rac-2-[1-(1-Benzoylpiperidin-3-yl)-1H-1,2,3-triazol-4-yl]isonicotinic acid

ID: ALA3621878

PubChem CID: 122191480

Max Phase: Preclinical

Molecular Formula: C20H19N5O3

Molecular Weight: 377.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccnc(-c2cn(C3CCCN(C(=O)c4ccccc4)C3)nn2)c1

Standard InChI:  InChI=1S/C20H19N5O3/c26-19(14-5-2-1-3-6-14)24-10-4-7-16(12-24)25-13-18(22-23-25)17-11-15(20(27)28)8-9-21-17/h1-3,5-6,8-9,11,13,16H,4,7,10,12H2,(H,27,28)

Standard InChI Key:  BFLBQNQXHXJNHU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0351   -3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -3.5993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7390    2.9810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2067    3.2905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9546    1.9903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9492    0.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4469    1.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4153    2.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8906    2.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3937    1.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4213    0.1438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9460    0.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9217   -1.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9473   -2.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1016   -1.4900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4453   -3.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4691   -4.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9947   -4.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4966   -3.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4728   -2.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  7  9  2  0
  6  7  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 10  2  0
  4 10  1  0
 13 15  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3621878

   ---

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: 377.40

Molecular Weight (Monoisotopic): 377.1488

AlogP: 2.52

#Rotatable Bonds: 4

Polar Surface Area: 101.21

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.58

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: -0.90

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -1.41

References

1. England KS, Tumber A, Krojer T, Scozzafava G, Ng SS, Daniel M, Szykowska A, Che K, von Delft F, Burgess-Brown NA, Kawamura A, Schofield CJ, Brennan PE..  (2014)  Optimisation of a triazolopyridine based histone demethylase inhibitor yields a potent and selective KDM2A (FBXL11) inhibitor.,  5  (12): [PMID:26682034] [10.1039/c4md00291a]

Source

Source(1):

• Scientific Literature