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

ID: ALA2385916

PubChem CID: 2855158

Max Phase: Preclinical

Molecular Formula: C28H28N2O5

Molecular Weight: 472.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C2NC(=O)NC(C)=C2C(=O)OCCc2ccccc2)ccc1OCc1ccccc1

Standard InChI:  InChI=1S/C28H28N2O5/c1-19-25(27(31)34-16-15-20-9-5-3-6-10-20)26(30-28(32)29-19)22-13-14-23(24(17-22)33-2)35-18-21-11-7-4-8-12-21/h3-14,17,26H,15-16,18H2,1-2H3,(H2,29,30,32)

Standard InChI Key:  IPNCGVLLVXNTHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
    4.4397   -4.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1536   -4.1455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8686   -4.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8653   -5.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5796   -5.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2944   -5.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2904   -4.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5755   -4.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5700   -3.3161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8528   -2.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0100   -5.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0087   -6.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7203   -7.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4361   -6.6173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4355   -5.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7195   -5.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7196   -7.8535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1503   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7191   -4.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4333   -4.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0044   -4.1392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1480   -4.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7245   -4.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -3.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0112   -2.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2965   -3.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004   -4.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153   -4.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8623   -4.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8619   -3.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5779   -2.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5778   -2.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8626   -1.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1459   -2.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1495   -2.9043    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
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385916

   2-Phenylethyl 4-[4-(benzyloxy)-3-methoxyphenyl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

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: 472.54

Molecular Weight (Monoisotopic): 472.1998

AlogP: 4.69

#Rotatable Bonds: 9

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: 12.59

CX Basic pKa: ┄

CX LogP: 4.31

CX LogD: 4.31

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.44

Np Likeness Score: -0.56

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