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

ID: ALA2385913

PubChem CID: 71816845

Max Phase: Preclinical

Molecular Formula: C23H26N2O5

Molecular Weight: 410.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)N(C)C(=O)NC1c1ccc(OCc2ccccc2)c(OC)c1

Standard InChI:  InChI=1S/C23H26N2O5/c1-5-29-22(26)20-15(2)25(3)23(27)24-21(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:  HFWBZVFHPYLBTH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.2023  -18.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9161  -17.7753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6313  -18.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6279  -19.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423  -19.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0571  -19.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0531  -18.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3382  -17.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3327  -16.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6154  -16.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7728  -19.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7715  -20.2479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4830  -20.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1987  -20.2472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1983  -19.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4822  -19.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4823  -21.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9130  -19.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4818  -18.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7671  -17.7691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4871  -17.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882  -16.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739  -16.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0590  -16.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0630  -17.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779  -18.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9129  -20.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1961  -17.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9108  -18.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6251  -17.7677    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
 14 27  1  0
 19 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385913

   Ethyl 6-(3-methoxy-4-phenylmethoxyphenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-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: 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: 13.08

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 2.87

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.70

Np Likeness Score: -0.75

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