6-chloro-5-((3-chloro-2-cyclopropylphenoxy)methyl)-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one

ID: ALA5282728

Max Phase: Preclinical

Molecular Formula: C21H16Cl2N4O2

Molecular Weight: 427.29

Names and Identifiers

Canonical SMILES:  O=c1c(Cl)c(COc2cccc(Cl)c2C2CC2)[nH]c2nc(-c3ccccc3)nn12

Standard InChI:  InChI=1S/C21H16Cl2N4O2/c22-14-7-4-8-16(17(14)12-9-10-12)29-11-15-18(23)20(28)27-21(24-15)25-19(26-27)13-5-2-1-3-6-13/h1-8,12H,9-11H2,(H,24,25,26)

Standard InChI Key:  HGXDDSUVIVWHNN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.2706    1.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4412    0.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4412   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2687   -0.6166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852   -0.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7730    0.8759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -0.4645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2599    0.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0883    0.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5026   -0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3284   -0.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7426    0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3319    0.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5041    0.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706    1.8605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585   -0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8758   -0.2048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5931   -0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3106   -0.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0253   -0.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0253   -1.4470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3124   -1.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5931   -1.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3106    0.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7426   -0.2044    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1585    1.0345    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7255    1.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    1.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  1  0
  1  7  1  0
  6  8  2  0
  8  9  1  0
  9  7  2  0
  9 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 10 15  1  0
  2 16  2  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 19 24  1  0
 20 25  1  0
 21 26  1  0
  3 27  1  0
 28 25  1  0
 28 29  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282728

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 427.29

Molecular Weight (Monoisotopic): 426.0650

AlogP: 4.85

#Rotatable Bonds: 5

Polar Surface Area: 72.28

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: 6.21

CX LogD: 6.21

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -0.99

References

1. Floresta G, Pistarà V, Amata E, Dichiara M, Marrazzo A, Prezzavento O, Rescifina A..  (2017)  Adipocyte fatty acid binding protein 4 (FABP4) inhibitors. A comprehensive systematic review.,  138  [PMID:28738306] [10.1016/j.ejmech.2017.07.022]

Source

Source(1):

• Scientific Literature