4-(2-butyl-4-chloro-1H-imidazol-5-yl)-N-(3-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxamide

ID: ALA4476223

PubChem CID: 155538401

Max Phase: Preclinical

Molecular Formula: C19H21ClFN5O2

Molecular Weight: 405.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCc1nc(Cl)c(C2NC(=O)NC(C)=C2C(=O)Nc2cccc(F)c2)[nH]1

Standard InChI:  InChI=1S/C19H21ClFN5O2/c1-3-4-8-13-24-16(17(20)25-13)15-14(10(2)22-19(28)26-15)18(27)23-12-7-5-6-11(21)9-12/h5-7,9,15H,3-4,8H2,1-2H3,(H,23,27)(H,24,25)(H2,22,26,28)

Standard InChI Key:  FLUCTJIXNVBQKY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   13.9752  -12.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9719  -11.8170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2632  -11.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5579  -11.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5612  -12.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2699  -13.0492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8451  -11.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8418  -10.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1398  -11.8345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4311  -11.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7257  -11.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171  -11.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0096  -10.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7150  -10.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236  -10.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6880  -13.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8559  -13.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6570   -9.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8399   -9.3399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5923  -10.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2558  -10.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9147  -10.1115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8573  -10.2175    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.1353   -8.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7982   -7.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2723   -7.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9353   -6.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3051  -11.8539    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  7  9  1  0
  4  7  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
  9 10  1  0
  1 16  2  0
  5 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 18 22  1  0
 20 23  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 18 24  1  0
  3 21  1  0
 12 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476223

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 405.86

Molecular Weight (Monoisotopic): 405.1368

AlogP: 3.81

#Rotatable Bonds: 6

Polar Surface Area: 98.91

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.67

CX Basic pKa: 4.36

CX LogP: 2.42

CX LogD: 2.42

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: -1.66

References

1. Desai NC, Trivedi AR, Khedkar VM..  (2016)  Preparation, biological evaluation and molecular docking study of imidazolyl dihydropyrimidines as potential Mycobacterium tuberculosis dihydrofolate reductase inhibitors.,  26  (16): [PMID:27397497] [10.1016/j.bmcl.2016.06.082]

Source

Source(1):

• Scientific Literature