rac-Ethyl 4-(4-(benzyloxy)-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ID: ALA2385908

Max Phase: Preclinical

Molecular Formula: C22H24N2O5

Molecular Weight: 396.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=O)NC1c1ccc(OCc2ccccc2)c(OC)c1

Standard InChI:  InChI=1S/C22H24N2O5/c1-4-28-21(25)19-14(2)23-22(26)24-20(19)16-10-11-17(18(12-16)27-3)29-13-15-8-6-5-7-9-15/h5-12,20H,4,13H2,1-3H3,(H2,23,24,26)

Standard InChI Key:  NQQNHUALWFENLG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   15.8819  -28.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5956  -28.3464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3108  -28.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3074  -29.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0218  -29.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7366  -29.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7326  -28.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0178  -28.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0122  -27.5170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2949  -27.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4523  -29.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4510  -30.8191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1625  -31.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8782  -30.8183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8778  -29.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1617  -29.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1618  -32.0544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5925  -29.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1613  -28.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8756  -28.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4466  -28.3402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5903  -28.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3046  -28.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1667  -28.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1677  -27.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4534  -27.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7385  -27.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7425  -28.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4573  -28.7636    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  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  8  9  1  0
  9 10  1  0
 11  6  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 13 17  2  0
 15 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
  1 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385908

   ---

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: 396.44

Molecular Weight (Monoisotopic): 396.1685

AlogP: 3.47

#Rotatable Bonds: 7

Polar Surface Area: 85.89

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.57

CX Basic pKa: ┄

CX LogP: 2.65

CX LogD: 2.65

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -0.75

References

1. Dubernet M, Duguet N, Colliandre L, Berini C, Helleboid S, Bourotte M, Daillet M, Maingot L, Daix S, Delhomel JF, Morin-Allory L, Routier S, Walczak R..  (2013)  Identification of New Nonsteroidal RORα Ligands; Related Structure-Activity Relationships and Docking Studies.,  4  (6): [PMID:24900700] [10.1021/ml300471d]

2. Li Z, Liu T, He X, Bai C..  (2022)  The evolution paths of some reprehensive scaffolds of RORγt modulators, a perspective from medicinal chemistry.,  228  [PMID:34776280] [10.1016/j.ejmech.2021.113962]

Source

Source(1):

• Scientific Literature