rac-ethyl 4-(2-chloro-4-(2-chlorobenzyloxy)-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ID: ALA2385748

Max Phase: Preclinical

Molecular Formula: C22H22Cl2N2O5

Molecular Weight: 465.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=O)NC1c1cc(OC)c(OCc2ccccc2Cl)cc1Cl

Standard InChI:  InChI=1S/C22H22Cl2N2O5/c1-4-30-21(27)19-12(2)25-22(28)26-20(19)14-9-17(29-3)18(10-16(14)24)31-11-13-7-5-6-8-15(13)23/h5-10,20H,4,11H2,1-3H3,(H2,25,26,28)

Standard InChI Key:  KNFVETGXHZPMRV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    4.9023  -28.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6162  -28.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3313  -28.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3279  -29.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0422  -30.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7570  -29.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7531  -28.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0382  -28.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0326  -27.6129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3154  -27.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4727  -30.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4714  -30.9150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1830  -31.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8988  -30.9143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8984  -30.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1822  -29.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1823  -32.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6131  -29.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1818  -28.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8960  -28.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4671  -28.4361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6107  -28.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3250  -28.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0431  -30.9136    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1872  -28.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1881  -27.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4738  -27.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7590  -27.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630  -28.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4779  -28.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4825  -29.6846    0.0000 Cl  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
  5 24  1  0
  1 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
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385748

   ---

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: 465.33

Molecular Weight (Monoisotopic): 464.0906

AlogP: 4.77

#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: 12.30

CX Basic pKa: ┄

CX LogP: 3.86

CX LogD: 3.86

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -1.08

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]

Source

Source(1):

• Scientific Literature