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

ID: ALA2385910

PubChem CID: 71816843

Max Phase: Preclinical

Molecular Formula: C24H28N2O5

Molecular Weight: 424.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=O)NC1c1ccc(OCCCc2ccccc2)c(OC)c1

Standard InChI:  InChI=1S/C24H28N2O5/c1-4-30-23(27)21-16(2)25-24(28)26-22(21)18-12-13-19(20(15-18)29-3)31-14-8-11-17-9-6-5-7-10-17/h5-7,9-10,12-13,15,22H,4,8,11,14H2,1-3H3,(H2,25,26,28)

Standard InChI Key:  SLTUDWRZOIMYHS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   17.6944   -4.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4083   -3.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1234   -4.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1200   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8343   -5.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5491   -4.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5452   -4.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8303   -3.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8247   -2.9370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1075   -2.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2648   -5.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2635   -6.2390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9750   -6.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6908   -6.2383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6904   -5.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9742   -4.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9743   -7.4744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4051   -5.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9738   -4.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6881   -3.7595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2591   -3.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4028   -4.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1171   -3.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9793   -3.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2654   -4.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5502   -3.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5515   -2.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8371   -2.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1224   -2.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1263   -3.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8412   -4.1881    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
 22 23  1  0
  1 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385910

   ethyl 4-[3-methoxy-4-(3-phenylpropoxy)phenyl]-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-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: 424.50

Molecular Weight (Monoisotopic): 424.1998

AlogP: 3.90

#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: 3.38

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -0.66

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