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

ID: ALA2385911

PubChem CID: 50887893

Max Phase: Preclinical

Molecular Formula: C21H22N2O4

Molecular Weight: 366.42

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H22N2O4/c1-13-19(14(2)24)20(23-21(25)22-13)16-9-10-17(18(11-16)26-3)27-12-15-7-5-4-6-8-15/h4-11,20H,12H2,1-3H3,(H2,22,23,25)

Standard InChI Key:  IUAPANPDPMBIST-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    5.2022  -11.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9160  -10.8748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6312  -11.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6277  -12.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3421  -12.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0569  -12.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0529  -11.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3381  -10.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3325  -10.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6152   -9.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7726  -12.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7712  -13.3473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4828  -13.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1985  -13.3466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1981  -12.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4820  -12.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4821  -14.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9127  -12.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4816  -11.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7669  -10.8685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4870  -10.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4880  -10.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7738   -9.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589  -10.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0629  -10.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778  -11.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2027  -10.8639    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
 19 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385911

   5-acetyl-4-(3-methoxy-4-phenylmethoxyphenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-one

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: 366.42

Molecular Weight (Monoisotopic): 366.1580

AlogP: 3.49

#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: 12.64

CX Basic pKa: ┄

CX LogP: 2.24

CX LogD: 2.24

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -0.60

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