rac-ethyl 4-(3-methoxy-4-phenethoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ID: ALA2385909

Max Phase: Preclinical

Molecular Formula: C23H26N2O5

Molecular Weight: 410.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=O)NC1c1ccc(OCCc2ccccc2)c(OC)c1

Standard InChI:  InChI=1S/C23H26N2O5/c1-4-29-22(26)20-15(2)24-23(27)25-21(20)17-10-11-18(19(14-17)28-3)30-13-12-16-8-6-5-7-9-16/h5-11,14,21H,4,12-13H2,1-3H3,(H2,24,25,27)

Standard InChI Key:  PNCCOBRIMHWZEW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    5.1521   -4.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8659   -3.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5810   -4.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5776   -5.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2918   -5.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0067   -5.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0028   -4.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2879   -3.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2824   -2.9577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5651   -2.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7224   -5.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7210   -6.2596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4326   -6.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1482   -6.2589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1478   -5.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4318   -5.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4319   -7.4949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8625   -5.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4314   -4.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1456   -3.7801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7166   -3.7808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8603   -4.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5745   -3.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4369   -3.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7231   -4.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -3.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989   -4.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2997   -5.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199   -5.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7303   -5.0228    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  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:

   

   ALA2385909

   ---

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: 410.47

Molecular Weight (Monoisotopic): 410.1842

AlogP: 3.51

#Rotatable Bonds: 8

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: 2.94

CX LogD: 2.94

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -0.65

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