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

ID: ALA2385912

Max Phase: Preclinical

Molecular Formula: C21H21ClN2O4

Molecular Weight: 400.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C2NC(=O)NC(C)=C2C(C)=O)ccc1OCc1ccccc1Cl

Standard InChI:  InChI=1S/C21H21ClN2O4/c1-12-19(13(2)25)20(24-21(26)23-12)14-8-9-17(18(10-14)27-3)28-11-15-6-4-5-7-16(15)22/h4-10,20H,11H2,1-3H3,(H2,23,24,26)

Standard InChI Key:  DFUVBJKPZRTNNE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   17.5607  -11.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2745  -11.1373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9897  -11.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9863  -12.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7006  -12.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4154  -12.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4115  -11.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6966  -11.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6911  -10.3079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9738   -9.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1311  -12.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1297  -13.6098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8414  -14.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5570  -13.6091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5566  -12.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8404  -12.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8405  -14.8452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2713  -12.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8400  -11.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1254  -11.1310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8456  -11.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8466  -10.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1323   -9.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4175  -10.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4214  -11.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1363  -11.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1409  -12.3795    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.5612  -11.1264    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  2  0
  1 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 26 27  1  0
 19 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385912

   ---

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: 400.86

Molecular Weight (Monoisotopic): 400.1190

AlogP: 4.14

#Rotatable Bonds: 6

Polar Surface Area: 76.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: ┄

CX LogP: 2.85

CX LogD: 2.85

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.76

Np Likeness Score: -0.95

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