US9428478, TG6-199

ID: ALA3962738

PubChem CID: 71116233

Max Phase: Preclinical

Molecular Formula: C20H21N3O3

Molecular Weight: 351.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N2CCN(C(=O)c3cc4cc(O)ccc4[nH]3)CC2)cc1

Standard InChI:  InChI=1S/C20H21N3O3/c1-26-17-5-2-15(3-6-17)22-8-10-23(11-9-22)20(25)19-13-14-12-16(24)4-7-18(14)21-19/h2-7,12-13,21,24H,8-11H2,1H3

Standard InChI Key:  GNDNVGJPNUTBMV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -3.9394  -13.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395  -13.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9798  -12.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4798  -12.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2768  -10.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4666   -9.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9666   -9.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232  -10.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2883   -8.3139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7883   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428   -7.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974   -5.7210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2973   -5.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4572   -7.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497   -4.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -4.4245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    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
    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
    0.0000    2.7000    0.0000 O   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
    0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  9  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 19  1  0
 25 26  1  0
 26 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3962738

   (5-hydroxy-1H-indol-2-yl)-[4-(4-methoxyphenyl)piperazin-1-yl]methanone

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: 351.41

Molecular Weight (Monoisotopic): 351.1583

AlogP: 2.84

#Rotatable Bonds: 3

Polar Surface Area: 68.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.56

CX Basic pKa: 3.99

CX LogP: 2.57

CX LogD: 2.56

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.76

Np Likeness Score: -1.00

References

1.  (2016)  Piperazine derivatives, compositions, and uses related thereto, 

Source

Source(1):

• BindingDB Database