20.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6761  -21.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3897  -20.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0999  -20.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7122  -20.3464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3804  -19.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5631  -19.6781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9601  -22.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9576  -22.1361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2468  -23.3757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5311  -22.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8156  -22.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5288  -23.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8180  -22.1361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8178  -23.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1021  -22.9695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3889  -23.3841    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
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4585882

   ---

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: 392.43

Molecular Weight (Monoisotopic): 392.1042

AlogP: 1.66

#Rotatable Bonds: 5

Polar Surface Area: 86.33

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.34

CX LogD: 1.34

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.46

Np Likeness Score: -0.56

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