US9320722, 19

ID: ALA4115065

PubChem CID: 17560769

Max Phase: Preclinical

Molecular Formula: C22H29N5O5S

Molecular Weight: 475.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)NS(=O)(=O)c1ccc(NC2CCN(CC(=O)Nc3ccccc3)CC2)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C22H29N5O5S/c1-16(2)25-33(31,32)19-8-9-20(21(14-19)27(29)30)23-18-10-12-26(13-11-18)15-22(28)24-17-6-4-3-5-7-17/h3-9,14,16,18,23,25H,10-13,15H2,1-2H3,(H,24,28)

Standard InChI Key:  HZIAVAFBOJTXSF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    6.2384   -0.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1988   -1.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1984   -2.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6377   -2.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -2.7004    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
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8916    3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8864    5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847    6.0040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765    7.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2731    8.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370    7.6435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2648    9.7497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   10.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490   11.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532   12.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471   11.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367   10.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325    9.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883    5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935    3.7495    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
   -2.5972   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955   -2.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 16 27  1  0
 27 28  1  0
 28 13  1  0
 11 29  1  0
 29 30  2  0
 30  8  1  0
 29 31  1  0
 31 32  2  0
 31 33  1  0
M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4115065

   CB29 (derivative 19)

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: 475.57

Molecular Weight (Monoisotopic): 475.1889

AlogP: 2.80

#Rotatable Bonds: 9

Polar Surface Area: 133.68

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.19

CX Basic pKa: 6.70

CX LogP: 2.58

CX LogD: 2.50

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -2.24

References

1.  (2016)  Regulators of aldehyde dehydrogenase ALDH3A1 and related therapeutic methods, 

Source

Source(1):

• BindingDB Database