2-Amino-N-[4-[[3-(1-methylpyrazol-4-yl)-1H-indol-5-yl]oxy]phenyl]acetamide

ID: ALA3422679

Max Phase: Preclinical

Molecular Formula: C19H18N6O2

Molecular Weight: 362.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2n[nH]c3ccc(Oc4ccc(NC(=O)CN)cc4)cc23)cn1

Standard InChI:  InChI=1S/C19H18N6O2/c1-25-11-12(10-21-25)19-16-8-15(6-7-17(16)23-24-19)27-14-4-2-13(3-5-14)22-18(26)9-20/h2-8,10-11H,9,20H2,1H3,(H,22,26)(H,23,24)

Standard InChI Key:  WBKFBMOXKGKWEK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187    1.4919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267    2.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282    3.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9331    5.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6365    5.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350    5.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3301    3.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6383    7.4936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399    8.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2998    7.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3417    9.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036   10.3491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    2.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751    3.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    5.0280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.4644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243    2.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0517    6.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  1 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 22  1  0
  9 22  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3422679

   ---

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: 362.39

Molecular Weight (Monoisotopic): 362.1491

AlogP: 2.65

#Rotatable Bonds: 5

Polar Surface Area: 110.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.63

CX Basic pKa: 7.98

CX LogP: 1.57

CX LogD: 0.89

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.73

References

1. Boyd S, Brookfield JL, Critchlow SE, Cumming IA, Curtis NJ, Debreczeni J, Degorce SL, Donald C, Evans NJ, Groombridge S, Hopcroft P, Jones NP, Kettle JG, Lamont S, Lewis HJ, MacFaull P, McLoughlin SB, Rigoreau LJ, Smith JM, St-Gallay S, Stock JK, Turnbull AP, Wheatley ER, Winter J, Wingfield J..  (2015)  Structure-Based Design of Potent and Selective Inhibitors of the Metabolic Kinase PFKFB3.,  58  (8): [PMID:25849762] [10.1021/acs.jmedchem.5b00352]

Source

Source(1):

• Scientific Literature