US9320722, 13

ID: ALA4109466

PubChem CID: 24661959

Max Phase: Preclinical

Molecular Formula: C18H22N4O5S

Molecular Weight: 406.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNS(=O)(=O)c1ccc(Nc2ccc(NC(=O)CC(C)C)cc2)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C18H22N4O5S/c1-12(2)10-18(23)21-14-6-4-13(5-7-14)20-16-9-8-15(28(26,27)19-3)11-17(16)22(24)25/h4-9,11-12,19-20H,10H2,1-3H3,(H,21,23)

Standard InChI Key:  XELCNUCXLHKOSD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    3.6390   -3.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -3.0012    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
    3.6378   -0.9001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6383   -2.0999    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765    7.5048    0.0000 N   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 C   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
    0.0452   11.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747    9.8883    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
  3  4  2  0
  3  5  2  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 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  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 14 22  1  0
 22 23  2  0
 23 11  1  0
  9 24  1  0
 24 25  2  0
 25  6  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4109466

   CB29 (derivative 13)

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: 406.46

Molecular Weight (Monoisotopic): 406.1311

AlogP: 3.23

#Rotatable Bonds: 8

Polar Surface Area: 130.44

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.07

CX Basic pKa: ┄

CX LogP: 4.15

CX LogD: 4.15

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: -1.84

References

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

Source

Source(1):

• BindingDB Database