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

ID: ALA2385914

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)N(C)C1c1ccc(OCc2ccccc2)c(OC)c1

Standard InChI:  InChI=1S/C23H26N2O5/c1-5-29-22(26)20-15(2)24-23(27)25(3)21(20)17-11-12-18(19(13-17)28-4)30-14-16-9-7-6-8-10-16/h6-13,21H,5,14H2,1-4H3,(H,24,27)

Standard InChI Key:  HISJWAKJMJWQPT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   16.6444  -18.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3583  -17.9753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0735  -18.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0700  -19.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7843  -19.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4992  -19.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4953  -18.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7804  -17.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7748  -17.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0575  -16.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2149  -19.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2135  -20.4479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9252  -20.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6409  -20.4472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6405  -19.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9244  -19.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9244  -21.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3552  -19.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9240  -18.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6382  -17.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2092  -17.9691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3529  -18.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9293  -17.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9303  -17.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2160  -16.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5011  -17.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5051  -17.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2199  -18.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0672  -17.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4988  -20.8600    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
  1 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 22 29  1  0
 12 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385914

   ---

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: 3.81

#Rotatable Bonds: 7

Polar Surface Area: 77.10

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.69

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 2.87

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.70

Np Likeness Score: -0.59

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