4-(4-Fluoro-phenyl)-6-methyl-2-pentylsulfanyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester

ID: ALA473165

PubChem CID: 25187364

Max Phase: Preclinical

Molecular Formula: C19H25FN2O2S

Molecular Weight: 364.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCSC1=NC(c2ccc(F)cc2)C(C(=O)OCC)=C(C)N1

Standard InChI:  InChI=1S/C19H25FN2O2S/c1-4-6-7-12-25-19-21-13(3)16(18(23)24-5-2)17(22-19)14-8-10-15(20)11-9-14/h8-11,17H,4-7,12H2,1-3H3,(H,21,22)

Standard InChI Key:  CXDSTOGDGKZFFF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -2.4724    2.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4724    1.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7594    1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0464    1.6054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0464    2.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7594    2.8458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1892    2.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874    1.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8993    1.6034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1862    0.3640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6142    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3303    1.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297    2.8396    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3846    2.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013    2.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7599    0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773   -0.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -1.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0466   -0.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0438   -0.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8114    2.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282    2.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2425    2.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7601   -2.1060    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  5 13  1  0
 13 14  1  0
  1  7  1  0
 14 15  1  0
  1  2  2  0
  2  8  1  0
 16 17  2  0
  1  6  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
 19 21  1  0
 20 16  1  0
  3 16  1  0
  2  3  1  0
  8 10  2  0
 20 21  2  0
  3  4  1  0
 15 22  1  0
  9 11  1  0
 22 23  1  0
  4  5  2  0
 23 24  1  0
 11 12  1  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA473165

   Ethyl 4-(4-fluorophenyl)-6-methyl-2-pentylsulfanyl-1,4-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: 364.49

Molecular Weight (Monoisotopic): 364.1621

AlogP: 4.59

#Rotatable Bonds: 7

Polar Surface Area: 50.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.27

CX LogP: 4.88

CX LogD: 4.88

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.57

Np Likeness Score: -0.98

References

1. Singh BK, Mishra M, Saxena N, Yadav GP, Maulik PR, Sahoo MK, Gaur RL, Murthy PK, Tripathi RP..  (2008)  Synthesis of 2-sulfanyl-6-methyl-1,4-dihydropyrimidines as a new class of antifilarial agents.,  43  (12): [PMID:18339456] [10.1016/j.ejmech.2008.01.038]

Source

Source(1):

• Scientific Literature