N-((2-(4-fluorophenyl)-3-(2-((S)-1-phenylethyl)pyrimidin-4-yl)H-imidazo[1,2-a]pyridin-7-yl)methyl)acetamide

ID: ALA375649

PubChem CID: 44419856

Max Phase: Preclinical

Molecular Formula: C28H24FN5O

Molecular Weight: 465.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NCc1ccn2c(-c3ccnc([C@@H](C)c4ccccc4)n3)c(-c3ccc(F)cc3)nc2c1

Standard InChI:  InChI=1S/C28H24FN5O/c1-18(21-6-4-3-5-7-21)28-30-14-12-24(32-28)27-26(22-8-10-23(29)11-9-22)33-25-16-20(13-15-34(25)27)17-31-19(2)35/h3-16,18H,17H2,1-2H3,(H,31,35)/t18-/m0/s1

Standard InChI Key:  MVFOODAIQUTQDQ-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  1  0  0  0  0  0999 V2000
   -1.4431   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4443   -2.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7294   -2.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0130   -2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159   -1.6463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312   -1.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7337   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0205    0.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4485    0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1634    1.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8776    0.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725   -0.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570   -0.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7021   -2.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7865   -3.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5946   -3.8813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498   -2.5533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0001   -3.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -2.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0552   -2.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999   -1.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1731   -4.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6070   -4.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2200   -4.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492   -5.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598   -5.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3498   -5.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6619   -5.9145    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8617   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4156   -2.6480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2220   -2.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7760   -3.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745   -1.6885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
 17 19  2  0
 18 15  1  0
  7  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
 23 18  1  0
  5  6  2  0
 16 24  1  0
 11 12  2  0
 24 25  2  0
  6  1  1  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
  1  2  2  0
 27 28  1  0
 13 14  2  0
 28 29  2  0
 29 24  1  0
 14  9  1  0
 27 30  1  0
  6  7  1  0
 21 31  1  0
  4 15  1  0
 31 32  1  0
 16 17  1  0
 32 33  1  0
  3  4  2  0
 33 34  1  0
  7  8  1  6
 33 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA375649

   N-[[2-(4-fluorophenyl)-3-[2-[(1S)-1-phenylethyl]pyrimidin-4-yl]imidazo[1,2-a]pyridin-7-yl]methyl]acetamide

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: 465.53

Molecular Weight (Monoisotopic): 465.1965

AlogP: 5.39

#Rotatable Bonds: 6

Polar Surface Area: 72.18

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.28

CX LogP: 4.99

CX LogD: 4.99

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.37

Np Likeness Score: -1.24

References

1. Feng D, Fisher M, Liang GB, Qian X, Brown C, Gurnett A, Leavitt PS, Liberator PA, Mathew J, Misura A, Samaras S, Tamas T, Schmatz DM, Wyvratt M, Biftu T..  (2006)  Synthesis and SAR of 2-(4-fluorophenyl)-3-pyrimidin-4-ylimidazo[1,2-a]pyridine derivatives as anticoccidial agents.,  16  (23): [PMID:17000105] [10.1016/j.bmcl.2006.08.127]

Source

Source(1):

• Scientific Literature