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

ID: ALA3621874

PubChem CID: 122191476

Max Phase: Preclinical

Molecular Formula: C21H21N5O3

Molecular Weight: 391.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccnc(-c2cn(C3CCN(C(=O)CCc4ccccc4)C3)nn2)c1

Standard InChI:  InChI=1S/C21H21N5O3/c27-20(7-6-15-4-2-1-3-5-15)25-11-9-17(13-25)26-14-19(23-24-26)18-12-16(21(28)29)8-10-22-18/h1-5,8,10,12,14,17H,6-7,9,11,13H2,(H,28,29)

Standard InChI Key:  BMDGMELYSLPYAP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  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
   -7.5110    2.8633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8282    2.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5529    0.6713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0654    0.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5805   -0.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1502   -1.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7482   -0.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1795   -2.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7493   -4.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7765   -5.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3435   -6.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8833   -7.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8560   -6.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2890   -4.7301    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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 23 21  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3621874

   ---

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: 391.43

Molecular Weight (Monoisotopic): 391.1644

AlogP: 2.44

#Rotatable Bonds: 6

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: 2.35

CX LogD: -1.00

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -1.30

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